Hilton Head Island Summer Rentals, Cottages & Cabins

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

About Hilton Head Island Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Hilton Head Island 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 Island 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 Island Luxury Rentals

There are a lot of options in Hilton Head Island. If you plan on staying in the Hilton Head Island 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 Island:

In 2025, PickleTrip offers 10229 summer rentals in or around Hilton Head Island. 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 Island is $441. Check the full list of summer accommodations in Hilton Head Island.
There are 10229 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 Island that have a private or indoor pool:

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

Yes, We have 10229 summer rental homes in Hilton Head Island and types of place to stay in Hilton Head Island include:

  • Vacation Homes: 10229 available for rent
  • Villas: 10229 Rentals available for rent
  • Holiday Apartments: 10229 Rentals available for rent
  • Hotels with Suites: 10229 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Hilton Head Island. 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 Island.