Hilton Head Island

No. 241

Panoramic Views and Luxurious Features - Stunning Oceanfront Villa

Condo

1 bedroom sleeps 4 private pool

DIRECT OCEANFRONT TOP-FLOOR CORNER VILLA WITH PANORAMIC OCEAN, BEACH, AND MARSH VIEWS Experience breathtaking views from this stunning third-floor corner villa, offering panoramic vistas of the Atlantic Ocean, beach, and surrounding marshlands. This spacious, one-of-a-kind villa has been completely remodeled with luxurious upgrades and modern coastal charm throughout. Special features include a king-size bed, an expanded living area, smooth ceilings with recessed lighting, and elegant quartz finishes featured on countertops, window sills, and shelving. The bright, open-concept floor plan creates the perfect setting for a relaxing beach getaway.

Check rates on Whimstay →

No. 242

Ocean and Marsh View Home with private pool, dog friendly, beachfront

House

6 bedroom sleeps 16 private pool

Collier Court 4 Welcome to your dream getaway in Hilton Head, SC! Just 50 feet from the beach path, this stunning house offers breathtaking views of both the ocean and marsh, making it the perfect retreat for families and friends. With 6 spacious bedrooms and 6.5 bathrooms, each equipped with its own private bathroom, everyone can enjoy their own space while still being together. The residence boasts three ocean-view porches where you can sip your morning coffee or unwind with a glass of wine as the sun sets. Dive into the heated private pool for a refreshing swim or challenge your loved ones to a game of ping pong. The home is dog-friendly, so your furry companions can join in on the fun!

Check rates on Whimstay →

No. 243

Stunning oceanfront home with pool, private boardwalk, decks, & elevator

House

6 bedroom sleeps 16 private pool

Dune Lane 105 If you’ve been planning a group getaway to Hilton Head but haven’t yet found the perfect place, stop scrolling - here it is. With an unbeatable oceanfront location just two miles from Coligny Beach Park, beach access via your own boardwalk, two enormous wraparound decks, a pool, and stunning ocean views from the main areas of the home, you’ll feel like you’ve stumbled into your own private paradise. Thoughtful upgrades include a remodeled kitchen with all new top-of-the-line appliances, new countertops, and brand-new cabinets.

Check rates on Whimstay →

No. 244

Stunning Oceanfront Hideaway with Private Pool, Deck, and Yard - Dogs Welcome

House

5 bedroom sleeps 14 private pool

Paradise *Please read our important pool heat information to help you have the best vacation possible!* This property has a pool that can be heated between Labor Day and Memorial Day for an additional fee of $69/night. You MUST notify management at least seven days in advance of your arrival if you would like to purchase pool heat. If the outside temperature is colder than 55 degrees, the pool will not be able to maintain a warmer temperature. If the pool does not reach your desired temperature but is still warming, refunds will NOT be given. Enjoy the tropical landscape and the first floor elevated balcony ocean views, which span the entire width of this dog-friendly home.

Check rates on Whimstay →

No. 245

Beachfront beauty with pool access fireplaces, jetted tub, balconies, & WD

House

5 bedroom sleeps 10 shared pool

Sea Pointe This elegant five-bedroom home is just steps away from Singleton Beach and the shared community pool! Bring the whole family and create sun-soaked, lifelong memories in Hilton Head. When your toes aren't dug into the warm white sand, check out Folly Field Beach Park, the Arts Center of Coastal Carolina, the Coastal Discovery Museum, the Harbour Town Lighthouse, and Harbour Town Golf Links. When you're ready to relax, your home away from home will welcome you with open arms! Kick up your feet and tune into your favorite TV shows and movies in the spacious living room. When extra warmth is needed, turn on the gas fireplace.

Check rates on Whimstay →

No. 246

Beachfront home with private pool, expansive deck & breathtaking views

House

5 bedroom sleeps 12 private pool

Dunes House Enjoy life at the beach at Dunes House! This home has impressive views of the beach and the Atlantic Ocean. The open living space on the second floor has living, dining, and a well-equipped kitchen that all look out to the Atlantic. Enjoy a cookout on the large deck off of the second floor or unwind on the screened porch. The first floor has a second living area leading out to the pool that can be heated for an additional fee. Surf and sand are a few steps away using the beach path next to the home. The modern Coligny Beach Park area provides benches, swings, restrooms, and changing rooms for beachgoers.

Check rates on Whimstay →

No. 247

Endless Tides - Marshfront Lands End Retreat. Pool Across Street. 500 Feet to Beach Access

Townhouse

4 bedroom sleeps 8 shared pool

"Endless Tides - Marsh Views, Ocean Glimpses, Steps to the Beach & Pool. Hilton Head Island, SC 29928 Welcome to Endless Tides, a beautifully positioned 4-bedroom, 3-bath coastal retreat tucked inside the exclusive gated community of Lands End within Sea Pines. Perfectly situated between Braddock Cove and the Atlantic Ocean, this attached single-family home offers expansive marsh views from nearly every rear-facing room, ocean glimpses from the upper level, the community pool directly across the street, and beach access less than 500 feet away. The location is truly special.

Check rates on Whimstay →

No. 248

Oceanfront Villa with kitchen, balcony, patio shared pool and trails

Villa

4 bedroom sleeps 10 shared pool

Sound Villas 1454 Wake up to sweeping ocean views in this beautiful Sea Pines retreat, an inviting 4-bedroom, 4-bathroom home perfectly designed for relaxing coastal getaways. With direct beach access, you can spend your days strolling the shoreline, soaking up the sun, or watching dolphins play in the waves. Inside, the home features an open, airy layout with plenty of natural light and comfortable spaces to unwind. The full kitchen is equipped with everything you need for effortless vacation cooking, and the adjacent dining and living areas make gathering together easy.

Check rates on Whimstay →

No. 249

Lagoon front, 3 story condo w balcony & washer dryer, snowbird-friendly

Condo

3 bedroom sleeps 10 private pool

Seascape Villas 3207 Experience the best of Hilton Head Island from this 3 story charming condo just 0.7 miles from Coligny Beach Park. With a prime location near popular attractions like The Boardroom and Harbour Town Golf Links, you'll have endless entertainment options at your fingertips. This condo offers a comfortable retreat with a range of amenities to make your stay enjoyable. Relax by the pool, unwind on the deck or balcony with patio furniture, or head to the beach with easy beach access. Inside, you'll find a well-equipped kitchen with modern appliances, cozy living spaces with TV and cable, and comfortable sleeping arrangements with king, queen, and twin beds.

Check rates on Whimstay →

No. 250

Oceanfront Villa with Shared Pool, Hot Tub, Ocean Views, and More - Beach Nearby

Condo

3 bedroom sleeps 8 shared pool

Island Club 5501 This fifth-floor, oceanfront Island Club villa is a prime getaway for your next seaside vacation. Each guest has access to the complex’s many recreational facilities, including the shared pool/hot tub complex with areas for adults and children, seven clay and two Har-Tru tennis courts, a fitness center, beachside playground, and fishing lagoon. You have easy access to the beach and can access the complex’s amenities via the manicured walkways that wind through the lush tropical vegetation. The restaurants and cafés of Hilton Head are a short drive away from this condo's location in Folly Field.

Check rates on Whimstay →

No. 251

Oceanfront Condo with Ocean View, Shared Pool Hot Tub, and Nearby Beach Access

Condo

3 bedroom sleeps 8 shared pool

Island Club 5201 Recent upgrades, ocean views, and plush new carpets make this oceanfront Island Club condo a welcoming getaway for guests. The complex offers something fun for everyone, with multiple shared pools and hot tub, tanning shelves, a barbecue area, fishing lagoon, and sports courts. Recent upgrades and ocean views make this oceanfront Island Club condo a welcoming getaway for guests. This fantastic retreat features an open kitchen with granite countertops and stainless-steel appliances, so hosting family dinners or preparing picnics to bring to the sand will be a breeze.

Check rates on Whimstay →

No. 252

Oceanfront condo with pools, hot tubs, WiFi, washer, dryer, & central AC

Condo

3 bedroom sleeps 10 private pool

Seacrest 1101 Welcome to SeaCrest Villa 1101! The SeaCrest Villas is an oceanfront resort located in the perfect location on Hilton Head Island, directly across the street from Coligny Plaza. Conveniently located on the first floor and just steps from the front entrance, this villa makes coming and going a snap. The villa is also a short walk to the pools and the beach. The open and comfortable living and dining area with its 10-person table will accommodate your entire group. Share sunsets and happy hours out on the two balconies offering lagoon and distant ocean views.

Check rates on Whimstay →

No. 253

Beachfront getaway with WiFi, pools, hot tub, gym, washer dryer, & central AC

Villa

3 bedroom sleeps 9 private pool

Island Club 5101 Heed the call of the beach at this ground-floor, oceanfront condo in the peaceful, 27-acre Island Club of Hilton Head! Outside, your furnished patio is perfect for morning coffee - courtesy of the Keurig and provided K-cups - or evening cocktails, courtesy of the wet bar just inside. Elsewhere in your open, comfortably furnished condo you'll find a well-equipped, full kitchen ready for any task from making a quiche to pouring a bowl of cereal - you're on vacation, after all. Dine together at the table for eight or keep it casual and pull up a barstool. In the evening, settle down on the cheerful, striped sofas and watch a little TV before bed.

Check rates on Whimstay →

No. 254

Oceanfront Villa with Ocean Views, Shared Pool Hot Tub, and Nearby Beach Access

Condo

3 bedroom sleeps 8 shared pool

Island Club 5204 With panoramic ocean views and an oceanfront location, this newly renovated, three-bedroom, three-bathroom villa will take your breath away! Offering access to multiple shared pools and hot tub, the nearby beach, and much more, your stay at Island Club is sure to be memorable. Those who wish to tour the shops and restaurants of Hilton Head will find them just a short drive away. Island Club's manicured walkways through lush vegetation provide access to the beach and the resort's amenities.

Check rates on Whimstay →

No. 255

Stunning oceanfront villa with WiFi, pool & hot tub, private balcony

Condo

3 bedroom sleeps 7 shared pool

Windsor Court South 3108 3108 Windsor is a stunning 3 bedroom, 3 bath oceanfront villa located in Palmetto Dunes Plantation. As you enter the front door, you’re greeted by sweeping views of the Atlantic, as well as the pristine grounds of the Windsor Court South complex complete with a shared pool and hot tub. Wood flooring, coastal décor, and beautiful furnishings span the entire villa. The open living area provides the perfect area for entertaining and relaxing. The dining table comfortably seats 6, and there is a separate breakfast table located off the kitchen that seats 4. The kitchen features granite countertops, stainless steel appliances and a counter-height bar with 3 bar stools.

Check rates on Whimstay →

No. 256

Oceanfront with Views! Pool & Beach on Hilton Head

Condo

3 bedroom sleeps 10 private pool

2 Hilton Head Beach Villa, Oceanfront three-bedroom and three-bathroom split-level villa in prime South Forest Beach. Experience comfort and convenience at this oceanfront complex featuring state-of-the-art pool facilities opening in May 2024. Just a short walk to Coligny Plaza restaurants and shops and te new Celebration Park! Enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. Experience the ultimate luxury in this stunning split-level, 3-bedroom oceanfront villa that boasts breathtaking views of the sea and easy access to the beach.

Check rates on Whimstay →

No. 257

Oceanfront Villa! Private Beach, Pool, Hilton Head

Condo

3 bedroom sleeps 9 private pool

22 Hilton Head Beach Villa, Three bedroom and three bathroom split-level villa in prime South Forest Beach. Enjoy comfort and convenience at this oceanside complex with state-of-the-art pool facilities. Short walk to Coligny Plaza restaurants and shops and Celebration Park! Enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. Welcome to 22 Hilton Head Beach Villa, located in prime South Forest Beach in the gated Hilton Head Beach Villa complex with state-of-the-art pool facilities. Oceanfront complex with private beach access on site! This split-level villa is divided into four areas.

Check rates on Whimstay →

No. 258

Beachfront escape with pools, hot tub, athletic courts, WD, and central AC

Condo

3 bedroom sleeps 10 private pool

Island Club 5404 Take a break at the beach at this oceanfront condo in the peaceful, 27-acre Island Club of Hilton Head! Outside, enjoy the fresh ocean air and plenty of sunshine from your furnished patio, while inside, you'll find a well-equipped, full kitchen ready to help you prepare everything from your morning coffee to full-course dinners. Dine together or bring a few board games to the dining table, and then settle into the sunlit living area with a TV and plenty of comfortable seating.

Check rates on Whimstay →

No. 259

Sunlit Oceanfront Condo with Two Balconies, Wet Bar, Beach Views & WiFi

Condo

3 bedroom sleeps 6 shared pool

Windsor II 2419 When you're looking to get away for fun in the sun, this Windsor II condo is the place to stay! Its location is so close to the beach that you'll be able to see the waves from the villa's private balconies. To add to the fun, there are two shared pools and a hot tub here. Gardens, fountains, and lagoons add to the appeal of this oceanfront condo complex in the Palmetto Dunes area of Hilton Head Island, SC. A short walk on the resort's boardwalk will lead you to the beach, and there is an outdoor shower for rinsing off the sand after your beach time.

Check rates on Whimstay →

No. 260

Serene Oceanfront Villa with WiFi, Pool, Hot Tub, & Fitness Center

Condo

3 bedroom sleeps 7 private pool

Island Club 2201 Gorgeous ocean views along with a sparkling pool complex and multiple tennis courts are among the many perks of this renovated, oceanfront Island Club condo. While the local vegetation surrounding the Island Club resort makes it feel secluded, you are only a quick walk away from the sandy beaches of the Atlantic Ocean as well as a multi-pool complex, hot tub, fitness center, and nine tennis courts via the resort's manicured walkways. A short drive out of the resort brings you to the shops and restaurants of Hilton Head.

Check rates on Whimstay →

No. 261

Luxury Direct Oceanfront 3BR Panoramic Ocean Views

Villa

3 bedroom sleeps 10 private pool

Island Club 5401 Luxury Oceanfront Retreat. Panoramic Views from Every Bedroom Experience coastal luxury at its finest in this completely renovated 3-bedroom, 3-bath oceanfront condominium. Perfectly situated on the 4th floor, this premier beachfront retreat offers breathtaking panoramic ocean views, direct beachfront access, and upscale finishes throughout. From the moment you enter, you'll be captivated by the stunning ocean vistas visible from the living area dining, kitchen and all three bedrooms. Every detail has been thoughtfully redesigned, featuring brand-new furnishings, designer finishes, custom plantation shutters, and a bright, sophisticated coastal aesthetic.

Check rates on Whimstay →

No. 262

Beachfront villa near golf with pool, hot tub, & balcony - snowbird-friendly

Villa

2 bedroom sleeps 6 private pool

Spa on Port Royal Sound 1123 Boasting a convenient location on Hilton Head Island, as well as many amenities you're sure to appreciate, make this charming villa your next vacation retreat! This beachfront home is a veritable haven for golfing enthusiasts, so be sure to bring your clubs and try your hand at the numerous courses nearby. For even more mellow days, a short drive will take you to beaches for comfy lounging and parks for scenic strolls. The island also sports a number of museums for guests who want to sate their intellectual curiosity and local restaurants for those who are hungrier in a traditional sense.

Check rates on Whimstay →

No. 263

3rd Floor Condo with pools, tennis/pickleball courts, access to beach

Condo

2 bedroom sleeps 4 private pool

Spa On Port Royal Sound 1322 Welcome to your serene getaway in Hilton Head Island! This recently renovated condo is the perfect family-friendly retreat, nestled in a tranquil beachfront community. Located on the 3rd floor, it offers stunning views of the lagoon and fountains that gracefully lead out to the Atlantic Ocean. With two spacious bedrooms and two full bathrooms, this cozy haven is designed for comfort and relaxation. The condo is equipped with all essential amenities, including a well-stocked kitchen, Wi-Fi, and a washer/dryer for your convenience.

Check rates on Whimstay →

No. 264

Perfectly Located Family Condo with Shared Pool, Central AC, Private Washer and dryer, Free WiFi

Condo

2 bedroom sleeps 6 shared pool

Devonshire 207 Devonshire 207 is a beautifully decorated two-bedroom, two-bath, second-floor villa ideally located on the lagoon and golf course in the quaint complex of Devonshire at Port Royal Village. Enjoy the spacious balconies and the lovely Low Country view. This villa has new upgrades and it is a great place to enjoy with your family and friends. Bedroom and Bathroom Configurations: The main bedroom features a wall-mounted flatscreen TV, balcony access, and a private en-suite bath that has a tub/shower combo. The guest bedroom has a wall-mounted flatscreen TV and access to both the covered balcony and the hall bathroom that features a tub/shower combo.

Check rates on Whimstay →

No. 265

Oceanview 4th Floor. 2BR Beach & Tennis Villa

Condo

2 bedroom sleeps 6 private pool

"Discover resort living in this bright 2BR villa. Located in the coveted Admiral's Row building, you are positioned for stunning sunrises and easy beach access. The resort features 10 lighted tennis courts, a fitness center, and multiple on-site restaurants. Whether you’re lounging by the beachfront pool or biking the island’s 50+ miles of trails, this 4th-floor retreat provides comfort and convenience for up to six guests. Need to Know Notes Admiral's Row Sprinkler Project Anticipated Start date: 1/15/2026 Potential Construction Traffic and Noise There will be additional dumpsters and debris on property at this time.

Check rates on Whimstay →

No. 266

Pet-Friendly Inverness Villa on Golf Course

Condo

2 bedroom sleeps 6 shared pool

Discover 987 Inverness Village Villas in Palmetto Dunes, a charming 2-bedroom, 2-bath villa with golf course views, private deck, and peaceful setting. The complex includes a community pool, children’s pool, and tennis courts. A short ride via the Dunes Buggy Shuttle or bike gets you to the beach. Enjoy a vacation reimagined with the property manager, your trusted Hilton Head Island Property Management partner. Discover the charm of Hilton Head Island at 987 Inverness Village Villas, a peaceful retreat tucked within the lush greens of the George Fazio Golf Course in Palmetto Dunes. This inviting villa captures the essence of coastal serenity while offering all the comforts of home!

Check rates on Whimstay →

No. 267

2BR Queen's Grant Villa in Palmetto Dunes, Modern Furnishings, Prime Location, Community Pool!

Villa

2 bedroom sleeps 7 shared pool

763 Queens Grant is a beautifully styled, laid-back pet friendly villa tucked inside the gated community of Palmetto Dunes, where the days are easy, the evenings are even easier, and coming home after a long day at the beach feels like the best part of the whole trip. From the moment you walk through the door, the soaring vaulted ceiling with exposed beams sets the tone, this isn't your average vacation rental. The open living and dining space is generous, airy, and made for togetherness, with a large sectional sofa that the whole group will be fighting over by day two.

Check rates on Whimstay →

No. 268

Condo near beach with 2 pools, restaurants, gym, 6 tennis, 12 pickleball, W D

Condo

2 bedroom sleeps 6 private pool

HH Beach & Tennis B8 Find a true escape in the luxe comfort of this beautiful resort condo that has been recently renovated (2024) to provide you with the ultimate vacation experience! This snowbird-friendly home away from home is part of the renowned Hilton Head Island Beach & Tennis Resort and offers outstanding on-site amenities, including two swimming pools (the largest oceanfront pool on HHI), three restaurants (including a beachfront pool bar), bike rentals (there are 150 miles of bike trails on HH), a fitness center, picnic areas with grilling stations, a playground, a basketball court, a pond with catch-and-release fishing, six tennis courts, 12 pickleball courts, laundry...

Check rates on Whimstay →

No. 269

Pet Friendly Villa with Patio, Pool, + Nearby Golf

Condo

2 bedroom sleeps 5 shared pool

Relax in style at 732 Queens Grant in Palmetto Dunes, a beautifully updated, pet-friendly 2-bedroom, 1-bath villa just minutes from the beach. The spacious open great room features vaulted ceilings and a fully equipped kitchen with island seating. Step outdoors to your private fenced patio with seating and grill. Community pool and convenient beach access make this a perfect coastal escape. Enjoy a vacation reimagined with the property manager, your trusted Hilton Head Island Property Management partner. Welcome to 732 Queens Grant, a charming and thoughtfully renovated villa in the prestigious Palmetto Dunes.

Check rates on Whimstay →

No. 270

Open and Airy 3 Bed 2 Bath St Andrews Villa

Condo

2 bedroom sleeps 6 private pool

St Andrews Common 1780 SEnjoy all the amenities of Palmetto Dunes Ocean Front Resort and Shelter Cove Harbour and Marina when you book a stay at 1780 St. Andrews Common Situated just inside the entrance to the Palmetto Dunes Ocean Front Resort, a picturesque lane leads to the popular St. Andrews complex and this cheerfully decorated second-floor, 2-bedroom, 2-bath villa. Just steps from your private entrance is the St. Andrews pool area (open April through September) complete with plenty of seating, shade, sun, and views of the nearby lagoon and wildlife.

Check rates on Whimstay →

No. 271

Oceanfront condo with WiFi, pool, hot tub & beach access

Condo

2 bedroom sleeps 5 private pool

Island Club 6501 With exquisite ocean views from your private balcony, extra seating in the living room area, and updated bathrooms, this Island Club rental is the perfect destination for your next beach vacation. The Island Club complex is close to the center of activity on Hilton Head Island. This property is surrounded by lush, sub-tropical vegetation, making it feel peaceful and secluded. Walking paths along manicured lawns allow you to access the private beach and the resort's amenities, including picnic and barbecue plots, three pools, a shared hot tub, nine tennis courts, a fitness center, and a fishing lagoon.

Check rates on Whimstay →

No. 272

Spacious Patio and Community Pool - Elegant Coastal Hideaway

Condo

2 bedroom sleeps 6 shared pool

HOST & HOME presents… 592 Queen's Grant! Situated in the heart of Queen's Grant Community of renown Palmetto Dunes, this hideaway for up to 6 guests boasts a large outdoor patio and steps from the community pool to become your perfect escape. Just.5 away from sandy beaches, you'll be close enough to everything the island has to offer: from fine dining and marine adventures, to golf and racquet clubs next door. Learn more below… HIGHLIGHTS Spacious Villa: Accommodates up to 6 guests with 2 bedrooms and 2 bathrooms. Outdoor Oasis: Spacious patio and a grill for evening BBQs Resort Amenities: Access to golf, tennis, a community pool, bike trails, and nearby beaches just.5 miles away!

Check rates on Whimstay →

No. 273

Beachfront Getaway. Pool, Tennis + Ocean Air

Condo

2 bedroom sleeps 5 private pool

Just steps from the beach in Folly Field, 436 Hilton Head Beach and Tennis is a renovated 2BR/2BA condo featuring a modern kitchen, balcony with ocean peek views, flexible sleeping options, and resort amenities like oceanfront pools, tennis courts, lagoon, tiki bar, and more. Enjoy a vacation reimagined with the property manager, your trusted Hilton Head Island Property Management partner. Important Community Notice - Active Construction at Admirals Row Please be advised that Admirals Row Buildings A and B will begin an 18 month active sprinkler system repair project on February 2.

Check rates on Whimstay →

No. 274

Coastal Escape w/ Pool & Ocean Peek!

Condo

2 bedroom sleeps 6 shared pool

Discover 241 Hilton Head Beach and Tennis, an updated 2-bedroom, 2-bath villa in the Admirals Row section of Hilton Head Beach and Tennis. Relax in the airy living space, prepare meals in the modern kitchen, and step out to the second-floor balcony with views toward the pool and ocean. Enjoy resort amenities like a communal pool, tennis & pickleball courts, beachfront access, and an on-site restaurant. Enjoy a vacation reimagined with the property manager, your trusted Hilton Head Island Property Important Community Notice - Active Construction at Admirals Row Please be advised that Admirals Row Buildings A and B will begin an 18 month active sprinkler system repair project on February 2.

Check rates on Whimstay →

No. 275

Fully Equipped Kitchen and Resort Amenities Await - Spacious Villa Retreat

Condo

2 bedroom sleeps 6 private pool

This spacious two bedroom two bath villa is located on the second floor of Admirals Row B building. The master bedroom is furnished with a king size bed. The second bedroom is furnished with two twin size beds. For additional sleeping there is a sleeper sofa located in the living room. The kitchen comes fully equipped. Enjoy your morning coffee from your furnished balcony or enjoy a short walk to the beach, pool, tennis courts, or playground.

Check rates on Whimstay →

No. 276

Beachfront condo w pool, tennis and pickleball, gym & balcony

Condo

2 bedroom sleeps 6 private pool

HH Beach & Tennis 322AR Need to Know Notes Admiral's Row Sprinkler Project Anticipated Start date: 1/15/2026 Potential Construction Traffic and Noise There will be additional dumpsters and debris on property at this time. Timeline: Up to 18 months This project will begin at Admiral's Row Building B, which could impact guests staying in Admiral's Row Building A and Ocean View Building A. Experience the ultimate beachfront getaway at this 3rd floor, light, and bright condo located within the prestigious Hilton Head Beach & Tennis Resort. Just steps away from direct boardwalk access to the beach, this condo offers stunning ocean views and a prime location for enjoying the sun, sand, and surf.

Check rates on Whimstay →

No. 277

Scenic Balcony and Resort Amenities - Charming Villa Retreat

Condo

2 bedroom sleeps 6 private pool

This lovely two bedroom two bath villa is located on the second floor in Admirals Row building B. The master bedroom is furnished with a queen size bed. The guest bedroom is furnished with a set of twin beds. For additional sleeping there is a queen sleeper sofa in the living room. The kitchen comes fully equipped. Enjoy the beautiful view from your furnished balcony or enjoy a short walk to the beach, pool, tennis courts or playground.

Check rates on Whimstay →

No. 278

Oceanfront, 3rd floor villa with corner balcony, pool and beach access

Villa

2 bedroom sleeps 6 private pool

Sea Cloisters 311 Immerse yourself in the soft blues of the ocean both inside and out at this oceanfront condo in the Sea Cloisters. Wake up each morning to a panoramic view of the Atlantic, sit down for breakfast on your breezy corner balcony, and spend the day swimming, surfing, and beachcombing downstairs. The Sea Cloisters is an oceanfront property that sits directly adjacent to Folly Field Beach Park on the scenic shores of Hilton Head Island. Its 25 acres include a beachfront swimming pool, a kiddie pool, a grilling area, bike paths, and direct access to the sandy beach.

Check rates on Whimstay →

No. 279

Calming Condo Getaway with Shared Pool, Hot Tub, and Tennis Courts

Condo

2 bedroom sleeps 7 shared pool

Island Club 3105 Walk to the beach, relax in the pool and hot tub, or play some tennis with your friends at this beautiful villa on the beach in Hilton Head! With beautiful landscaping and incredible amenities, including a easy beach access, this condo is the perfect destination for an oceanfront getaway. Located just a short drive from the many shops and restaurants of Hilton Head Island, this condo makes it easy to explore all the island has to offer. If you'd rather stay on the property, you'll find plenty there to enjoy, from an on-site pool to a well-equipped fitness center, as well as nine tennis courts and a shared jacuzzi.

Check rates on Whimstay →

No. 280

Newly renovated beachfront condo with pool, tennis, restaurants, gym, & balcony

Condo

2 bedroom sleeps 6 private pool

HH Beach & Tennis 415AR Need to Know Notes Admiral's Row Sprinkler Project Anticipated Start date: 1/15/2026 Potential Construction Traffic and Noise There will be additional dumpsters and debris on property at this time. Timeline: Up to 18 months This project will begin at Admiral's Row Building B, which could impact guests staying in Admiral's Row Building A and Ocean View Building A. Experience the ultimate beachfront getaway at this newly renovated, light, and bright condo located on the fourth floor of the Admirals Row Building within the prestigious Hilton Head Beach & Tennis Resort.

Check rates on Whimstay →

No. 281

Tennis Villas B04

Condo

2 bedroom sleeps 6 private pool

"Walk through the door of this villa and enter a tropical retreat. Tastefully decorated in palm trees, beach scenes and lighthouses, you will immediately know that you are a million miles from your everyday life. A queen-size bed, two twin beds. new living area queen sleep sofa and 2 new chairs. comfortably accommodate up to 6 people. Two full size bathrooms and full-size kitchen provide all you need. Updated cabinets, over the stove microwave oven, new counter top and new dishwasher we added just few years ago. A rich ceramic floor leads you throughout the villa.

Check rates on Whimstay →

No. 282

Tennis Villas F09

Condo

2 bedroom sleeps 6 private pool

Two-Bedroom - Tennis Villa - Resort View - Villa F bldg. You are sure to have all the comforts of home from the fully equipped kitchen to the furnished balcony with great views of the tennis courts. The master bedroom is furnished with a king size bed. The second bedroom has two twin size beds. If additional space is needed a sleeper sofa is in the living area. Tennis Villas F9 Professionally Managed by HHIB&T Vacation Rentals STR Permit #077894 HHIB&T Vacation Rentals is the largest and ONLY full service on-site vacation rental company operating at Beach and Tennis, thereby offering the greatest selection of villas to fit even the most discriminating taste.

Check rates on Whimstay →

No. 283

Coastal Views and Direct Beach Access - Stunning Beachfront Retreat

Condo

2 bedroom sleeps 6 private pool

Wake up to the sound of waves and partial ocean views at this beachfront villa in the heart of South Forest Beach. With direct access to the sand via a scenic private boardwalk, this first-floor retreat puts you within walking distance of Coligny Plaza, Lowcountry Celebration Park, and all the shops and restaurants South Forest Beach has to offer. Whether you're planning a family vacation or a relaxing island escape, this home creates the perfect setting for unforgettable Hilton Head memories. Sliding glass windows flood the living space with natural light, offering uninterrupted views of the natural landscape beyond.

Check rates on Whimstay →

No. 284

Gorgeous Oceanfront Villa, w/ Pool on Hilton Head

Condo

2 bedroom sleeps 6 private pool

21 Ocean Club, This beautiful villa has 2 bedrooms and 2 bathrooms, which have been recently renovated. The main floor has a living room, dining area, kitchen, and laundry room, while the bedrooms are upstairs. The villa is located less than a minute away from the beach and has a pool nearby. Parking is available right in front of the villa. The Ocean Club Complex is oceanfront and has a private path leading to the beach. You can now enjoy a reimagined vacation with the help of the property manager, Welcome to 21 Ocean Club, where the waves serenade, and the sunsets paint the sky in hues of magic!

Check rates on Whimstay →

No. 285

Dreamy condo on the beach with balcony view, shared pool, & charming decor

Condo

2 bedroom sleeps 6 shared pool

Hampton Place 6407 Put your feet up and relax under an umbrella on the pristine sand of Hilton Head Island when you make this condo your home-away-from-home! From the bright floor-to-ceiling windows to the open layout, each guest will find their own favorite space to spread out. The efficient floorplan of the kitchen will make for quick mealtimes and making a delicious meal a breeze, so let the chef of the group show off their skills. Step out to the furnished balcony with a glass of wine in the evening and soak up the island lifestyle before heading in for a movie night on the flatscreen TV.

Check rates on Whimstay →

No. 286

Oceanfront villa with WiFi, full kitchen, pool, & hot tub - beach nearby

Condo

2 bedroom sleeps 6 private pool

Island Club 1203 This lovely Island Club villa features upscale renovations for ultimate comfort, plus access to a shared hot tub, pool, and beach access nearby. Featuring all new flooring and fresh paint, this renovated condo is perfect for your next family getaway. Easily enjoy swimming, athletic activities, and a variety of games for a memorable vacation. While spending time at this resort, enjoy the ocean breeze from the shared deck overlooking the beach. Make use of all the community features found on the property, including shared tennis courts, basketball courts, lawn games, a children's playground, pickleball courts, fitness center, and more!

Check rates on Whimstay →

No. 287

Oceanfront Condo with Shared Pool, Hot Tub, Beach Access & Playground

Condo

2 bedroom sleeps 6 shared pool

Island Club 1101 Kick back and relax in the charming comforts of this two-bedroom condo with peekaboo views of the beach in Hilton Head. The condo is decorated to inspire comfort and relaxation, but when you are ready to venture out for a day of fun, everything you need is located on-site. From a shared lap pool, hot tub, and kiddie splash pool to sports courts, a sun deck, and a barbecue area with grills and tables, you will have access to the full range of amenities at the Island Club.

Check rates on Whimstay →

No. 288

Amazing oceanfront 2BR 2BA 1st floor condo with pool, hot tub, tennis, fitness area, & WD

Condo

2 bedroom sleeps 7 private pool

"Island Club 4104 Experience the extraordinary when you stay at this vacation rental in gorgeous Hilton Head Island. Upon entry into this completely remodeled condo, you'll be met with a bright interior and a cozy atmosphere throughout the well-appointed living space. Relax and make yourself at home by resting on the brand-new plush furniture, streaming your favorite movies on the large TV, or serving brunch on the patio while enjoying the refreshing sea breeze. Hobby chefs will love preparing grand meals and beach picnic snacks in the full kitchen featuring brand-new, high-quality appliances, including a new refrigerator, along with other significant kitchen upgrades completed this spring.

Check rates on Whimstay →

No. 289

Peaceful Oceanfront Villa with Pools, Hot Tub, Tennis, & Ocean View

Condo

2 bedroom sleeps 7 private pool

Island Club 1304 Experience a pleasant stay dipping in and out of the pool, playing tennis, or working out at the on-site fitness center when you stay at this oceanfront Hilton Head condo! In the evening, relax with a glass of wine on the villa’s private balcony facing the ocean. This third-floor, two-bedroom Island Club villa overlooks the resort's beautifully landscaped grounds and is within walking distance to the beach. The nearby shops, restaurants, and art galleries also offer a full day of activities.

Check rates on Whimstay →

No. 290

2BR Beach Villa with Balcony Pool Tennis Access

Apartment

2 bedroom sleeps 5 private pool

Escape to paradise at our 2-bedroom apartment in the heart of Hilton Head Island! Just steps from the beach, enjoy sun, sand, and surf. The apartment features a private balcony for relaxing views, plus access to a swimming pool and nearby tennis courts. Perfect for families, couples, or small groups seeking a comfortable and convenient coastal getaway. This 2-bedroom, 2-bath villa is located on the second floor of the Tennis Villas and is a great spot for a relaxing Hilton Head Island getaway. With a comfortable layout, private balcony, and easy access to the beach and resort amenities, it’s a convenient and inviting place to stay.

Check rates on Whimstay →

No. 291

Oceanfront condo with a washer, dryer, central AC, pool, hot tub & beach access

Condo

2 bedroom sleeps 6 shared pool

Shorewood 311 At this Hilton Head condo, you can take a dip in the seasonally-heated, shared pool, walk on the sand and splash in the ocean, or soak your cares away in the soothing hot tub - whichever you chose, relaxation is close-at-hand! This sunny and bright condo comes with a well-equipped, full kitchen with stainless steel appliances and a breakfast bar, a dining table for mealtimes or rainy day board games, and a sun-kissed living area with matching sofas and a TV for evening channel surfing. Outside, savor your morning coffee or dine alfresco on your furnished balcony while taking in the amazing beach and ocean view.

Check rates on Whimstay →

No. 292

A Quiet Beach Getaway with Pools, Hot Tub, Tennis Courts, and Private Patio

Condo

2 bedroom sleeps 5 private pool

Island Club 3106 With walk-out beach access, two patios, and nine tennis courts, this Island Club villa is just right for your family. Unlimited use of the club's amenities comes with your stay, making it easy to ensure you and your loved ones are never bored! Your condo in Folly Field is surrounded by well-manicured foliage and vegetation for maximum solitude, yet still keeps you close to the beach and the club's numerous amenities. Take a dip in the pool, play an invigorating game of tennis, or relax with a soak in the hot tub.

Check rates on Whimstay →

No. 293

First Floor, Oceanfront Condo with Free WiFi, Balcony, Shared Hot Tub, Pool, Sauna

House

2 bedroom sleeps 8 private pool

Villamare 1103 This coastal-themed and newly renovated condo in Palmetto Dunes offers amazing ocean and pool views! The first-floor location will make this condo accessible for everyone! Gain access to the balconies from both bedrooms, as well as the living room. This open floor plan allows for breathtaking views from every room. The living room features a flatscreen TV with a queen sleeper sofa. The main bedroom features a king with a private bathroom with a beautiful walk-in shower and flatscreen TV. The guest bedroom has two queens with coastal chic furniture, an updated walk-in shower, and flatscreen TV.

Check rates on Whimstay →

No. 294

A Relaxing Getaway with Shared Pools and Hot Tub in an Oceanfront Villa

Condo

2 bedroom sleeps 4 shared pool

Island Club 5302 This two-bedroom, two-bathroom condo on the third floor of the Island Club is an ideal getaway destination. Gorgeous views abound whether you're on the private balcony or your own personal spot on the beach. Hop in the car for the short drive from the villa to Hilton Head's spas, shops, and eateries, or walk less than a mile to the sandy beach. Follow the walkways to the private beach and sundeck, or check out the family-friendly pools, hot tub, tennis courts, basketball court, fishing lagoon, fitness center, playground, and picnic areas. Large sliding doors open onto the balcony and offer an expansive view of the ocean from the kitchen, dining area, and living room.

Check rates on Whimstay →

No. 295

Admiral's Row 130

Condo

2 bedroom sleeps 6 private pool

This beautiful two-bedroom, two-bathroom villa is located on the first floor. There is a full size fully equipped kitchen, dining area, living area with sleeper sofa. The master bedroom has a king size bed. The guest bedroom has two twin size beds. Enjoy the salt air and view right from the furnished balcony or take a short walk to the beach, pools or courts! Resort View - Admiral's Row 130 Professionally Managed by HHIB&T Vacation Rentals HHIB&T Vacation Rentals is the largest and ONLY full service on-site vacation rental company operating at Beach and Tennis, thereby offering the greatest selection of villas to fit even the most discriminating taste.

Check rates on Whimstay →

No. 296

Splendid condo, pool, full kitchen, & patio

Condo

2 bedroom sleeps 6 private pool

Greens 153 Nestled within the exclusive Shipyard Plantation in Hilton Head, SC, The Greens condominiums offer a serene retreat for your vacation getaway. Just a short two and a half blocks from the Atlantic Ocean, the Sonesta Oceanfront resort, and the Van der Meer Tennis Academy, this condo provides the perfect location for beach lovers and sports enthusiasts alike. Step inside this spacious condo to discover a beautifully upgraded kitchen featuring granite countertops and stainless steel appliances, perfect for preparing meals during your stay. The open layout creates a welcoming atmosphere, ideal for relaxing after a day of exploring all that Hilton Head has to offer.

Check rates on Whimstay →

No. 297

Spacious updated oceanfront condo with shared pools, hot tub & beach access

Condo

2 bedroom sleeps 8 shared pool

Windsor Place 207 Spacious 2nd floor, corner villa is perfect for families, couples, and friends traveling together because of the floor plan, 1442 square feet, featuring tall ceilings and amazing ocean views from the living areas and both bedrooms. Take in the views of the lush gardens with fountains, pools, hot tubs, and the Atlantic Ocean beyond. This expansive condo has a well-appointed kitchen with grilling tools, stainless steel appliances, granite countertops and is open to the dining area and large great room. The dining table seats 6 people normally and 10 with use of easy built-in butterfly leaf, plus 2 bar stools. Just off of the kitchen is a closet containing a washer and dryer.

Check rates on Whimstay →

No. 298

Luxury Villa Rooftop Pool near Beach Hilton Head

Condo

2 bedroom sleeps 6 private pool

Stunning Hilton Head villa with 2 bedrooms, 2 baths, and newly renovated interiors. Enjoy the perfect seaside getaway steps from the beach and Coligny Plaza. Relax by the rooftop pool or explore the charming Forest Beach area. Book your coastal retreat today! If you're looking for a cozy seaside getaway, look no further than this beautiful villa in North Shore Place Hilton Head. With two bedrooms and two bathrooms, this place has been renovated to perfection with new furnishings, a modern kitchen, and a brand-new walk-in shower. It's the perfect place to unwind and enjoy the beauty of the beach.

Check rates on Whimstay →

No. 299

Beachfront escape with pools, hot tub, WiFi, washer dryer, & central AC

Villa

2 bedroom sleeps 8 private pool

Island Club 2103 Escape to the beach at this beautifully situated ground-floor, oceanfront condo in the peaceful, 27-acre Island Club on Hilton Head Island. Perfect for a relaxing coastal getaway, this charming retreat offers the ideal blend of comfort, convenience, and resort-style amenities. Step outside to your private furnished patio, where you can enjoy the fresh ocean breeze, listen to the waves, and soak up the beautiful South Carolina sunshine. Inside, you’ll find a bright and welcoming living space designed for relaxation. The well-equipped full kitchen has everything you need to prepare anything from your morning coffee to delicious home-cooked meals after a day at the beach.

Check rates on Whimstay →

No. 300

Ocean view condo at beachfront resort with pool, hot tub, pickleball & tennis

Condo

2 bedroom sleeps 6 private pool

Island Club 4403 Elegantly furnished and beautifully situated within sight of the Atlantic Ocean, this Island Club condo is Hilton Head living as you want it to be. It's a place to spend your days walking down to the beach, playing tennis and pickleball, and unwinding in the seasonal swimming pool and hot tub. The Island Club is a beachfront resort community, with a host of wonderful amenities across its 27-acre grounds.

Check rates on Whimstay →

No. 301

Oceanfront Villa with Shared Pools, Hot tub, and Beach Access

Condo

2 bedroom sleeps 8 shared pool

Villamare 1407 Oceanfront villa just remodeled, steps from the beach, sizable pool, and hot tub! Pristine, comfy condo lets you go to sleep to the sound of the waves. Scenic ocean views from every room and balcony. This oceanfront villa has two sides accessible through separate doors. The A side includes fully equipped kitchen, living room with flatscreen TV and queen-size sleeper sofa, and a master bedroom with a king-size bed. Flatscreen, vanity, and private bathroom with tiled, walk-in shower. The B side of the villa includes a guest bedroom with two full-size beds and a private bathroom with walk-in shower. Free Wi-Fi and cable TV.

Check rates on Whimstay →

No. 302

Newly-renovated ocean front condo on the 5th floor with a private balcony

Condo

2 bedroom sleeps 8 private pool

Shorewood 511 Welcome to Shorewood 511, an amazing oceanfront condo that has been completely renovated, restocked, and redecorated for 2023 to include all new TV, furnishings, mattresses, and inventory. Some of the closest attractions are the island’s very best! Nearby Coligny Plaza is a great place for dining, shopping, and entertainment. The kids will have fun playing in the fountain at Coligny Beach Park! Rent bikes and ride the miles of bike paths, or you may want to just rent an umbrella and chair from the lifeguard and relax with a book on the beach!

Check rates on Whimstay →

No. 303

Cozy oceanfront villa, tennis courts, hot tub, shared pool and ocean view

Condo

2 bedroom sleeps 6 shared pool

Island Club 5402 This newly renovated oceanfront villa provides gorgeous ocean views from the entryway through to the living room and onto the private 4th floor balcony where you will enjoy the stunning morning sunrises, beautiful beach views and the sound of the waves hitting the shore. The two-bedroom, two-bathroom villa has been totally renovated to include new custom cabinets, quartz countertops, stainless steel appliances, and a private laundry in a fully equipped kitchen which will certainly enhance your stay. Enjoy the 75” Flatscreen TV with DVD in the living room as well as additional TV’s in the two bedrooms.

Check rates on Whimstay →

No. 304

Oceanfront condo with pools, hot tubs, fitness room, & central AC

Condo

2 bedroom sleeps 6 private pool

Seacrest 2304 Welcome to your dream vacation spot on beautiful Hilton Head Island! Our perfectly-located, oceanfront resort is directly across the street from Coligny Plaza, where you'll discover more than 60 shops and restaurants. Start your day by stepping out onto one of your two private, furnished balconies with stunning ocean views to catch the sunrise before heading downstairs to explore the many on-site amenities or take a leisurely stroll on the warm sands. This property is also ideally situated near numerous local attractions, including the renowned Shipyard Golf Club, just under two miles away.

Check rates on Whimstay →

No. 305

51 Ocean Club

Villa

2 bedroom sleeps 6 private pool

Oceanfront Villa in S.Forest Beach. 2BD/2BA/Hosts 6 Proudly hosted this oceanfront villa in the heart of South Forest Beach offers the ultimate beachfront getaway with unbeatable convenience and coastal charm. Located on the main floor, this beautifully appointed 2-bedroom, 2-bath villa accommodates up to 6 guests and allows you to park right outside your door, unload with ease, and enjoy the comfort of single-level living throughout your stay. Designed with inviting nautical and coastal-inspired décor, the villa immediately sets the tone for a relaxing beach vacation the moment you step inside.

Check rates on Whimstay →

No. 306

Stunning Oceanfront Villa - 3rd Floor Views and Renovated 2026

Apartment

2 bedroom sleeps 5 private pool

Island Club 3302 is a fully renovated oceanfront villa offering sweeping 3rd-floor views, modern luxury finishes, and direct beach access. Designed for comfort and style, this 2BR/2BA retreat combines elevated coastal design with resort amenities, perfect for a relaxing Hilton Head getaway. This Island Club unit provides a brand new, beautifully appointed 2 bedroom, 2 bath oceanfront villa with spectacular sweeping ocean views from its 3rd floor location and so many elevated features that you will easily experience the best of Hilton Head while enjoying the calming rhythm of the ocean.

Check rates on Whimstay →

No. 307

Exquisite oceanfront top-floor condo has the feel of paradise on earth

Condo

2 bedroom sleeps 7 private pool

Island Club 5503 Experience spectacular unobstructed ocean views, morning sunrises, and beautiful beach views from the moment you enter the front door, all the way through the living room to the top floor balcony. Enjoy luxury vinyl flooring throughout, as well as professionally curate coastal décor, new bedding, plantation shutters, and solid doors for added privacy. All-new smart TVs allow you to access your streaming services as well as a broad spectrum of channels provided by free cable and internet services. The recently renovated kitchen includes custom cabinetry, a quartzite countertop, top-of-the-line stainless steel appliances, and a full-size washer/dryer.

Check rates on Whimstay →

No. 308

Oceanfront resort condo with WiFi, balcony, pool, grills, & beach access

Condo

1 bedroom sleeps 4 shared pool

Sea Side Villas II 252 Serenity by the sea awaits at this one-bedroom condo at Sea Side Villas! Centrally located steps from Coligny Beach Park and Plaza, this complex boasts an on-site pool, grill areas, a sun deck, and direct beach access. A new shower house located on the beach path offers a convenient place to rinse off sandy feet and beach gear. Enjoy morning coffee and sunset cocktails from your own private balcony. This breezy one-bedroom condo features coastal decor and all the essentials of home including a full-size kitchen everything you need to whip up some snacks for the beach or a visit to the shared pool.

Check rates on Whimstay →

No. 309

Secluded & Peaceful - Vacation Getaway with WiFi, Pool, Hot Tub, & Private Beach

Condo

1 bedroom sleeps 4 private pool

Island Club 153 With access to a private beach and multiple tennis courts along with a peaceful feeling of seclusion, this one-bedroom condo makes gatherings of family and friends extra special. Surrounded by palmettos, oaks, and other vegetation natural to the Hilton Head environment, this resort feels hidden away while still in the center of activity. In addition to the resort's private beach, multi-pool complex, fishing lagoon, and nine tennis courts, it's less than a half-mile drive or walk to the hot tub at the Hilton Head Westin or a couple miles to restaurants and shopping at The Plaza at Shelter Cove. This first-floor villa with free WiFi is comfortable and spacious.

Check rates on Whimstay →

No. 310

Spacious condo with pool, tennis courts, & golf on-site

Condo

1 bedroom sleeps 4 private pool

Greens 204 The Greens condominiums are within Shipyard Plantation, a private residential and resort community with many biking and walking paths. The complex encompasses two and a half blocks of the Atlantic Ocean, the Sonesta oceanfront resort, and the Van der Meer Tennis Academy. The condo offers a spacious layout, an upgraded kitchen with granite and stainless steel appliances, plus all-new carpets, tile, new wood laminate, furniture, new bathroom vanities, and new drapes. This home is beautiful and has all the comforts you expect including two flat-screen TVs and free WiFi.

Check rates on Whimstay →

No. 311

Seaside 247

Condo

1 bedroom sleeps 4 private pool

Enjoy an affordable beach escape in this oceanfront complex, just steps from the sand! This beautifully updated second-floor villa now features a renovated kitchen (March 2026) with modern finishes and a brand-new standing shower for a fresh, spa-like feel. Unwind in the comfy king bed, enjoy smart TVs in both rooms, and stay connected with WiFi. The fully equipped kitchen makes meals a breeze, whether you're cooking in or enjoying takeout. Relax on your private balcony with a partial ocean view, or take in the pool view from the front door. A budget-friendly option in a prime location, perfect for a relaxing Hilton Head retreat!

Check rates on Whimstay →

No. 312

Hilton Head Beach & Tennis Resort, Oceanfront, Tennis, Restaurants, Pickleball!

Condo

1 bedroom sleeps 4 shared pool

Escape to this inviting condo at Hilton Head Beach & Tennis Resort, where resort-style amenities and coastal charm come together for an easy island getaway. Tucked within the lush, palm-lined grounds of the resort, this retreat puts you just steps from the resort's Community Pool, tennis and pickleball courts, and on-site dining at Coconutz Pizza & Wings and Jamaica Joe'z oceanfront beach bar, making it effortless to fill your days with sun, recreation, and good food without ever leaving the community. Inside, the living area feels warm and welcoming, centered around a cozy stone fireplace and a Smart TV for relaxed evenings after a day at the pool or courts.

Check rates on Whimstay →

No. 313

Seaside 278

Condo

1 bedroom sleeps 4 private pool

Wake up to ocean views from your private balcony in this charming, coastal-themed villa just steps from the beach. Located on the second floor near the front of the building, this bright and breezy space features a comfortable king bed, queen sleeper sofa, and a recently updated shower/tub. The fully equipped kitchen makes dining in easy, and we’ve stocked the villa with beach chairs, bikes, games, and beach toys to make your Hilton Head stay fun and effortless! Seaside is a gated-oceanfront complex in the heart of Hilton Head's main beach, but just far enough that the beach is not overcrowded.

Check rates on Whimstay →

No. 314

Second-floor condo in beachfront complex with pools, tennis & gym

Condo

1 bedroom sleeps 6 private pool

Spa On Port Royal Sound 2217 Find every essential for a fun-filled beach vacation at this updated, second-floor condo at The Spa on Port Royal Sound. As part of this oceanfront complex, you'll enjoy easy access to the beach, wonderful on-site amenities, and the beautiful golf courses and bike paths of Hilton Head Island. This condo faces the courtyard at The Spa on Port Royal Sound, a beachfront property with indoor and outdoor swimming pools, a fitness center, tennis and basketball courts, grilling and picnic areas, a playground, and a gorgeous stretch of beach on Port Royal Sound.

Check rates on Whimstay →

No. 315

Spacious Villa with Balcony and Resort Amenities - Elegant Coastal Haven

Condo

1 bedroom sleeps 6 private pool

This spacious one bedroom, one bath villa is located on the second floor of Ocean Villa B building. The villa has a fully equipped kitchen, dining/living area with a sleeper sofa. The master bedroom is furnished with a queen size bed. There are a set of captain's bunks located in the hallway, perfect for the kids!! Enjoy your morning coffee on the balcony then venture out to the beach, pool and tennis courts that are only steps away!!

Check rates on Whimstay →

No. 316

Spacious Villa with Scenic Balcony and Resort Access - Stylish Coastal Haven

Condo

1 bedroom sleeps 6 private pool

This spacious one bedroom one bath villa is located on the first floor of Ocean Villa C Building. This villa had a fully equipped kitchen, dining/living area with a sleeper sofa. The master bedroom is furnished with a king size bed. There are a set of captain's bunks located in the hallway, perfect for the kids!! Enjoy your morning coffee on the balcony then venture out to the beach, pool, and tennis courts that are only steps away!!

Check rates on Whimstay →

No. 317

Beach-view condo in oceanfront complex with outdoor pool, beach access, balcony

Condo

1 bedroom sleeps 4 shared pool

Breakers 225 On-site beach access and a walkable location? Say less! This no-frills condo in Hilton Head Island is your next South Carolina vacation destination. Located in The Breakers Resort, this second-floor condo provides an easy-as-can-be stay for small beach-loving groups. Take advantage of the dedicated beach access just steps away from the property, as well as nearby shopping, dining, and a community pool. The beauty of Hilton Head Island is at your fingertips when you stay in SC! Inside, discover an air-conditioned home away from home with an inviting open floor plan where you can lounge, relax, and create everlasting memories with your guests!

Check rates on Whimstay →

No. 318

Seaside 358

Condo

1 bedroom sleeps 4 private pool

Fully renovated oceanview villa with all-new finishes and furnishings! Enjoy a comfortable King bed, Queen sleeper sofa, spacious tiled shower, and a fully equipped kitchen with full-size black stainless appliances and stone countertops. Smart TVs in both the living room and bedroom. Beach chairs and two bikes included! Located in Seaside Villas, a gated oceanfront complex just steps to the sand and a short walk to Coligny Plaza, the Tiki Hut, dining, shops, and more. Seaside is a gated-oceanfront complex in the heart of Hilton Head's main beach, but just far enough that the beach is not overcrowded.

Check rates on Whimstay →

No. 319

Panoramic Views and Luxurious Amenities - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 6 private pool

If you’re searching for the perfect oceanfront getaway with breathtaking panoramic views, look no further. From the moment you step inside, you’ll be captivated by endless views of the ocean, ocean, ocean, ocean! Located on the third (top) floor, this beautifully refreshed villa offers ultimate tranquility with no neighbors above you. The unit has been thoughtfully updated with all-new televisions, upgraded kitchen accessories worthy of a master chef, a stylish outdoor patio set, luxury hotel-style showerheads, and premium bedding for a truly relaxing stay. The décor is bright, airy, and coastal-inspired, creating a fresh and welcoming atmosphere throughout.

Check rates on Whimstay →

No. 320

Dont Worry, Beach Happy 1BR Oceanview King Bed Villa in HHBT Resort

Villa

1 bedroom sleeps 4 private pool

HH Beach & Tennis 233C Wake up to breathtaking, unobstructed ocean views in this coastal chic villa at the ever popular Hilton Head Beach & Tennis Resort. Perfect for couples or small families, this newly listed retreat is literally steps to the beach. Start your mornings with coffee on the private balcony as the sun rises over the Atlantic, and unwind in the evenings with a brand new 55” Smart TV, high speed WiFi, and central AC comfort. Step inside to a well equipped kitchen with stainless steel appliances and granite countertops, refresh in a full bathroom with a tub/shower combo, and stretch out in a plush king bed and sleeper sofa.

Check rates on Whimstay →

No. 321

Stunning Views and Resort Amenities - Charming Oceanfront Haven

Condo

1 bedroom sleeps 6 private pool

This lovely one bedroom villa is located Oceanfront in Admiral's Row. The master bedroom is furnished with a Queen size bed. A set of captains bunks are located in the hallway-great for the kids! The living/dining area includes a sleep sofa and fully equipped kitchenette. Enjoy the great views right from the furnished balcony or enjoy a short walk to the beach or pool. Oceanfront - Admiral's Row 106 Professionally Managed by HHIB&T Vacation Rentals HHIB&T Vacation Rentals is the largest and ONLY full service on-site vacation rental company operating at Beach and Tennis, thereby offering the greatest selection of villas to fit even the most discriminating taste.

Check rates on Whimstay →

No. 322

309 Breakers

Villa

1 bedroom sleeps 6

Ocean Views. Walk to Everything! 1BD/1BA/Hosts 5. Free Bikes! Proudly hosted this beautifully remodeled oceanfront villa in the heart of North Forest Beach offers breathtaking Atlantic views, modern coastal style, and an unbeatable walk-everywhere location. Situated in an end-unit at the popular Breakers community, this inviting retreat accommodates up to 5 guests and is the perfect home base for couples, small families, or friends looking to experience the very best of Hilton Head Island. Inside, the bright, open-concept living space is designed to maximize the spectacular ocean views.

Check rates on Whimstay →

No. 323

231 Breakers

Villa

1 bedroom sleeps 5 private pool

Oceanfront Dream Villa in North Forest Beach! Free Bikes and Close to Everything! Proudly hosted this bright and inviting oceanfront villa offers the perfect blend of comfort, convenience, and coastal charm in the heart of North Forest Beach. With beautiful natural light and a relaxed beachy feel throughout, this one-bedroom retreat is designed to make your island getaway effortless from the moment you arrive. The thoughtfully arranged layout includes a comfortable bedroom with a queen bed, a sleeper sofa in the living room, and a cozy twin bed tucked into the hall area, perfect for small families or groups.

Check rates on Whimstay →

No. 324

Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access

Apartment

1 bedroom sleeps 4 private pool

Breakers 324 is a top-floor oceanfront condo on Hilton Head Island, offering breathtaking ocean views of the Atlantic from a private balcony. This bright, inviting unit features a comfortable living area with a sleeper sofa and TV, a well-appointed bedroom with a King Bed and Build in Bunk Beds. 2 suitable for Children, a modern kitchenette for light cooking, and a private in-unit washer and dryer. Located directly on Coligny Beach, guests enjoy easy access to the sand, a heated oceanfront pool, and a peaceful, private atmosphere.

Check rates on Whimstay →

No. 325

Coastal condo on the beach with panoramic views, beach access & a shared pool

Condo

1 bedroom sleeps 2 shared pool

Hampton Place 5501 Offering gorgeous views of the coast from the private balcony, this newly renovated villa is a spacious paradise perfect for a couple’s getaway. Recent upgrades include new kitchen cabinets, beautiful quartz countertops, a complete remodel of both bathrooms, new flooring, and fresh paint throughout, creating a bright and modern coastal retreat. The villa also features new windows and sliding doors, updated window treatments, all new furniture, and new TVs, along with a stylish mantle and electric fireplace that adds warmth and charm to the living space.

Check rates on Whimstay →