Hilton Head Island vacation rentals

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Popular amenities for Hilton Head Island vacation rentals

Stay near Hilton Head Island's top sights

Coligny Beach Park116 locals recommend
Coligny Plaza Shopping Center179 locals recommend
Hilton Head Island Beach & Tennis Resort10 locals recommend
Sonesta Resort Hilton Head Island3 locals recommend
The Westin Hilton Head Island Resort & Spa6 locals recommend
Omni Hilton Head Oceanfront Resort5 locals recommend

Hilton Head Island beach vacation rentals

Guest favorite
Condo in Hilton Head Island
AWESOME Retreat! King bed! Ocean View! 2 Bikes 218
Dec 14 – 21
$153 per night
4.83 out of 5 average rating, 103 reviews
Guest favorite
Condo in Hilton Head Island
Oceanfront Designer! KING BED 65"TV Bar Tennis GYM
Jun 14 – 21
$490 per night
4.97 out of 5 average rating, 214 reviews
Guest favorite
Condo in Hilton Head Island
Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa
Feb 3 – 10
$130 per night
4.97 out of 5 average rating, 151 reviews
Guest favorite
Condo in Hilton Head Island
My Blue Heaven, Romantic Couples Ocean Front View
Aug 29 – Sep 5
$262 per night
4.97 out of 5 average rating, 111 reviews
Guest favorite
Condo in Hilton Head Island
Charming Sea Pines Villa with View on Hilton Head
Aug 20 – 27
$126 per night
4.85 out of 5 average rating, 231 reviews
Guest favorite
Home in Hilton Head Island
Lovely 3BR in Palmetto Dunes w/ new pool & spa
Apr 27 – May 4
$479 per night
4.97 out of 5 average rating, 105 reviews
Guest favorite
Condo in Hilton Head Island
Cozy Renovated Unit Great Location
Oct 28 – Nov 4
$110 per night
4.95 out of 5 average rating, 197 reviews
Guest favorite
Townhouse in Hilton Head Island
Stylish Tennis-Golf- Beach Retreat-Renovated!
Dec 2 – 9
$207 per night
4.91 out of 5 average rating, 166 reviews

Private Hilton Head Island vacation rentals

Guest favorite
Guesthouse in Bluffton
Bluffton's Tropical Carriage House Getaway
$85 per night
4.97 out of 5 average rating, 674 reviews
Guest favorite
Condo in Hilton Head Island
Beachfront property with ocean/sunrise view!
Jan 28 – Feb 4
$129 per night
4.89 out of 5 average rating, 149 reviews
Guest favorite
Condo in Hilton Head Island
Beach&Tennis, Stylish, Modern, Folly Field Beach!
Dec 28 – Jan 4
$134 per night
4.96 out of 5 average rating, 112 reviews
Guest favorite
Condo in Hilton Head Island
Beach resort, pools, tennis, pickle ball, tiki bar
Feb 5 – 12
$149 per night
4.93 out of 5 average rating, 104 reviews
Guest favorite
Condo in Hilton Head Island
2nd row ocean - walk to beach and Salty Dog Cafe
Nov 16 – 23
$153 per night
4.95 out of 5 average rating, 114 reviews
Guest favorite
Apartment in Hilton Head Island
Jim's Stunning Direct Ocean Front 2BR Villa
Feb 19 – 26
$248 per night
4.82 out of 5 average rating, 131 reviews
Guest favorite
Cottage in Hilton Head Island
Gypsy Sea Cottage - A Seaside Retreat
Nov 10 – 17
$140 per night
4.87 out of 5 average rating, 297 reviews
Guest favorite
Condo in Hilton Head Island
Hilton Head Beach & Tennis Resort Ocean View!
Nov 11 – 18
$206 per night
4.92 out of 5 average rating, 212 reviews

Hilton Head Island house rentals

Superhost
Home in Hilton Head Island
Sycamore at the Sound — live like a local!
Dec 25 – Jan 1
$249 per night
4.86 out of 5 average rating, 111 reviews
Superhost
Home in Hilton Head Island
FREE Heated Pool, Walk to Beach, Elevator, Grill
Dec 9 – 16
$400 per night
4.91 out of 5 average rating, 103 reviews
Guest favorite
Home in Hilton Head Island
Modern Waterview Ranch - 3 Bdrm, Walk to Beach
Oct 25 – Nov 1
$332 per night
4.96 out of 5 average rating, 120 reviews
Guest favorite
Home in Hilton Head Island
Peaceful Harbour Town Treehouse with Marsh Views
Apr 9 – 16
$298 per night
4.96 out of 5 average rating, 119 reviews
Guest favorite
Home in Bluffton
Old Town Bluffton Cottage - Includes Golf Cart!
Sep 5 – 12
$298 per night
4.98 out of 5 average rating, 116 reviews
Guest favorite
Home in Hilton Head Island
Hot Tub/Fully Screened Heated Pool/Elevator/Fenced
Jan 10 – 17
$609 per night
4.93 out of 5 average rating, 160 reviews
Guest favorite
Home in Tybee Island
47 Steps to the Beach - Hot Tub Ocean Views!
Oct 26 – Nov 2
$431 per night
5.0 out of 5 average rating, 182 reviews
Guest favorite
Home in Hilton Head Island
Blue Sky Villa: Beach/pets/golf/tennis/pickleball
Dec 2 – 9
$243 per night
4.86 out of 5 average rating, 100 reviews

Quick stats about vacation rentals in Hilton Head Island

Total rentals

5.6K properties

Rentals with a pool

4.9K properties have a pool

Pet-friendly rentals

730 properties allow pets

Family-friendly rentals

4.6K properties are a good fit for families

Total number of reviews

110K reviews

Nightly prices starting at

$10 before taxes and fees

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 2,360 condo rentals, over 1,220 villa rentals to over 1,180 house 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 2,530 vacation rentals in Hilton Head Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

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