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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

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Hilton Head Island vacation rentals

Beachfront
Self check-in
Free parking on premises
Monthly stays
Gym

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
Omni Hilton Head Oceanfront Resort5 locals recommend
Sonesta Resort Hilton Head Island3 locals recommend
The Westin Hilton Head Island Resort & Spa6 locals recommend

Hilton Head Island beach vacation rentals

Guest favorite

Condo in Hilton Head Island

4.85 out of 5 average rating, 233 reviews

Charming Sea Pines Villa with View on Hilton Head

Oct 31 – Nov 7

G$30,382 GYD per night
Guest favorite

Condo in Hilton Head Island

4.95 out of 5 average rating, 225 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo

Dec 19 – 26

G$38,201 GYD per night
Guest favorite

Condo in Hilton Head Island

4.97 out of 5 average rating, 118 reviews

Ocean Overlook - The Ultimate Vacation Experience

Jan 15 – 22

G$48,509 GYD per night
Guest favorite

Condo in Hilton Head Island

4.95 out of 5 average rating, 201 reviews

Cozy Renovated Unit Great Location

Nov 12 – 19

G$26,653 GYD per night
Superhost

Condo in Hilton Head Island

4.84 out of 5 average rating, 105 reviews

AWESOME Retreat! King bed! Ocean View! 2 Bikes 218

Dec 12 – 19

G$36,080 GYD per night
Guest favorite

Villa in Hilton Head Island

4.92 out of 5 average rating, 329 reviews

Direct Ocean Front S. Forest Beach

Feb 15 – 22

G$36,273 GYD per night
Guest favorite

Condo in Hilton Head Island

4.97 out of 5 average rating, 196 reviews

HHBT Resort-OceanView-Remodeled-Steps to beach!

Sep 26 – Oct 3

G$37,791 GYD per night
Guest favorite

Condo in Hilton Head Island

4.88 out of 5 average rating, 113 reviews

Sandy Feet Retreat-New Shower-Steps to the ocean

Oct 12 – 19

G$23,600 GYD per night
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Hilton Head Island house rentals

Guest favorite

Home in Hilton Head Island

4.85 out of 5 average rating, 100 reviews

Palmetto Dunes Home on 1st Tee Fazio Golf Course

Feb 21 – 28

G$103,014 GYD per night
Superhost

Home in Hilton Head Island

4.83 out of 5 average rating, 177 reviews

Park at the Beach - live like a local!

Jul 28 – Aug 4

G$96,097 GYD per night
Guest favorite

Home in Hilton Head Island

4.97 out of 5 average rating, 106 reviews

Lovely 3BR in Palmetto Dunes w/ new pool & spa

Jan 20 – 27

G$103,567 GYD per night
Superhost

Home in Hilton Head Island

4.84 out of 5 average rating, 122 reviews

FREE Heated Pool, Walk to Beach, Elevator, Theater

Sep 7 – 14

G$190,435 GYD per night
Guest favorite

Home in Hilton Head Island

4.85 out of 5 average rating, 163 reviews

Private Beach Access-Pet Friendly-Hot Tub!

Aug 6 – 13

G$234,571 GYD per night
Guest favorite

Home in Savannah

5.0 out of 5 average rating, 392 reviews

Penrose Cottage

Mar 29 – Apr 5

G$32,509 GYD per night
Guest favorite

Home in Hilton Head Island

4.94 out of 5 average rating, 126 reviews

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

Mar 5 – 12

G$207,084 GYD per night
Superhost

Home in Hilton Head Island

4.78 out of 5 average rating, 257 reviews

Nan's Slice of Paradise

Aug 13 – 20

G$38,334 GYD per night
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Hilton Head Island villa rentals

Guest favorite

Villa in Hilton Head Island

4.92 out of 5 average rating, 104 reviews

Spacious Villa with Two King Suites

Sep 1 – 8

G$98,243 GYD per night
Superhost

Villa in Hilton Head Island

4.96 out of 5 average rating, 130 reviews

View on 9th Fairway -Updated Turnberry Villa in PD

Oct 2 – 9

G$53,130 GYD per night
Guest favorite

Villa in Hilton Head Island

4.89 out of 5 average rating, 111 reviews

COMPLETELY REMODELED 3 BR Great Location

Nov 30 – Dec 7

G$62,390 GYD per night
Superhost

Villa in Hilton Head Island

4.89 out of 5 average rating, 160 reviews

Coastal Charm - Beach, pickleball, golf, pets

Nov 15 – 22

G$63,140 GYD per night
Guest favorite

Villa in Hilton Head Island

4.91 out of 5 average rating, 76 reviews

Direct beach access for couple’s getaway!

Nov 17 – 24

G$33,954 GYD per night
Superhost

Villa in Hilton Head Island

4.88 out of 5 average rating, 16 reviews

2BR 4th-floor villa with balcony & beach access

Dec 4 – 11

G$36,114 GYD per night
Guest favorite

Villa in Hilton Head Island

5.0 out of 5 average rating, 34 reviews

Oceanfront Scandi Oasis Amazing View & Heated Pool

Sep 20 – 27

G$89,952 GYD per night
Guest favorite

Villa in Hilton Head Island

4.93 out of 5 average rating, 14 reviews

Beautiful grounds! New Windows!

Nov 5 – 12

G$35,877 GYD per night
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Quick stats about vacation rentals in Hilton Head Island

  • Total rentals

    5.5K properties

  • Rentals with a pool

    4.8K properties have a pool

  • Pet-friendly rentals

    790 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

    G$2,090 GYD 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 20 cottage rentals, over 1,260 house rentals, over 2,350 condo rentals to over 1,060 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 2,590 vacation rentals in Hilton Head Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore