Hilton Head Island

Coastal South Carolina, twelve miles of Atlantic beach, and oak-shaded plantation communities.

5756 waterfront rentals·10 shores·Every listing on the water·Updated 2026-10-16

Hilton Head's foot-shaped barrier island sits just across the Georgia line. Gated plantation communities (Sea Pines, Palmetto Dunes, Shipyard) house most luxury rentals. Golf is everywhere, the beach is firm enough to bike, and October is the sweet spot for weather plus price.

StateSC
Peak seasonJune to August
Best forWaterfront stays
Featured254 rentals
The curated list · 254 rentals

Where we would stay in Hilton Head Island.

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Hilton Head Beach & Tennis Resort, Oceanfront, Tennis, Restaurants, Pickleball!
No. 241

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.

Seaside 278
No. 242

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.

Second-floor condo in beachfront complex with pools, tennis & gym
No. 243

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.

Spacious Villa with Balcony and Resort Amenities - Elegant Coastal Haven
No. 244

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!!

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Spacious Villa with Scenic Balcony and Resort Access - Stylish Coastal Haven
No. 245

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!!

Beach-view condo in oceanfront complex with outdoor pool, beach access, balcony
No. 246

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!

Seaside 358
No. 247

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.

Panoramic Views and Luxurious Amenities - Stunning Oceanfront Retreat
No. 248

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.

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254
curated rentals in Hilton Head Island
Dont Worry, Beach Happy 1BR Oceanview King Bed Villa in HHBT Resort
No. 249

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.

Stunning Views and Resort Amenities - Charming Oceanfront Haven
No. 250

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.

309 Breakers
No. 251

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.

231 Breakers
No. 252

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.

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Breakers 324 Oceanfront Hilton Head Condo Direct Beach Access
No. 253

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.

Coastal condo on the beach with panoramic views, beach access & a shared pool
No. 254

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.

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