7,353 Hilton Head Island Holiday Rentals

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Compare Hilton Head Island holiday rentals from 11 rental sites including HomeAway, PerfectPlaces, Booking.com and more, ranging from $25 to $5285 a night.

Information about Hilton Head Island

About Hilton Head Island

Commonly known for its amazing golfing, Hilton Head is also great for tennis, volleyball, polo, and more. The island even hosts many prestigious sporting events throughout the year. With a wide variety of first-class resorts to choose from and 12 miles of pristine beaches, Hilton Head also makes a great vacation. Take a look at the swamp at the Sea Pines Forest Preserve or take a stroll down the boardwalk.

Things to do in Hilton Head Island

Hilton Head boasts 24 world class golf courses and 350 tennis courts. In between matches, enjoy an easy day in the sun on one of the top 10 family beaches in the United States. If you're looking for outdoor adventure, try horseback riding through a forest preserve or biking on the beach or moss-draped trails. Of course, no trip to Hilton Head is complete without trying their famous Lowcountry cuisine. Very similar to New Orleans and Cajun cuisine, Lowcountry cuisine also has a vibrant African cuisine influence and offers a menu full of shrimp, fish, crabs, and oysters.

Day trips from Hilton Head Island

Hilton Head is less than an hour away from Savannah, Georgia, so it's definitely worth a trip across the state line. Savannah is a picturesque southern town with its period architecture, oak-lined streets, and good old southern hospitality. There are plenty of historical sites and museums to explore as well as the supposedly haunted Bonaventure Cemetery. Or, spend the day sipping mint juleps along with fresh seafood and creamy grits! If you'd rather stay stateside, make the trip to Charleston. This historic town is also bursting with Southern charm and hospitality. Take a stroll down Waterfront park while enjoying the view of the Battery and the French Quarter or have a peaceful day at the gardens at Middleton Place.

Hilton Head Island accommodations

Hilton Head offers everything you could possible imagine. Choose to stay at an oceanfront resort where your every need is taken care of, or try a private vacation rental with all the luxuries of home. For a true getaway, stay at the Inn & Club at Harbour Town - Sea Pines Resort. From the second you're met at the grand entrance, your entire stay will be like a dream. For some family-friendly fun, stay at Disney's Hilton Head Island Resort. The resort has a full calendar of activities that the kids will love.

Transportation in Hilton Head Island

Arrive at Hilton Head by flying through the Hilton Head Island Airport or the Savannah/Hilton Head International Airport. There is very little public transportation in Hilton Head, but because the town is so small, you don't even need it! Depending on where you stay, you can easily access everything you need by foot or bike.

Vacation Rentals in Hilton Head Island

Find the best Hilton Head Island vacation rentals with Tripping.com. Choose from 7613 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $5285 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 5576 of homes in Hilton Head Island offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 4893 rentals with pool or jacuzzi, or relax with the family in one of the 5323 homes with cable TV.

For all those dog lovers and cat lovers, Hilton Head Island offers 861 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 11 rental sites in Hilton Head Island where the top providers in that area are HomeAway, PerfectPlaces, and Booking.com. There are 4108 HomeAway rentals, 1208 PerfectPlaces short term rentals and 1140 Booking.com vacation rentals.