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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 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, 370 reviews

Bluffton Farm Cottage: Come for Summer Vacation

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 Sea Pines
4.99 out of 5 average rating, 82 reviews

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

Top 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 Palmetto Dunes
4.94 out of 5 average rating, 113 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, 213 reviews

Private Beach Access-Pet Friendly-Hot Tub!

Guest favorite
A private pool area is framed by lush greenery and palm trees, featuring a turquoise swimming pool with a pink float. Two sun loungers are positioned beside the pool, with a shaded cabana offering seating and a dining area.
Home in Hilton Head Island
4.98 out of 5 average rating, 109 reviews

New Resort-Style Pool, Cute House 88 Steps to Sand

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

Guest favorite
A shaded balcony is furnished with two woven chairs and a small table, complemented by a decorative area rug. Lush greenery is visible beyond the railing, providing a natural backdrop, while large windows allow for ample light to fill the space.
Home in Hilton Head Island
4.97 out of 5 average rating, 110 reviews

Cozy beach house w/Private Heated Pool near park

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Pet-friendly vacation rentals in Hilton Head Island

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, 100 reviews

Shipyard! - Private Beach & Golf! Pet Friendly!

Superhost
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 Sea Pines
5 out of 5 average rating, 4 reviews

Cordillo Cabanas D4 – Coastal Escape Near Beach!

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, 160 reviews

Hilton Head Beach Getaway

Top guest favorite
A comfortably arranged living room features a blue sofa and loveseat facing a coffee table. A mounted flat-screen TV is positioned on an entertainment console. Large glass doors open to a balcony, allowing natural light to illuminate the space. A dining area is visible in the background.
Condo in Sea Pines
4.93 out of 5 average rating, 14 reviews

Sea Pines 2 Bdrm/2Ba Condo W/Bikes, Pets Welcome!

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

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 Palmetto Dunes
4.89 out of 5 average rating, 100 reviews

Walk to the Beach, One Level Villa, COMFY beds

Superhost
The rear view of the house showcases a spacious deck with outdoor seating and a shaded area under an umbrella. A newly built pool, featuring a tanning ledge, sits adjacent to the deck. Lush greenery and tall trees frame the serene outdoor setting.
Home in Sea Pines
5 out of 5 average rating, 4 reviews

120 Club Course @ Sea Pines | Lagoon View | Pool

Superhost
A charming two-story house is set against a backdrop of trees, featuring large windows that allow natural light to fill the interior. A welcoming front porch is highlighted by white rocking chairs, and a fenced yard offers a sense of privacy. Additional structures are visible in the background.
Cottage in Bluffton
4.81 out of 5 average rating, 253 reviews

Bluffton Retreat, Pets Welcome.

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Pet-friendly houses in Hilton Head Island

Guest favorite
The open-concept living space features handmade Saltillo tiles and a vaulted ceiling. A comfortable couch and a fireplace are visible along with a large dining table. A staircase leads to the upper level, enhancing the spacious layout. Sliding glass doors provide access to the outdoor area.
Home in Sea Pines
4.98 out of 5 average rating, 86 reviews

Governor’s Quarters: Stately Sea Pines Stay on HHI

Top guest favorite
A private pool area is visible, surrounded by lush greenery. Sun loungers are arranged around the pool, providing a comfortable space for relaxation. The exterior of the house features a light-colored facade, with large windows that invite natural light into the home.
Home in Sea Pines
5 out of 5 average rating, 10 reviews

Pets ~ Upscale Decor ~ Private Pool ~ Fenced Yard

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 Palmetto Dunes
4.85 out of 5 average rating, 127 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Superhost
A spacious living area is illuminated by natural light streaming through large windows. Comfortable couches are arranged around a central coffee table. A ceiling fan hangs above, enhancing airflow. The open layout connects to the dining area visible in the background, offering a seamless flow between spaces.
Home in Palmetto Dunes
5 out of 5 average rating, 4 reviews

Modern Pet Friendly Beach House in Palmetto Dunes

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

Guest favorite
The outdoor area features a private pool with a cozy seating arrangement nearby. A fire pit with glowing embers is central to the setting, surrounded by large loungers and a dining table. A large umbrella shades the outdoor seating, while a whimsical inflatable swan floats in the water.
Home in Sea Pines
5 out of 5 average rating, 15 reviews

Marsh Views | Pool, HotTub, Game Room&Pet Friendly

Guest favorite
A single-story bungalow is presented with a welcoming entryway featuring a partially covered porch. The front door is accented by a circular window, with landscaping featuring palmetto plants and natural stone pathways leading to the entrance.
Home in Sea Pines
4.88 out of 5 average rating, 25 reviews

19 Night Heron,Sea Pines Cottage, 5m walk to beach

Superhost
The great room features a light and airy design, with high ceilings and large windows allowing natural light. Comfortable blue seating is arranged around a central coffee table, while a large flatscreen TV is mounted on an entertainment unit. Decorative accents are displayed on shelves.
Home in Palmetto Dunes
5 out of 5 average rating, 4 reviews

157 Mooring Buoy "The She Shack" - 3b, 3rd Row Pal

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Quick stats about vacation rentals in Hilton Head Island

  • Total rentals

    6.2K properties

  • Nightly prices starting at

    € 9 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.

  • What types of vacation rentals are available in Hilton Head Island?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Hilton Head Island. From over 1,400 house rentals, over 970 villa rentals, over 2,750 condo rentals to over 490 apartment rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • 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.

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