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Vacation rentals in Hilton Head Island

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Popular amenities for Hilton Head Island vacation rentals

Self check-in
Pet friendly
Monthly stays
Laptop-friendly workspace
Gym

Home rentals in Hilton Head Island

Top guest favorite
A well-lit bedroom features two spacious beds, each adorned with vibrant blue and green bedding. A decorative wall basket adds a natural touch, while a window with patterned curtains allows for natural light. A small chair and side table enhance the room's functionality.
Home in Hilton Head Island
4.99 out of 5 average rating, 76 reviews

6 BR, Sleeps 26, Beach Time

Top guest favorite
A charming two-story house is presented with a light exterior and a welcoming orange door. The covered porch features white railings and multiple seating areas. Lush greenery surrounds the home, enhancing its outdoor space, while a clear blue sky with scattered clouds creates a pleasant backdrop.
Home in Bluffton
4.99 out of 5 average rating, 107 reviews

Beautiful home with pond view and free Golf Cart!

Top guest favorite
The charming cottage features a low country style exterior with reclaimed wood siding and a corrugated metal roof. A welcoming front porch is adorned with seating. Surrounding landscaping includes shrubs and trees, enhancing the serene setting within the historic district.
Home in Bluffton
4.99 out of 5 average rating, 371 reviews

Bluffton Farm Cottage: Come for Summer Vacation

Guest favorite
The exterior of the home is showcased at dusk, featuring a spacious heated pool illuminated in blue. Surrounding the pool are multiple lounge chairs, providing a serene outdoor space for relaxation. The multi-level structure is elegantly designed, with expansive balconies above and a well-lit entrance.
Home in Hilton Head Island
4.95 out of 5 average rating, 79 reviews

5 Bedroom-Beach Access-Pool-Sleeps 14!

Guest favorite
The living room displays a light, airy ambiance with large sliding glass doors leading to a private balcony. A plush couch is complemented by decorative pillows, and a patterned ottoman adds texture. Natural light filters through the windows, enhancing the inviting atmosphere.
Home in Hilton Head Island
4.88 out of 5 average rating, 34 reviews

~Couples Paradise~Villa W/Pool~Beachfront Resort

Superhost
A modern two-story home is nestled among lush trees, featuring a large outdoor pool surrounded by a paved deck. A spacious covered balcony offers seating, providing a view of the inviting pool area and landscaped grounds, perfect for relaxing or entertaining.
Home in Hilton Head Island
5 out of 5 average rating, 4 reviews

Modern Beach Escape | Private Pool~Steps to Beach

Superhost
The entrance of the cottage features a light blue door surrounded by a wooden deck, framed by lush greenery and tall trees. A small sign reading 'Home' hangs next to the door, indicating a welcoming atmosphere.
Home in Hilton Head Island
4.78 out of 5 average rating, 23 reviews

17 Night Heron · Elegant, Stylish Beach Cottage

Guest favorite
A serene outdoor space features a private plunge pool surrounded by a concrete deck. Lounge chairs are positioned nearby, and a dining table with an umbrella is visible on the grassy edge, flanked by landscaping under a twilight sky.
Home in Hilton Head Island
4.93 out of 5 average rating, 14 reviews

FREE Pool Heat - Luxury Home - Pet Friendly

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Pet-friendly vacation rentals in Hilton Head Island

Superhost
A charming cottage exterior is shown with a wrapped entryway and steps leading to the front door. Surrounding greenery and trees create a serene environment. A fan is mounted on the wall, and the large window allows for natural light into the living space.
Hut in Hilton Head Island
4.83 out of 5 average rating, 161 reviews

SEA PINES-Bike to Beach, Dog Friendly Cottage

Top guest favorite
The exterior of the cottage is depicted, showcasing a two-story design with light-colored siding, surrounded by landscaped shrubs and greenery. A pathway leads to the entrance, flanked by a wooden railing, inviting access to the home.
Cottage in Hilton Head Island
4.96 out of 5 average rating, 101 reviews

Shipyard! - Private Beach & Golf! Pet Friendly!

Guest favorite
An open living area showcases a soft, L-shaped couch and a round coffee table. A dining area with white furniture is visible next to a fully equipped kitchen featuring stainless steel appliances and mosaic tile backsplash. Natural light filters through a nearby window, highlighted by ceiling fans.
Condo in Hilton Head Island
4.8 out of 5 average rating, 5 reviews

Cordillo Cabanas D4 – Coastal Escape Near Beach!

Superhost
A bright living room features a blue sofa, a comfortable armchair, and a wooden coffee table. Large windows provide views of the surrounding nature, while a fireplace is positioned against a red-tiled wall. A flat-screen TV sits atop a wooden stand.
Villa in Hilton Head Island
4.76 out of 5 average rating, 107 reviews

Shipyard, Beach, Golf, Tennis, Quiet End Unit

Guest favorite
Bright blue umbrellas are seen shading wooden chairs on a sandy beach. Two bicycles are parked nearby, with gentle waves and an expansive ocean in the background. A tranquil atmosphere is created by the soft beach grass and light shoreline.
Apartment in Hilton Head Island
4.91 out of 5 average rating, 161 reviews

Hilton Head Beach Getaway

Guest favorite
A serene pool area is surrounded by lush greenery, with a paved walkway leading to the water. Several lounge chairs are positioned near the pool, which is framed by a low fence. Mature trees provide ample shade, enhancing the tranquil atmosphere.
Condo in Hilton Head Island
4.85 out of 5 average rating, 155 reviews

1 Bedroom Condo, 5 Minute Walk to the Beach

Top guest favorite
The bungalow is nestled among lush greenery and tall trees, surrounded by a natural environment. Palm leaves frame the structure, and a small deck is visible at the front, inviting warmth and privacy in this woodland setting.
Bungalow in Hilton Head Island
4.95 out of 5 average rating, 100 reviews

Closest to Beach Path, Screened Porch, 1 dog ok

Guest favorite
The open living area features new reclining furniture arranged around a coffee table. A flat-screen TV is positioned on a media console against the wall. Light-colored tiles and a patterned area rug enhance the spaciousness, complemented by a ceiling fan and decorative shelving.
Villa in Hilton Head Island
4.89 out of 5 average rating, 100 reviews

Walk to the Beach, One Level Villa, COMFY beds

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Pet-friendly houses in Hilton Head Island

Top guest favorite
A modern treehouse is framed by lush greenery, showcasing large windows that invite natural light. A ramp leads to a spacious deck, providing access to the entry. The surrounding area features mature trees and tropical plants, enhancing the serene environment.
Home in Hilton Head Island
4.99 out of 5 average rating, 82 reviews

180º Ocean Views, Treehouse "Siren's Lookout"

Superhost
An outdoor deck features a shapely pool surrounded by lounging chairs. Lush greenery and palm trees are visible in the background, offering a view of the golf course. A purple umbrella stands next to the pool, providing shade.
Home in Hilton Head Island
4.85 out of 5 average rating, 128 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Top guest favorite
A spacious living area features high ceilings with exposed beams, large windows allowing natural light, and a comfortable gray sofa. Two patterned armchairs are positioned opposite a circular coffee table, complemented by a soft blue area rug. A dining area is visible in the background.
Home in Hilton Head Island
5 out of 5 average rating, 64 reviews

Harbour Town Treehouse | Deer Island | Sea’Forever

Guest favorite
An inviting living space features a sectional sofa, a wooden coffee table, and a dining area with several chairs. Natural light illuminates the room through multiple windows, highlighting the coastal-inspired decor and airy layout. A chandelier complements the open, relaxed atmosphere.
Home in Hilton Head Island
4.94 out of 5 average rating, 114 reviews

Cozy Coastal Chic - Beach, Pickleball, Golf, Pets

Guest favorite
A spacious screened porch equipped with a dining table and chairs offers a relaxing area for gatherings. Two ceiling fans provide comfort, and a fireplace adds a cozy touch. A large window showcases the private backyard, enhancing the connection to the outdoors.
Home in Hilton Head Island
4.85 out of 5 average rating, 214 reviews

Private Beach Access-Pet Friendly-Hot Tub!

Guest favorite
A two-story house features a light-colored exterior with a metal roof and a front balcony. The driveway provides access to two garages, with landscaped greenery and grass surrounding the property, enhancing the overall curb appeal.
Home in Hilton Head Island
4.86 out of 5 average rating, 371 reviews

W2Bch*4TVs*1GIG I*PetsWC *WiFi*4King ßds*grill*gms

Top guest favorite
A two-story light blue house with gray shutters is shown, set within a wooded area. A six-passenger golf cart is parked in the driveway, adding convenience for guests. Surrounding landscaping includes mulch and native plants, creating a natural setting.
Home in Hilton Head Island
4.95 out of 5 average rating, 158 reviews

Heated Pool/Fenced Yard, Golf Cart rental - 79

Top guest favorite
A spacious bedroom features a large bed dressed in neutral linens, flanked by light wood nightstands with lamps. Natural light floods in through multiple windows and skylights. A cozy seating area with light-colored cushions and decorative pillows provides additional comfort.
Home in Bluffton
4.98 out of 5 average rating, 159 reviews

Old Town Bluffton Cottage + FREE Golf Cart!

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Quick stats about vacation rentals in Hilton Head Island

  • Total rentals

    6.2K properties

  • Nightly prices starting at

    R181 ZAR before taxes and fees

  • Total number of reviews

    130K reviews

  • Family-friendly rentals

    5K properties are a good fit for families

  • Pet-friendly rentals

    970 properties allow pets

  • Rentals with a pool

    5.5K properties have a pool

Your guide to Hilton Head Island

All About Hilton Head

There are 24 golf courses and 12 miles of soft-sand beaches spread over Hilton Head Island’s 25,000 acres. Add scenic walking trails, breezy, tropical weather, and an obsession with tennis and there’s a good chance you’re here to recreate and relax. This is an island of swaying palms, easy resort-style living, and the Southern flare for hospitality for which this neck of the woods is known. Hilton Head Island is also steeped in history, with a prominent Gullah-Geechee influence that infuses this little corner of the lowcountry with a cultural richness. There are also restaurants serving traditional Southern fare, oyster shucking stalls, and folk music and artisan wares steeped in West African tradition. With so much layered history everywhere you look, you may have come here to play, but you’ll likely leave having learned a lot too.

The best time to stay in a vacation rental in Hilton Head Island

If you want to visit Hilton Head Island at its busiest and most lively time of year, come during the high summer months of June, July, and August. A golf tournament every spring draws throngs of visitors, but otherwise April and May tend to be quieter times to enjoy the calmer side of island life. Visiting in September or October will also mean mild weather and few crowds, though be careful to check the hurricane forecast as tropical storms can hit in late-autumn. The Island quiets down throughout the winter, and if you choose to come at this time of year, you may just find yourself with a 25,000 acre private island resort at your fingertips — though know that it won’t be the best time for swimming in the ocean.

Top things to do in Hilton Head Island

Learn about Gullah culture

The Gullah-Geechee people of Hilton Head and the surrounding lowcountry are the descendants of enslaved West Africans who, due to the remoteness of their island plantations, managed to preserve their heritage and cultural identity throughout the centuries. Take a boat tour along the waterways that link these island communities, go on a trail walk led by a Gullah elder, or savor Gullah culture in one of the best ways possible — by tasting its influence on so much of Southern cuisine.

Golf

With two dozen golf courses on Hilton Head Island, you can rest assured that this is an excellent place to putt. The island is something of a pilgrimage site for golf aficionados, with the pros and fans alike coming down every year for the regular pro tours and annual tournaments. Note that some of the island’s golf clubs are private or membership only, but fear not, there are still more than 15 public courses that anybody can enjoy.

Sea Pines Forest Preserve

Sea Pines Forest Preserve is a haven of natural beauty, wildlife, and history. Wander along wetland boardwalks, hike through forest trails, and watch alligators bask in the marshes. While here, don’t miss the 4,000-year-old Sea Pines Shell Ring, an important indigenous archeological site, and leave some time to get lost in the secret forest, past a vanishing swamp.

Frequently Asked Questions

  • How is the weather in Hilton Head Island?

    Hilton Head Island experiences a subtropical climate. Summers are hot and humid with temperatures around 90°F (32°C), while winters are mild with temperatures around 60°F (15°C). Rainfall is evenly spread throughout the year.

  • What are some of the best things to do in Hilton Head Island?

    Visitors frequently enjoy exploring the Island's pristine beaches, playing golf on its world-class courses, cycling along the numerous bike trails, and observing wildlife at the Pinckney Island National Wildlife Refuge.

  • What is the best time of year to visit Hilton Head Island?

    Spring and summer, particularly April through June, are the most popular times to visit Hilton Head Island. This period coincides with pleasant weather and popular events such as the RBC Heritage PGA golf tournament in April and the Hilton Head Island Art Festival in May.

  • What are the best places to stay in Hilton Head Island?

    Popular areas to stay on Hilton Head Island include the Sea Pines Resort area with its golf courses and beaches, the Palmetto Dunes Oceanfront Resort area for its central location, and the Harbour Town area known for its iconic lighthouse.

  • What are the best places to visit in Hilton Head Island?

    Coligny Beach Park, Sea Pines Forest Preserve, and the Harbour Town Lighthouse are popular places to visit in Hilton Head Island. The Coastal Discovery Museum is also frequently suggested for those interested in local history and ecology.

  • What are some hiking trails in Hilton Head Island?

    Hilton Head Island has several hiking trails such as those found in Sea Pines Forest Preserve, Fish Haul Creek Park, and Jarvis Creek Park. These trails offer opportunities to explore the island's diverse flora and fauna.

  • What are some family activities to do in Hilton Head Island?

    Families can explore interactive exhibits at the Sandbox, an interactive children's museum, enjoy a dolphin-watching tour, visit the Coastal Discovery Museum, or bike along the many pedestrian-friendly trails on the island.

  • What are some of the best day trip ideas in Hilton Head Island?

    Popular day trips from Hilton Head Island include exploring the historic city of Savannah, Georgia, immersing in the natural beauty of Beaufort, South Carolina, and discovering the rich cultural heritage of the Gullah Geechee Corridor.

  • Are there vacation rentals with a dedicated workspace in Hilton Head Island?

    Yes! Work meets play with ease at over 3,010 vacation rentals in Hilton Head Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in boutique hotel rentals in Hilton Head Island?

    Experience the best of Hilton Head Island with our boutique hotel rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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