Hilton Head Island vacation rentals

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Top-rated vacation rentals in Hilton Head Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Condo in Hilton Head Island

4.93 out of 5 average rating, 162 reviews

Hilton Head BIKE 'n BED - Perfect Couple's Getaway

Come relax and enjoy Hilton Head on South Forest Beach, the most popular section of the island. Ride our free bikes for a quick trip to Coligny Plaza where the quaint local shops and restaurants are. The beach is a quick 2 or less minute walk and the pool is just down the hall. Our condo is small, but perfect for a couple's getaway or a memorable trip with the kids. We have everything you need to help make yourselves at home with full size kitchen appliances and washer/dryer room just next door.

Dec 23 – 30

G$24,550 GYD per night
Superhost

Condo in Hilton Head Island

4.88 out of 5 average rating, 157 reviews

Hilton Head Hidden Gem

Comfy 3rd floor walk up retreat. Peaceful decor. Screened balcony. Furnished kitchen. Free use of WIFI, beach chairs/umbrella, gym, basketball & tennis courts, charcoal grills/picnic tables; pools. Steps from your door: explore our sandy beach, watch fish jump & dolphins swim; observe nature on a private pier. See the sunrise on the water. Grocery/restaurants w/in 1-5 miles. Make a meal or a reservation! Short drive to all island locales. Great island bike paths. (No pets or smoking.)

Dec 9 – 16

G$24,380 GYD per night
Superhost

Condo in Hilton Head Island

4.81 out of 5 average rating, 107 reviews

HILTON HEAD RESORT CONDO - NEWLY RENOVATED

NEWLY RENOVATED condo near the beach! Ready for a relaxing time away? This newly renovated condo is tucked away in the lovely Hilton Head Resort - a gated community w/ 24 hr security, perfect for families who want to create lasting memories at the beach! The resort has everything you need - indoor/outdoor pools, sauna, spa, fitness room, tennis/pickle ball courts, and a private boardwalk to the beautiful beach. Within just a few miles are grocery stores, restaurants, shopping centers, and more!

Oct 28 – Nov 4

G$26,346 GYD per night

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

Hilton Head Island beach vacation rentals

Guest favorite

Villa in Hilton Head Island

4.92 out of 5 average rating, 329 reviews

Direct Ocean Front S. Forest Beach

Feb 25 – Mar 4

G$36,516 GYD per night
Guest favorite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 271 reviews

LOCATION! Harbour, Dining, Shops, Beach-1.4 mile

Jul 4 – 11

G$32,661 GYD per night
Guest favorite

Condo in Hilton Head Island

4.97 out of 5 average rating, 205 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Dec 1 – 8

G$31,713 GYD per night
Guest favorite

Condo in Tybee Island

4.93 out of 5 average rating, 516 reviews

Adorable Beachfront Condo

Jan 25 – Feb 1

G$21,583 GYD per night
Guest favorite

Condo in Hilton Head Island

4.93 out of 5 average rating, 105 reviews

Spacious Two Bedroom Villa in Hilton Head Resort!

Oct 27 – Nov 3

G$29,539 GYD per night
Guest favorite

Condo in Hilton Head Island

4.89 out of 5 average rating, 149 reviews

Beachfront property with ocean/sunrise view!

Feb 22 – Mar 1

G$31,246 GYD per night
Superhost

Cottage in Hilton Head Island

4.87 out of 5 average rating, 297 reviews

Gypsy Sea Cottage - A Seaside Retreat

Dec 13 – 20

G$32,081 GYD per night
Guest favorite

Condo in Hilton Head Island

4.83 out of 5 average rating, 132 reviews

1st Floor Condo, Just Steps away from the Beach!

Sep 5 – 12

G$28,611 GYD per night
Guest favorite

Condo in Hilton Head Island

4.97 out of 5 average rating, 216 reviews

Oceanfront Designer! KING BED 65"TV Bar Tennis GYM

Aug 10 – 17

G$114,231 GYD per night
Guest favorite

Condo in Hilton Head Island

4.91 out of 5 average rating, 442 reviews

(4) Location! Walk to Coligny Beach Shops Dining!

Feb 25 – Mar 4

G$35,103 GYD per night
Superhost

Condo in Hilton Head Island

4.79 out of 5 average rating, 123 reviews

After Dune Delight Beach Condo, Hot Tub/Pickleball

Apr 20 – 25

G$33,468 GYD per night
Guest favorite

Condo in Hilton Head Island

4.94 out of 5 average rating, 144 reviews

HHI Beach Villa | Getaway | Indoor Pool & Hot Tub

Apr 6 – 13

G$29,780 GYD per night

Hilton Head Island house rentals

Guest favorite

Home in Hilton Head Island

4.97 out of 5 average rating, 105 reviews

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

Jan 12 – 19

G$103,775 GYD per night
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

Dec 10 – 17

G$103,221 GYD per night
Superhost

Home in Hilton Head Island

4.84 out of 5 average rating, 159 reviews

Private Beach Access-Pet Friendly-Hot Tub!

Aug 27 – Sep 3

G$188,734 GYD per night
Guest favorite

Home in Hilton Head Island

4.96 out of 5 average rating, 119 reviews

Peaceful Harbour Town Treehouse with Marsh Views

Aug 13 – 20

G$64,939 GYD per night
Guest favorite

Home in Hilton Head Island

4.93 out of 5 average rating, 123 reviews

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

Jan 29 – Feb 5

G$104,156 GYD per night
Superhost

Home in Hilton Head Island

4.86 out of 5 average rating, 113 reviews

Sycamore at the Sound — live like a local!

Apr 26 – May 3

G$72,607 GYD per night
Guest favorite

Home in Tybee Island

5.0 out of 5 average rating, 183 reviews

47 Steps to the Beach - Hot Tub Ocean Views!

Dec 19 – 26

G$78,291 GYD per night
Guest favorite

Home in Hilton Head Island

4.96 out of 5 average rating, 120 reviews

Modern Waterview Ranch - 3 Bdrm, Walk to Beach

Aug 1 – 8

G$92,741 GYD per night
Superhost

Home in Hilton Head Island

4.91 out of 5 average rating, 103 reviews

Luxe & Fun Family Gem ~ Walk to Beach ~ Pool ~ BBQ

Feb 8 – 15

G$117,547 GYD per night
Guest favorite

Home in Bluffton

4.98 out of 5 average rating, 118 reviews

Old Town Bluffton Cottage - Includes Golf Cart!

Oct 14 – 21

G$71,828 GYD per night
Guest favorite

Home in Bluffton

4.99 out of 5 average rating, 339 reviews

Bluffton Farm Cottage: Experience Southern Charm

Aug 18 – 25

G$66,904 GYD per night
Superhost

Home in Bluffton

4.88 out of 5 average rating, 170 reviews

Bluffton/Hilton Head Island/Savannah Vacation Home

Feb 23 – Mar 2

G$36,564 GYD per night

Private Hilton Head Island vacation rentals

Guest favorite

Condo in Hilton Head Island

4.92 out of 5 average rating, 116 reviews

Spring Rates! 2 Queen Beds/Indoor Pools/Pickleball

Sep 10 – 17

G$24,247 GYD per night
Guest favorite

Townhouse in Bluffton

4.97 out of 5 average rating, 144 reviews

Newly Remodeled Lowcountry Escape!

Dec 14 – 21

G$26,378 GYD per night
Guest favorite

Guesthouse in Bluffton

5.0 out of 5 average rating, 254 reviews

Bluffton Casita

Jun 5 – 12

G$31,871 GYD per night
Guest favorite

Apartment in Bluffton

4.92 out of 5 average rating, 104 reviews

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

Oct 14 – 21

G$30,206 GYD per night
Guest favorite

Apartment in Bluffton

4.85 out of 5 average rating, 123 reviews

Best of Bluffton

Oct 22 – 29

G$18,807 GYD per night
Guest favorite

Condo in Hilton Head Island

4.85 out of 5 average rating, 150 reviews

Boardwalk to Beach, Hot Tub, 3 Pools and Tennis!

Nov 30 – Dec 7

G$28,174 GYD per night
Guest favorite

Townhouse in Hilton Head Island

4.89 out of 5 average rating, 140 reviews

Relax at Latitude Adjustment!

Sep 3 – 10

G$31,612 GYD per night
Guest favorite

Guesthouse in Bluffton

4.96 out of 5 average rating, 320 reviews

Old Town Bluffton Carriage Apt.

Dec 16 – 23

G$26,736 GYD per night
Guest favorite

Condo in Hilton Head Island

4.85 out of 5 average rating, 150 reviews

Pineapple Paradise

Oct 7 – 14

G$30,443 GYD per night
Guest favorite

Apartment in Bluffton

4.99 out of 5 average rating, 345 reviews

Guest House on Lawrence Street

Dec 11 – 18

G$30,165 GYD per night
Guest favorite

Condo in Hilton Head Island

4.9 out of 5 average rating, 106 reviews

South Forest Beach: First Floor Condo

Mar 14 – 21

G$31,697 GYD per night
Guest favorite

Condo in Hilton Head Island

4.84 out of 5 average rating, 221 reviews

The Beachscape Villa

Feb 22 – Mar 1

G$34,472 GYD per night

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

G$2,094 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 2,360 condo rentals, over 1,180 house rentals to over 1,220 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 2,530 vacation rentals in Hilton Head Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore