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5,719 Hilton Head Island Holiday Rentals

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Compare Hilton Head Island holiday rentals from 13 rental sites including HomeAway, Booking.com, PerfectPlaces and more, from $25 a night.

Hilton Head Island Information

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

Looking for the perfect vacation rental for your Hilton Head Island getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Hilton Head Island offers 5719 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 5061 properties with high-speed WiFi Internet, 4410 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget.

For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $7348 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Hilton Head Island has 5719 gorgeous homes with 688 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

Search properties from 13 vacation rental sites in Hilton Head Island where the top providers in that area are HomeAway, Booking.com, and PerfectPlaces. There are 3479 HomeAway rentals, 696 Booking.com short term rentals and 610 PerfectPlaces vacation rentals.