Hilton Head Island

No. 37

102 Sea Cloisters Oceanfront First Floor Condo Walk out to beach from back deck King 2 Double

Condo

2 bedroom sleeps 4 Oceanfront private pool

Spacious holiday home with two bedrooms and two bathrooms, offering ocean views.

Check rates on Booking.com →

No. 38

Pool Access! Family Getaway in Hilton Head Resort

Apartment

2 bedroom sleeps 4 Beachfront private pool

Spacious Accommodations with beachfront access and pool facilities.

Check rates on Booking.com →

No. 39

Oceanfront 2BR Luxury - Balcony - Coligny Views

Apartment

2 bedroom sleeps 4 Beachfront private pool

Oceanfront 2BR Luxury offers breathtaking views with a spacious balcony.

Check rates on Booking.com →

No. 40

Our Cooler Getaway

Apartment

2 bedroom sleeps 4 Oceanfront private pool

Our Cooler Getaway is a spacious 2-bedroom, 2-bathroom vacation rental in Tybee Island.

Check rates on Booking.com →

No. 41

Oceanfront Villa w/ Pool Beach Access Hilton Head

Condo

2 bedroom sleeps 6 private pool

431 Captains Walk, A 2-bedroom, 2-bath villa with direct ocean views located in Palmetto Dunes Resort. Step off the 1st floor balcony and walk right to the pool or beach. Strong Wi-Fi should you need to work/school remotely. Enjoy Palmetto Dunes golf, tennis, pickleball, and the General Store when you stay here. Book today and enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. Enjoy stunning views of the Atlantic Ocean from your 1st floor private balcony overlooking the oceanfront pool.

Check rates on Whimstay →

No. 42

Oceanfront Villa w/Wrap Around Balcony Hilton Head

Condo

2 bedroom sleeps 7 private pool

1878 Beachside Tennis Villa, 2BR/2BA condo boasts breathtaking ocean and Calibogue Sound views and a wrap-around balcony. Located on the 4th floor, it provides easy access to South Beach Marina Village and The Salty Dog. The villa has been beautifully renovated and offers a comfortable, modern living space. Enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. A complete renovation! Who doesn’t love a gorgeous view? With this 2-bedroom, 2-bathroom villa, you get the perfect view of the Atlantic Ocean and the Calibogue Sound from the large wrap-around balcony. This will definitely become your vacation Happy Place!

Check rates on Whimstay →

No. 43

Lighthouse Point 20A

Apartment

2 bedroom sleeps 4 Beachfront private pool

Beachfront location with stunning sea views, featuring 2 bedrooms and outdoor swimming pool.

Check rates on Booking.com →

No. 44

Shorewood 311

Apartment

2 bedroom sleeps 6 Sea view private pool

Shorewood 311 in Hilton Head Island offers a spacious setting with two bedrooms and two bathrooms.

Check rates on Booking.com →

No. 45

Renovated condo on the beach with pool, balcony, central AC, W D, & fitness room

Condo

1 bedroom sleeps 6 private pool

HH Beach & Tennis 105A With a location right on the beach, a bright and spacious interior, and a furnished private balcony, this recently-renovated home is waiting to give you the fun-filled vacation you deserve! Spread out in the living room (with a new sofabed purchased in autumn 2021) and watch a good Netflix movie on the TV mounted just over the dining table with seating for guests. You'll love preparing delicious meals in the updated kitchen boasting full-size appliances, especially when you can enjoy them al fresco out on the balcony. The free WiFi will make it easy to download a new playlist to your device or research a fun outdoor adventure while the central AC cools down the room.

Check rates on Whimstay →

No. 46

Modern Ocean Villa A204. Renovated & Bright

Condo

1 bedroom sleeps 4 private pool

Newly updated and professionally designed, this 1BR villa offers a premium stay in the heart of Hilton Head. Guests love the ""A"" building location for its proximity to the waves and the stunning ocean views. The interior features a designer-tiled shower and a fully equipped kitchen with quartz surfaces. On-site, you’ll find 10 pickleball courts, a fitness center, and the island's largest oceanfront pool. Book now to enjoy modern comfort and effortless resort living. Welcome to Ocean Villa A204, a meticulously updated coastal retreat designed for the modern traveler.

Check rates on Whimstay →

No. 47

Beachfront Villa W/ Pool & Tennis Hilton Head

Condo

1 bedroom sleeps 6 private pool

B245 Hilton Head Beach and Tennis, Escape to coastal paradise at Hilton Head Beach and Tennis Resort! Enjoy direct beach access, poolside lounging, and tennis matches. Unwind in a sunny one-bedroom condo with a private balcony, fully equipped kitchen, smart TV, and WiFi. Explore nearby attractions like Folly Field Beach Park and Harbour Town Golf Links. Your seaside retreat awaits! Enjoy a vacation reimagined with the property manager, your trusted Hilton Head Island Property Management partner. Escape to a charming villa at the Hilton Head Island Beach and Tennis Resort and experience the ultimate beachside bliss!

Check rates on Whimstay →

No. 48

Walk to Beach: Hilton Head Condo w/ Screened Porch

Condo

2 bedroom sleeps 6 Beachfront private pool

Spacious Accommodations with direct access to the beach.

Check rates on Booking.com →

No. 49

Cozy Retreat with Oceanfront Pool and Tennis Courts - Charming Escape

Condo

1 bedroom sleeps 6 private pool

Escape to paradise at this cozy condo nestled within a sprawling 50-acre oceanfront resort, offering the island's largest oceanfront pool, 14 tennis and pickleball courts, beach volleyball, a fitness center, corn hole, basketball, racquetball, and more. Just a breezy 8-minute walk to Folly Field Beach along the resort's beautiful paths, with onsite dining, seasonal entertainment, walking trails, and wildlife viewing, there's something for everyone here. Whether you're planning a family beach vacation or an active tennis getaway, this villa creates the perfect setting for unforgettable Hilton Head memories.

Check rates on Whimstay →

No. 50

Shorewood 438

Apartment

2 bedroom sleeps 6 Beachfront private pool

Shorewood 438 in Hilton Head Island offers direct beachfront access and stunning sea views.

Check rates on Booking.com →

No. 51

Balcony, Pool Access and Tennis Courts - Charming Coastal Retreat

Condo

1 bedroom sleeps 4 private pool

This one-bedroom villa is conveniently located on the first floor of Ocean Villas A. This Villa is fully equipped with a kitchenette, dining/living area with a sleeper sofa. The master bedroom is furnished with a queen size bed, and its own TV. A laundry room is conveniently located just a few steps down the hall. 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. 52

Port II Villas 1613

Condo

2 bedroom sleeps 6 Ocean View

Port II Villas 1613 in Hilton Head Island offers a spacious setting with two bedrooms and three bathrooms.

Check rates on Booking.com →

No. 53

Spacious Villa with Balcony and Pool Access - Charming Coastal Getaway

Condo

1 bedroom sleeps 4 private pool

The spacious one bedroom, one bath villa that can sleep 4 people is located on the second floor of Ocean Villa A building. The villa has a fully equipped kitchen/dining area with a queen sleeper sofa. The master bedroom is furnished with a queen size bed. Enjoy your morning coffee on the balcony then venture out to the beach, pool or tennis courts that are only steps away!! Ocean View - Ocean Villas A244 Professionally Managed by HHB&T Vacation Rentals HHB&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. 54

Homey condo with ocean views balcony pool & easy beach access

Condo

2 bedroom sleeps 6 Beachfront private pool

Beachfront location with ocean views and easy beach access.

Check rates on Booking.com →

No. 55

Balcony, Pool, and Tennis Court Access - Spacious 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 Building B. This 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. 56

Ocean Access and Elegant Amenities - Charming Coastal Haven

Condo

1 bedroom sleeps 6 private pool

This beautiful one bedroom villa is located on the third floor of Ocean Villa A building. There is a fully equipped kitchen, dining area, and living room with a sleeper sofa. The bedroom features a queen size bed, ceiling fan, and a smart TV. NEWLY renovated bathroom featuring walk in shower! (Spring 2026) There are also two captain bunks, great for children! You'll have your own balcony to enjoy or you can take a short walk to the beach.

Check rates on Whimstay →

No. 57

Fully Equipped Kitchen and Access to Pool and Beach - Spacious 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 building B. This villa has a fully equipped kitchen, dining room, and living room 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 private, furnished balcony, then venture out to the beach, pool, tennis or pickleball courts that are only steps away!!

Check rates on Whimstay →

No. 58

Spacious Villa with Balcony and Resort Amenities - Charming Coastal Haven

Condo

1 bedroom sleeps 6 private pool

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

Check rates on Whimstay →

No. 59

Scenic Balcony and Access to Pools - Charming Coastal Getaway

Condo

1 bedroom sleeps 6 private pool

This beautiful one-bedroom villa is located on the third floor of Ocean Villas B. The master bedroom is furnished with a queen size bed. A set of captains bunks are located in the hallway perfect for children! The living area is equipped with a sleeper sofa. There is a fully equipped kitchenette to give you all the comforts of home. Enjoy the view from the furnished balcony or take a short walk to the beach or pools!

Check rates on Whimstay →

No. 60

Balcony and Access to Stunning Beach Activities - Beautiful Coastal Haven

Condo

1 bedroom sleeps 4 private pool

This beautiful upgraded one-bedroom villa is in the Ocean Villas. There is a fully equipped kitchen, dining area/living area with a queen sleeper sofa in the living room. The bedroom is furnished with a king bed. You have your own balcony to enjoy or you can take a short walk to the beach. Resort View - Ocean Villas A240 Professionally Managed by HHB&T Vacation Rentals HHB&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 out our website or visit our Welcome Desk for today's Special Offers!

Check rates on Whimstay →

No. 61

Balcony, Pool Access and Tennis Courts - Charming Coastal Oasis

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. This villa has a fully equipped kitchen, dining/living area with a queen 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, tennis courts and playground that are only steps away!!

Check rates on Whimstay →

No. 62

Scenic Balcony and Fully Equipped Kitchenette - Charming Coastal Retreat

Condo

1 bedroom sleeps 6 private pool

This lovely one-bedroom villa is located on the third floor of Ocean Villas C Bldg. There is a fully equipped kitchenette, dining/living area with sleeper sofa. The master bedroom is furnished with a queen size bed, and the children can enjoy a night's rest in the captain bunks. Enjoy the views from the furnished balcony or take a short walk to the beach, pools or courts! Resort View - Ocean Villas C302 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. 63

Private Balcony and Resort Amenities - Beautiful Coastal Retreat

Condo

1 bedroom sleeps 6 private pool

This beautiful one bedroom is located in the Ocean Villas. There is a fully equipped kitchen, dining area and a living room. The living room is furnished with a sleeper sofa. The bedroom is furnished with a queen bed, and there are two captain bunk beds right outside the bedroom perfect for the young children. You can sit on your own private balcony and enjoy the views or take a short walk to the beach.

Check rates on Whimstay →

No. 64

Balcony, Pool Access and Tennis Courts - Spacious 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. This villa has a fully equipped kitchen with full size appliances, a comfortable living area with a sleeper sofa, and up to date furnishings and decor throughout. The master bedroom is furnished with a queen size bed and smart TV. There are 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. 65

Spacious Villa with Balcony and Resort Amenities - Charming Coastal Escape

Condo

1 bedroom sleeps 6 private pool

This spacious one-bedroom, one-bath villa is located on the second floor of Ocean Villa, Building C. The villa features a fully equipped kitchen, dining area, and comfortable living space with a queen sleeper sofa. The primary bedroom is furnished with a queen-size bed, and a set of captain’s bunks in the hallway provides additional sleeping space that’s perfect for children. Begin your morning with coffee on the private balcony as the sun rises in brilliant color over the ocean, peacefully removed from parking lot noise. The gentle calls of seabirds and the sight of pelicans gliding overhead enhance the serene coastal ambiance.

Check rates on Whimstay →

No. 66

Balcony and Access to Resort Amenities - Spacious Coastal Retreat

Condo

1 bedroom sleeps 6 private pool

This spacious one bedroom, one bath villa is located on the third floor of Ocean Villa Building A. This 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. 67

Fairytale Escape w/ Pool, Tennis Golf Hilton Head

Condo

1 bedroom sleeps 4 shared pool

1651 St. Andrew's Common, Step into 'Happily Ever After' in Hilton Head! Play golf, hit the beach, and enjoy a shared pool and tennis court. Unwind in a sunlit living room, cook in a full kitchen, and sleep like royalty. Book now for your fairy tale vacation! Small dogs (1 max) are allowed up to 25 lbs. Welcome to ""Happily Ever After,"" where fairy tales meet modern luxury in Hilton Head! Tucked amidst the island's enchanting charm, this elegant villa is your gateway to a vacation straight out of a storybook. Tee off at multiple golf courses, frolic on sandy beaches, and unleash your competitive spirit with a game of tennis, all just minutes away from your royal abode!

Check rates on Whimstay →

No. 68

Breakers 215

Apartment

1 bedroom sleeps 4 Beachfront private pool

Breakers 215 in Hilton Head Island offers direct beachfront access and stunning sea views.

Check rates on Booking.com →

No. 69

Spacious Villa with Balcony and Resort Amenities - Charming Beach Haven

Condo

1 bedroom sleeps 6 private pool

The spacious one bedroom, one bath villa is located on the third floor of Ocean Villa C building. This 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. 70

Ocean-View Balcony: Beachfront Hilton Head Condo

Apartment

1 bedroom sleeps 4 Beachfront private pool

The entire place is yours with sea view and balcony.

Check rates on Booking.com →

No. 71

Panoramic Views and Luxurious Amenities - Gorgeous Oceanfront Escape

Condo

1 bedroom sleeps 5 private pool

DIRECT OCEANFRONT, TOP (THIRD) FLOOR Hilton Head Island Villa with PANORAMIC OCEAN AND BEACH VIEW, VIEW, VIEW!!! Imagine watching dolphins and listening to the waves from your private balcony with its expansive ocean and beach view in this clean, beautifully REMODELED, newly furnished and professionally decorated villa. Take in the outstanding view from the living room as you watch a movie on the 55"" Smart TV or use the free cable and high-speed internet. Staying on the top floor of this elevator and stair accessible three-story building enhances that ocean view with nobody above you.

Check rates on Whimstay →

No. 72

HH Beach & Tennis 226C

One-Bedroom Apartment

1 bedroom sleeps 4 Beachfront private pool

Beachfront location with direct access and a private pool.

Check rates on Booking.com →

No. 73

Furnished Balcony and Access to Tennis Courts and Pool - Charming Coastal Retreat

Condo

1 bedroom sleeps 2 private pool

This beautiful fully updated one-bedroom villa is located on the third floor of Ocean Villa B-Building. The master bedroom is furnished with a queen bed. There is a fully equipped kitchen. This villa sleeps 2 people. Have your morning coffee out on the furnished balcony or take a short walk to the beach, pool, tennis courts or playground!! Ocean View - Ocean Villas B337 Professionally Managed by HHIB&T Vacation Rentals STR Permit #072516 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. 74

Oceanfront Resort. Newly Renovated 1BR Villa

Condo

1 bedroom sleeps 6

Recently updated with high-end finishes, this first-floor villa at Hilton Head Beach & Tennis Resort is designed for comfort and style. Featuring a queen master, hallway bunks, and a sleeper sofa, it’s a versatile space for up to six guests. Take advantage of seasonal resort activities like poolside movies and karaoke, or explore the island’s world-class golf courses. Modern, clean, and steps from the sand, your perfect South Carolina vacation awaits. Step into a refined coastal sanctuary where every detail has been thoughtfully updated.

Check rates on Whimstay →

No. 75

Breathtaking Views and Resort Amenities - Gorgeous Oceanfront Villa

Condo

1 bedroom sleeps 6 private pool

Escape to this inviting fourth-floor oceanfront retreat in Admirals Row, where sweeping coastal views and soothing sea breezes create the perfect island getaway. This beautifully positioned one-bedroom villa offers a relaxing blend of comfort and charm just steps from the shoreline. The serene master bedroom features a plush queen-size bed, while cozy captain’s bunks tucked just outside the bedroom provide the perfect hideaway for children. A fully equipped kitchenette and charming eat-in dining area make it easy to enjoy casual meals after a day in the sun.

Check rates on Whimstay →

No. 76

Oceanfront Breakers 137 Condo w/ Sunrise Views!

Entire condo

1 bedroom sleeps 4 private pool

Near Golf Course. Coligny Beach On-Site<br /><br />Wake to the sound of waves and the sight of the Atlantic at this 1-bed, 1-bath condo! Perfect for couples or small families, this Hilton Head Island vacation rental offers direct beach access, a pool, and a private balcony overlooking the ocean. Spend the day at Coligny Beach or exploring shops and restaurants just steps away.

Check rates on Whimstay →

No. 77

Sea Side Villas II 288

Apartment

1 bedroom sleeps 4 Beachfront private pool

Comfortable Living: Sea Side Villas II 288 in Hilton Head Island offers a holiday home with one bedroom and a living room.

Check rates on Booking.com →

No. 78

Breakers 328 Oceanfront Hilton Head Condo. Stunning Beach View & Pool

Apartment

1 bedroom sleeps 4 private pool

Breakers 328 - Fully Renovated Oceanfront Top-Floor Condo. Private Balcony. Heated Pool. Walk to Coligny Plaza Breakers 328 is a completely renovated February 2026 top-floor oceanfront condo located directly on Coligny Beach, offering breathtaking panoramic views of the Atlantic Ocean from your private balcony. This beautifully updated villa combines modern coastal comfort, thoughtful design, and one of the most desirable beachfront locations on Hilton Head Island. This bright, inviting unit comfortably accommodates up to 6 guests and is ideal for couples, small families, snowbirds, and extended stays. New professional photos coming soon.

Check rates on Whimstay →

No. 79

HH Beach & Tennis 119C

Apartment

1 bedroom sleeps 4 Beachfront private pool

Beachfront location with direct access and stunning sea views.

Check rates on Booking.com →

No. 80

Waterfront condo with seasonal pools hot tub balcony AC & WD

Apartment

1 bedroom sleeps 4 Beachfront private pool

Beachfront location with seasonal pools, hot tub, balcony, AC & washer/dryer.

Check rates on Booking.com →

No. 81

Coastal Soul-Gorgeous Direct OceanFront!

Condo

1 bedroom sleeps 6

Wake up to breathtaking oceanfront views from this beautifully updated one-bedroom villa, yes, the balcony view is exactly as pictured! This cozy retreat features a king bed, children’s bunks, and a queen sleeper sofa, comfortably sleeping the whole family. The full kitchen is stocked with everything you need to cook at home. Just steps to the beach and a short walk to Coligny Plaza with shopping, dining, and entertainment close by. The Lowcountry Celebration Park is right across the street and is a great place for the kiddos as well as adults, lots of great bands and activities throughout the year. Best suited for a couple and 2-3 children max.

Check rates on Whimstay →

No. 82

Hampton Place 6504

Apartment

1 bedroom sleeps 4 Ocean view private pool

Spacious Accommodations in Hilton Head Island with sea views and two bathrooms.

Check rates on Booking.com →

No. 83

Scenic Patio and Resort Amenities - Exquisite Coastal Retreat

Condo

3 bedroom sleeps 6 shared pool

Nestled in the heart of the Queen's Grant community within renowned Palmetto Dunes, this two-story, pet-friendly villa offers a spacious retreat for up to 6 guests just steps from the Queen's Grant community pool. With a large outdoor patio, driving range views, and sandy beaches only 0.5 miles away, this home puts fine dining, marine adventures, golf, and racquet clubs all within easy reach. Whether you're planning a family getaway or a relaxed escape with your furry companion, this home creates the perfect setting for unforgettable Hilton Head memories.

Check rates on Whimstay →

No. 84

Breakers 225

Apartment

1 bedroom sleeps 4 Beachfront private pool

Breakers 225 in Hilton Head Island offers direct beachfront access and stunning sea views.

Check rates on Booking.com →

No. 85

Tennis Villa F14 - Beach and Pool

Condo

2 bedroom sleeps 6 private pool

Renovated Second Floor Villa with newer kitchen, 2 Bedrooms 2 Full Baths with room for 6. New wide luxury vinyl plank floors, solid surface countertops, open floor plan and a short 3 minute walk to the beach. New pull out sofa and beds. Our fall and winter promotions are in effect! Book 3 nights and get the 4th free, from September 2 through March 1st. Or be a snowbird and book 3 weeks to get the 4th free, from January 1st through March 1st. Holidays are excluded. Renovated Coastal 2nd Floor, 2-bedroom 2 bath beach villa located in the ocean front resort of Hilton Head Beach and Tennis.

Check rates on Whimstay →

No. 86

Breakers 237

Apartment

1 bedroom sleeps 4 Beachfront private pool

Breakers 237 in Hilton Head Island offers direct beachfront access and stunning sea views.

Check rates on Booking.com →

No. 87

Coastal Retreat: 4th Floor Balcony & Sunrises

Condo

2 bedroom sleeps 6 private pool

Perfectly situated on Hilton Head Island, this 2BR/2BA villa offers a modern, open-concept layout designed for comfort. The remodeled kitchen and spacious living area flow naturally to a double-sized deck overlooking the resort and ocean. Guests enjoy premium access to basketball courts, bike rentals, and the beach. Proximity to top-tier seafood dining and golf courses makes this an ideal choice for families and active travelers looking for a refined beachside experience. 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. 88

Renovated Luxury Villa w/ Patio & Pool Hilton Head

Condo

2 bedroom sleeps 7 shared pool

558 Queens Grant - Two bedroom and two bathroom villa. 2023 Renovation, Perfect family vacation spot in Palmetto Dunes! Community Pools, Easy walk to the beach. Enjoy the convenience of being close to Palmetto Dunes golf, tennis, pickleball, and the General Store when you stay here. Book today and enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. This just renovated villa is located in the Queen's Grant section of the Palmetto Dunes resort community and offers an ideal ground-floor locale with a private back patio and grill. The interior has vaulted ceilings, three smart TVs, and dual suites.

Check rates on Whimstay →

No. 89

Beachfront Saint Helena Island Condo w/ Amenities!

Apartment

1 bedroom sleeps 4 Beachfront private pool

Beachfront Saint Helena Island Condo w/ Amenities! offers direct beachfront access and stunning sea views.

Check rates on Booking.com →

No. 90

Harbor Island D112

Apartment

1 bedroom sleeps 4 Beachfront private pool

Located in Oceanmarsh Subdivision, this beachfront condo offers private beach access and amenities such as a swimming pool.

Check rates on Booking.com →

No. 91

Charming Oceanfront Escape with Heated Pools and Spa - Inviting Haven

Condo

2 bedroom sleeps 7 private pool

Retreat into a charming haven of 138 Shorewood, nestled within the exclusive oceanfront enclave of Shorewood. Immerse yourself in year-round relaxation with ton of amenities, including a zero-entry heated pool, kiddie pool, and spa. With direct beach access just moments away, delight in leisurely strolls and thrilling surfing adventures. Explore Coligny Plaza and Lowcountry Celebration Park with easy walks or bike rides minutes away. *The South Elevator (stack 35-39) is scheduled for upgrade in mid-November and will not be available for approximately 4 weeks* Make the most of your family vacation on Hilton Head Island!

Check rates on Whimstay →

No. 92

Savannah Beach & Racquet Club 323A

Condo

1 bedroom sleeps 2 Beachfront private pool

Comfortable Living: Savannah Beach & Racket Club 323A in Tybee Island offers a holiday home with one bedroom and one bathroom.

Check rates on Booking.com →

No. 93

Bluff Villas 1733

Apartment

1 bedroom sleeps 4 Beachfront

Bluff Villas 1733 in Hilton Head Island offers a spacious setting with one bedroom and a living room.

Check rates on Booking.com →

No. 94

Private Balcony and Resort Amenities - Charming Villa Retreat

Condo

2 bedroom sleeps 8 private pool

This is a lovely two bedroom two bathroom villa located in Bldg. G on the first floor. The master bedroom is furnished with a queen size bed. The second bedroom is furnished with a full size bed and a set of twin bunk beds. For additional sleeping there is a queen sleeper sofa located in the living room. The kitchen comes fully equipped with full-size stainless steel appliances. Enjoy the beautiful view from your furnished private balcony or enjoy a short walk to the beach, pool, tennis courts or playground.

Check rates on Whimstay →

No. 95

2nd floor Condo pool hot tub pickleball tennis & close to beach

Condo

1 bedroom sleeps 4 Beachfront private pool

Beachfront location with direct access to the beach.

Check rates on Booking.com →

No. 96

Hampton Place 5501

Apartment

1 bedroom sleeps 4 Beachfront private pool

Hampton Place 5501 in Hilton Head Island offers direct beachfront access and stunning sea views.

Check rates on Booking.com →

No. 97

Beachfront Villa With Ocean Views Hilton Head

Condo

2 bedroom sleeps 6 shared pool

Stunning oceanfront villa steps away from pristine beaches, Coligny Plaza, and island adventures. Featuring 2 bedrooms, 2.5 baths, and a fully-equipped kitchen. Relax on the patio, splash in the community pool, or stroll the lush grounds. Ideal for creating unforgettable Hilton Head memories. Book now for your dream vacation! Just steps to the white, sandy beaches, beautiful ocean views, and the pleasant sound of waves lapping against the seashore! This 2 bedroom, 2.5 bath villa in the prime location of South Forest Beach is new to the rental market. It has been very well taken care of with your enjoyment and comfort in mind and there's even a bonus powder room on the main level.

Check rates on Whimstay →

No. 98

Oceanfront Villa, Pool Prime Location! Hilton Head

Condo

2 bedroom sleeps 7 private pool

23 Ocean Club, Oceanside 2 bedroom, 2 bath villa. Lovely decor, spacious rooms, on-site pool and a leisurely walk to the boardwalk that takes you to the soft, white sandy beach and blue ocean. Strong Wi-Fi for working/schooling remotely. The Ocean Club Complex is Oceanfront with a private path to the beach. Enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. Can you imagine a lovely and relaxing home away from home to make your beach vacation memorable? Also, strong Wi-Fi easily accommodates working/schooling remotely, so stay awhile and enjoy the beach and other amenities when you wish.

Check rates on Whimstay →

No. 99

Oceanfront Condo! Breakers 210 w/ Sunrise Views

Apartment

1 bedroom sleeps 4 Beachfront private pool

The holiday home features a beachfront location and stunning sea views.

Check rates on Booking.com →

No. 100

Pool, Beach & Ocean View: Hilton Head Resort Condo

Condo

1 bedroom sleeps 4 Beachfront private pool

Comfortable accommodations with sea views, located steps from the beach.

Check rates on Booking.com →

No. 101

Oceanfront Villa w/ Rooftop Pool on Hilton Head

Condo

2 bedroom sleeps 6 private pool

Escape to a beautiful villa with a private rooftop pool and hot tub, just steps from the beach. Enjoy stunning ocean views and all the comforts of home during your stay. This 2-bedroom, 2-bathroom villa sleeps up to 6 guests and features a fully equipped kitchen, dining area, and private balcony. Explore the nearby Coligny Plaza or relax by the shared oceanfront pool. Book now for a vacation reimagined! Find everything your heart desires and more at this beautiful villa with unique rooftop pool and hot tub surrounded by an amazing deck. 101 North Shore Place is perfect for a short-term getaway, or a long-term stay where you can work remotely or attend classes online.

Check rates on Whimstay →

No. 102

Beach Access: Ocean-View Condo w/ Screened Balcony

Condo

1 bedroom sleeps 4 Ocean View private pool

Beach Access: Ocean-View Condo w/ Screened Balcony in Cedar Reef Villas offers direct access to the beach and features ocean views.

Check rates on Booking.com →

No. 103

Breathtaking Ocean Views and Resort Style Pools - Amazing Beachfront Oasis

Condo

2 bedroom sleeps 5 private pool

Escape to the ultimate beachfront living at the newly renovated 4205 Windsor Court, located in the prestigious Palmetto Dunes community. Revel in the best ocean views from every room and enjoy top-tier family amenities, including 2 beachfront pools, spa and convenient elevator access. Seconds from the beach! Explore nearby world-renowned golf and tennis facilities! Discover Your Dream Ocean Getaway With Us; Learn More Below! HIGHLIGHTS Stunning Views: One of the best unobstructed ocean views on the island, overlooking the Atlantic Ocean, the pool and lagoon with immaculate Lowcountry landscaping.

Check rates on Whimstay →

No. 104

Seaside 279

Condo

1 bedroom sleeps 4 private pool

Beautifully remodeled condo just steps from Hilton Head’s main beach! Enjoy ocean views from your private balcony and easy walking access to restaurants, shops, and entertainment. This cozy villa features a full kitchen, bikes, and beach chairs included for your stay. Freshly updated with stylish decor, smart TVs, and modern comforts. Direct beach access on property and just a short stroll to Hilton Head’s new Celebration Park, perfect for a fun, relaxing beach vacation! Please note that the condo is open concept so there is no door between the living room and bedroom.

Check rates on Whimstay →

No. 105

Seaside 102

Condo

1 bedroom sleeps 6 private pool

Escape to the perfect Hilton Head getaway! This charming first-floor, end-unit condo is just steps from the beach and a short stroll to Coligny Plaza, where you’ll find shopping, dining, and entertainment. Inside, you'll find a cozy and comfortable space with everything you need for a relaxing stay: Queen bed in the bedroom with a private AC unit Bunk beds in the hall - perfect for smaller kids Queen sleeper sofa for extra guests Full kitchen stocked with everything you need to cook a meal Best suited for a couple and 2-3 kids max. Outside, enjoy easy access to the beach and pool, plus complimentary beach chairs and bikes to explore the island!

Check rates on Whimstay →

No. 106

Seaside 386

Condo

1 bedroom sleeps 4 private pool

Enjoy stunning ocean views from this beautifully renovated villa, perfect for a relaxing beach escape. Features a COMFORTABLE King bed, Queen sleeper sofa, and a spa-style walk-in shower with rainfall and handheld sprayers. Kick back with a 55"" Roku TV in the living room and a 32"" Roku TV in the bedroom. The fully equipped kitchen has everything you need to cook a meal at home. All just steps to the beach! Location Highlights: Just 2 blocks from Coligny Plaza, with easy access to restaurants, shops, and entertainment. A short walk to Lowcountry Celebration Park with its playgrounds, events, and outdoor fitness trail.

Check rates on Whimstay →

No. 107

SerenityByTheSea-Couples Retreat-King,Bikes,Chairs

Condo

1 bedroom sleeps 4 private pool

Treat yourself to the ultimate Hilton Head escape in this beautifully decorated villa with incredible ocean views, just steps from the sand and walking distance to the island’s top restaurants, shops, and bars. Unwind in the king bedroom, refresh in the modern bath with a full standing shower, and enjoy the clean, contemporary look of LVP flooring throughout. The fully equipped kitchen is perfect for dining in, and the living room features a large smart TV for cozy nights in. Beach chairs, bikes, and beach gear are included, making this the ideal spot for a romantic retreat or relaxing beach getaway!

Check rates on Whimstay →

No. 108

Beautiful Couples Retreat Oceanview w/new bikes&Ch

Condo

1 bedroom sleeps 4 private pool

Beautifully renovated oceanview retreat, perfect for a romantic getaway or small family escape. Enjoy a king bed, queen sleeper sofa, driftwood tile floors, stainless steel appliances, shiplap walls, and barn doors that add charm and privacy. Take in stunning views from your private balcony, relax with included beach chairs, or explore the island on two complimentary bikes. Walk to shops, restaurants, and entertainment, everything you need for a memorable Hilton Head stay. 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. 109

Breakers 220 Hilton Head. Oceanfront. Heated Pool. Elevator. Renovated

Apartment

1 bedroom sleeps 4 private pool

Breakers 220 is a beautifully renovated oceanfront condo located in the heart of Coligny Beach on Hilton Head Island. This upgraded one bedroom, one bathroom unit offers a private balcony with sweeping ocean views, direct beach access, and access to a heated pool and children’s pool. The interior features a premium Saatva queen mattress, a comfortable leather sleeper sofa, a cozy bunk area for kids, and Roku Smart TVs. The fully equipped kitchen includes stainless steel appliances, cookware, coffee maker, Keurig, and dining space for six. Guests also enjoy the convenience of an in-unit washer and dryer, high-speed Wi-Fi, air conditioning, ceiling fans, and quality linens.

Check rates on Whimstay →

No. 110

Seaside 357

Condo

1 bedroom sleeps 4 private pool

Wake up to breathtaking ocean views in this beautifully renovated 3rd-floor villa, the perfect escape for two. Enjoy an open-concept design with a plush King bed, cozy Queen sleeper, a fully equipped modern kitchen, and a spa-style walk-in shower. Sip coffee on your private balcony, stroll the beach just steps away, or bike to nearby shops and restaurants, beach chairs and bikes included for your adventure. 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. 111

Oceanfront Luxury Villa w/ Pool on Hilton Head

Condo

1 bedroom sleeps 4 private pool

405 Windsor Place - Beautifully furnished 4th floor, 1BR/2BA end-unit villa with dramatic ocean view. This popular villa has everything you need to make your beach and island vacation the best ever! Strong Wi-Fi for working/schooling remotely. Enjoy the convenience of being close to Palmetto Dunes golf, tennis, pickleball, and the General Store when you stay here. Book today and enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. Enjoy dramatic views of the Atlantic ocean from your private balcony overlooking an oceanfront pool (pool is only heated in March and April) with a spa, a barbecue area, and children's pool!

Check rates on Whimstay →

No. 112

Oceanfront Villa. Heated Pool. South Forest Beach

Entire condo

1 bedroom sleeps 6 private pool

Welcome to the Island! Relax and enjoy our direct oceanfront, pool front, one bedroom, one bathroom, beautiful beach villa. Look out your balcony and see nothing but ocean water! Listen to the waves on your spacious, private balcony, while soaking up the sun during the day or relaxing & star gazing at night. You will enjoy the wonderful accommodations and convenient location very close to the popular Coligny Plaza with spectacular views at Ocean Dunes!<br /><br /><b>The space</b><br /> Add my listing to your wishlist by clicking the in the upper-right corner <br /><br /> Private gated community<br /> Beachfront HEATED POOL - Open all year round!<br /> Onsite Resort Cafe / Tiki Bar & Grille...

Check rates on Whimstay →

No. 113

Bluff Villas 1799

Condo

sleeps 4 Water View

Bluff Villas 1799 in Hilton Head Island offers comfortable accommodations with a water view.

Check rates on Booking.com →

No. 114

Pools + Sundeck: Beachfront Hilton Head Condo!

Entire condo

3 bedroom sleeps 9 private pool

Set out on a beachy retreat and stay at this 3-bedroom, 2-bathroom vacation rental condo nestled in The Hilton Head Resort. You’ll have access to community amenities like 2 outdoor pools, an indoor pool & hot tub, tennis & pickleball courts, sundeck, sauna, fitness center, and more! Walk a quarter mile or take the golf cart to the beach, grab happy hour, pick up a game of sand volleyball at Coco’s right off the coast, rent bikes to ride around the island, or book a tee time at a golf course!<br /><br /><b>The space</b><br />Step-Free Access. Proximity to Beaches. Wet Bar <br /> <br />Bedroom 1: Queen Bed. Bedroom 2: Queen Bed. Bedroom 3: Full Bed, Twin Bed.

Check rates on Whimstay →

No. 115

Oceanfront Villa, Resort Amenities on Hilton Head

Condo

3 bedroom sleeps 8 private pool

307 Shorewood, This 3-BR, 3-BA oceanfront villa is located in the prime South Forest Beach area, steps away from the beach and close to Coligny Plaza and Celebration Park. The villa offers a great pool, perfect for relaxation. With a corner location, you can enjoy stunning views of the ocean. The villa is perfect for a family or group of friends looking for a luxurious beach vacation. Enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. The soft white sands and warm waves of South Carolina's coastline are among the best in the world, and you deserve the best!

Check rates on Whimstay →

No. 116

Modern Beachfront Bliss: 2BR/2BA Luxury Villa

Condo

2 bedroom sleeps 6 private pool

Elevate your beach vacation in this designer-renovated Hilton Head villa. Featuring an open floor plan and a custom kitchen with granite finishes, it is designed for effortless entertaining. Step out onto the massive deck to catch glimpses of the ocean or walk down the direct beach path for a day in the surf. This resort-based gem offers bike rentals, picnic areas, and proximity to Hilton Head's famous trail system. Book your stay where luxury meets the Low Country. 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 the property at this time.

Check rates on Whimstay →

No. 117

Admiral's Row 309: Beachfront Luxury Living

Condo

2 bedroom sleeps 6 private pool

Experience the ultimate Hilton Head getaway in this 3rd-floor oceanfront villa. Admiral’s Row 309 offers breathtaking views from a double-sized balcony and a modern coastal interior featuring a bright quartz kitchen. Perfect for families, the villa sleeps six and provides direct access to the island’s best beaches, on-site dining, and the largest oceanfront pool on the island. 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. 118

Balcony Overlooking Tennis Courts and Resort Amenities - Charming Villa Escape

Condo

2 bedroom sleeps 6 private pool

This beautiful two-bedroom villa is in the Tennis Villas. There is a fully furnished kitchen, dining area, and living room. The living room is furnished with a sleeper sofa. The master bedroom is furnished with a queen bed. The guest room is furnished with two twin beds. There are also two bathrooms. You have your own balcony overlooking the tennis courts. Tennis Villas G19 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. 119

Luxury Beachfront Villa w/ Pool, on Hilton Head

Condo

2 bedroom sleeps 8 private pool

2 Ocean Club, A 2 bedroom, 2 bath villa located within steps of the ocean in the South Forest Beach area of Hilton Head Island. Make your island dreams come true here! Strong Wi-Fi accommodates working/schooling remotely. The Ocean Club Complex is Oceanfront with a private path to the beach. Enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. Get ready to be amazed by the NEWLY RENOVATED Primary Bath and the cozy bunk beds in the 2nd bedroom! This villa has gone through many new updates to make your stay more comfortable and enjoyable. Check out the latest photos now!

Check rates on Whimstay →

No. 120

Oceanfront with Pool & Beach Access Hilton Head

Condo

2 bedroom sleeps 6 shared pool

Luxurious Oceanview villa with exceptional amenities on Hilton Head Island. 1405 Seacrest has stunning views, resort pools, private beach access, and remote work-friendly Wi-Fi during exterior renovations. Perfect for a relaxing beach vacation or extended stay. Book now for an unforgettable getaway! You deserve to spoil yourself with luxurious accommodations on your beach vacation! Also, strong Wi-Fi makes this the perfect location to stay awhile, work/school remotely, and then head to the beach or enjoy other island adventures.

Check rates on Whimstay →