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Hilton Head Island vacations

Find the best Hilton Head Island flights, deals, all-inclusive resorts and vacation packages at Southwest Vacations. Book your trip and save today.

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Here are a few of our most popular Hilton Head Island resorts:

  • Main

    Hilton Head

    The Westin Hilton Head Island Resort & Spa

    Westin Hilton Head Island is nestled along the beach in Port Royal Plantation.

  • Exter

    Hilton Head Island via Charleston

    Hilton Head Island Beach and Tennis Resort

    The ultimate destination for a fun-filled family vacation or a relaxing getaway for two.

  • Exterior

    Hilton Head Island via Charleston

    Studios at the Village at Palmetto Dunes

    This small community is situated between the tennis center and the Trent Jones golf course.

Things to do in Hilton Head Island, SC

  • Daufuski beach & trail rides

    Enjoy a once-in-a-lifetime experience horseback riding on the beach in Hilton Head Island. 
  • Exceptional Golf Courses

    Hilton Head Island is an amazing place to plan your golf getway. With over 33 world-class golg courses in the Lowcountry area. Home to PGA Tour events and courses artitechted by legends like Jack Nicklaus. From novice to experienced golfers, Hilton Head Island ensures a great time on the course!
  • Shopping on Hilton Head Island

    When vacationing on one of Americ's favorite islands, browse some of Hilton Head Islands wonderful boutiques for amazing treasures, gifts and Lowcountry fair. Find everything you need from local antique shops to island consignment shops. 

Family Activities to do in Hilton Head Island, SC

  • The sandbox: Interactive Children's Museum

    The Sandbox provides an amazing experience with educational play for the whole family. Let your family get capitvated with fun filled activities. 
  • Guided Tours

    Enjoy charming walking tours to explore the areas history or immerse yourself in the Gullah culteral tours to dolphin & seas turtle touches in Hilton Head Island. Whether you are looking for history or fun in the sun, there are tours for everyone to experiences.
  • Explore Lowcountry Waters

    From exploring the vanishing island, setting sail for a sunset cruises to amazing watersports like jetskiing or canoeing Hilton Head Island has experiences for the whole family to enjoy.

Nightlife & Entertainment in Hilton Head Island, SC

  • Rooftop Bar at Poseidon

    Enjoy live music, entertainment and wonderful sunset views on the rooftop at one of Hilton Head's favorite nightlife spots. 
  • Fine Dining

    Dock up for some great seafood or dine by candelight in one of Hilton Head Island's amazing establishments. With over 250 restaurants to choose from, the island has someting for everyone. Check out Red Fish, Brickyard Pub, Truffles Market & Cafe and many more for great cuisine. 
  • Nightlife & Dancing

    Start with a gorgeous sunset to start your nightlife off right as the night has just begin. Enjoy a night of great food, dancing and even comedy at many beachfront establishments in Hilton Head Island. 

Sports enthusiasts, beach-goers, and everyone in between will find plenty of fun at Hilton Head Island. Home to some of the best golf courses in the country, Hilton Head is a world-famous destination for anyone looking for the challenge and beauty of this destination's championship courses. When you finish up your morning round of golf, head to some of Hilton Head's stunning natural attractions. The Sea Pines Forest Preserve will give you an up-close look at the South Carolina swamp from the wonderful vantage point of a raised boardwalk. Enjoy over 12 miles of beaches and catch a glimpse of Hilton Head's iconic Harbour Town Lighthouse. Enjoy outdoor adventures in Hilton Head with a Southwest Vacations® package.

Please note: flight service for Hilton Head Island vacations is into Charleston, South Carolina.