Hilton Head Summer Rentals, Cottages & Cabins

Book a Place to Stay in Hilton Head for Your Summer Getaway

About Hilton Head Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Hilton Head are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Hilton Head with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Hilton Head Luxury Rentals

There are a lot of options in Hilton Head. If you plan on staying in the Hilton Head area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Hilton Head:

In 2025, PickleTrip offers 10889 summer rentals in or around Hilton Head. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Hilton Head is $481. Check the full list of summer accommodations in Hilton Head.
There are 10889 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

Yes, here are some popular summer holiday rentals in Hilton Head that have a private or indoor pool:

Check all holiday rentals with a pool in Hilton Head on PickleTrip.

Yes, We have 10889 summer rental homes in Hilton Head and types of place to stay in Hilton Head include:

  • Vacation Homes: 10889 available for rent
  • Villas: 10889 Rentals available for rent
  • Holiday Apartments: 10889 Rentals available for rent
  • Hotels with Suites: 10889 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Hilton Head. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Hilton Head.