Hilton Head Island Rentals with Private Pools

Explore our collection of Hilton Head Island vacation rentals with private pools, offering a refreshing place to unwind, gather, and enjoy sunny island days at your own pace. Each home includes comfortable outdoor furnishings, plentiful towels, and pool-safe dishes and drinkware for easy days by the water. 

Every BESTNEST is thoughtfully selected, fully outfitted, and prepared to our consistent standards of comfort, cleanliness, and care. Many private pools may also be heated seasonally; availability, pricing, and guidelines vary by property. Browse the rentals below to find the Nest - and pool - that fit your Hilton Head Island vacation.