Hilton Head Island

No. 361

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. 362

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. 363

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. 364

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. 365

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. 366

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. 367

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. 368

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. 369

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. 370

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. 371

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. 372

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. 373

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. 374

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. 375

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. 376

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. 377

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. 378

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. 379

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. 380

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. 381

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. 382

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. 383

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. 384

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. 385

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. 386

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. 387

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. 388

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. 389

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. 390

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. 391

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. 392

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. 393

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. 394

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. 395

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. 396

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. 397

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. 398

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. 399

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. 400

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. 401

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. 402

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. 403

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. 404

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. 405

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. 406

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. 407

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. 408

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. 409

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. 410

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. 411

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 →