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Hilton Head Island vacation rentals

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Hilton Head Island vacation rentals

Self check-in
Beachfront
Free parking on premises
Monthly stays
Pet friendly

Stay near Hilton Head Island's top sights

Hilton Head Island Beach & Tennis Resort10 locals recommend
Folly Field Beach27 locals recommend
Hilton Head Resort6 locals recommend
Palmetto Dunes Oceanfront Resort3 locals recommend
Hudson's Seafood House On The Docks182 locals recommend
Coligny Plaza Shopping Center178 locals recommend

Hilton Head Island beach vacation rentals

Guest favorite

Condo in Hilton Head Island

4.86 out of 5 average rating, 117 reviews

Cozy Two Bedroom Beach Condo

Guest favorite

Condo in Hilton Head Island

4.86 out of 5 average rating, 136 reviews

Beach Resort, pools, tennis, pickle ball Tiki bar!

Guest favorite

Condo in Hilton Head Island

4.87 out of 5 average rating, 119 reviews

Ocean view villa south end with resort amenities

Guest favorite

Condo in Hilton Head Island

4.94 out of 5 average rating, 106 reviews

Ocean View with Beach Access

Guest favorite

Cottage in Hilton Head Island

4.95 out of 5 average rating, 165 reviews

Cozy Cottage 3 Min beach walk-Coligny -Snowbirds

Superhost

Condo in Hilton Head Island

4.8 out of 5 average rating, 227 reviews

Pool side condo just steps from beach boardwalk!

Guest favorite

Guest suite in Tybee Island

4.92 out of 5 average rating, 179 reviews

Searenity Beach Front

Guest favorite

Condo in Hilton Head Island

4.9 out of 5 average rating, 94 reviews

Cozy 1 bed/bath condo steps from natural beach

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Private Hilton Head Island vacation rentals

Superhost

Condo in Hilton Head Island

5 out of 5 average rating, 4 reviews

Luxury Two Bedroom! Marriott Grande Ocean resort!

Guest favorite

Condo in Hilton Head Island

4.83 out of 5 average rating, 24 reviews

Ocean Dunes Villas 111 Ocean View Heated Pool

Superhost

Townhouse in Hilton Head Island

4.71 out of 5 average rating, 7 reviews

Beautiful Island Villa with a lagoon view

Superhost

Condo in Hilton Head Island

4.64 out of 5 average rating, 67 reviews

Mermaids Beach Villa

Guest favorite

Home in Bluffton

4.96 out of 5 average rating, 89 reviews

Cozy 4 bedroom Home in the heart of Old Town with

Guest favorite

Home in Hilton Head Island

4.99 out of 5 average rating, 98 reviews

“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops

Guest favorite

Home in Hilton Head Island

4.94 out of 5 average rating, 139 reviews

Screened Heated Pool/Spa/Elevator/Fenced Yard-79

Superhost

Condo in Hilton Head Island

4.84 out of 5 average rating, 50 reviews

Need a break from ordinary? Relaxing quite Resort

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Hilton Head Island fishing vacation rentals

Guest favorite

Cottage in Tybee Island

4.98 out of 5 average rating, 110 reviews

Couples Retreat FREE Golf Cart/Bikes/Kayaks + Dock

Guest favorite

Rental unit in Bluffton

4.99 out of 5 average rating, 145 reviews

May River Cottage on Lawrence street, old Town.

Guest favorite

Home in Bluffton

4.99 out of 5 average rating, 204 reviews

Old Town Bluffton Home + Golf Cart No Cleaning Fee

Superhost

Condo in Hilton Head Island

4.85 out of 5 average rating, 165 reviews

Family & Kiddo FUN beach resort villa/Hilton Head

Guest favorite

Rental unit in Bluffton

4.92 out of 5 average rating, 146 reviews

One Bed Carriage Hse, Winnie's Corner in Old Town.

Guest favorite

Townhouse in Hilton Head Island

4.97 out of 5 average rating, 122 reviews

Beach Resort Luxe 2b Golf & Lagoon View Pickleball

Guest favorite

Home in Savannah

4.99 out of 5 average rating, 112 reviews

Modern Island Home: Minutes to DT Savannah/Tybee.

Guest favorite

Home in Hilton Head Island

4.87 out of 5 average rating, 117 reviews

Blue Sky Villa: Beach/pets/golf/tennis/pickleball

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Quick stats about vacation rentals in Hilton Head Island

  • Total rentals

    5.9K properties

  • Nightly prices starting at

    $10 before taxes and fees

  • Total number of reviews

    129K reviews

  • Family-friendly rentals

    4.8K properties are a good fit for families

  • Pet-friendly rentals

    890 properties allow pets

  • Rentals with a pool

    5.2K 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 1,350 house rentals, over 2,600 condo rentals to over 990 villa 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 2,710 vacation rentals in Hilton Head Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

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