Rentals with a Pool

Whether you're looking for a private pool to relax in your own oasis or a community pool perfect for family fun, our Hilton Head vacation rentals offer the best of both worlds. Cool off after a day at the beach, lounge poolside with a good book, or take an evening dip under the stars—your perfect getaway starts here!


Properties Available 116 properties available
1 BED, 1 BATHNewly renovated villa with modern and upscale furnishingsFully stocked kitchen with stainless steel appliancesShort walk to charming shops, delightful restaurants, and the iconic Harbourtown lighthouseXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to Stoney Creek Villa 249, your ultimate relaxing and comfortab
Villa - Stoney Creek 249, Sea Pines
Condos/Villas Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths , 1 Half
Guests 4 guests
3 BEDS, 3 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeCozy and inviting living area perfect for relaxationPrivate deck breathtaking views of the oceanLocated in the heart of Hilton Head IslandXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your luxurious vacation home in Hilton Head Island,
Villa - Sea Cloisters 506, Folly Field
Condos/Villas
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
2 BEDS, 2 BATHSPet friendly condo with vault ceilingsSpacious living area with comfortable furnishingsDeck that overlooks the George Fazio golf courseAccess to complex pool and tennis courtsXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welcome to your new vacation home! This two-bedroom, two-bathroom condo located in Palmet
Villa - Inverness 949, Palmetto Dunes
Condos/Villas Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
2 BEDS, 2 BATHSPet friendly villa in prime location, Palmetto DunesSpacious living space with hardwood flooringAccess to complex amenities, such as a pool and tennis courtsWalking distance to beach, golf courses, and shopsXplorie - 2 Free Adult Bikes (Valid for stays from 3 -21 nights)Welcome to the Villa at 7830 Centrecourt, your perfect vacation
Villa - Centrecourt 7830, Palmetto Dunes
Condos/Villas Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeStylishly furnished villaSpacious interior exudes elegance and sophisticationExpansive and private oceanfront poolXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to Villa 309, a recently renovated and updated vacation home in Hilton Head Is
Villa - Sea Cloisters 309, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeProfessionally decorated with a luxurious and inviting atmosphereRemodeled kitchen with bar seatingPanoramic ocean views from the living room and balconyXplorie - 2 Free Adult Bikes (Valid for stays in 3 - 21 days) Indulge in the ultimate tropical getaway at this p
Villa - Sea Cloisters 104, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeExtensive villa with ocean viewsSundecks and lush semi-tropical landscapingXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our newly renovated villa, where no expense has been spared to provide you with the very best beach experience. The vil
Villa - Sea Cloisters 203, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeFirst floor unit w/ breathtaking ocean viewsSpacious living room with entertainment optionsOpen kitchen and dining area with bar seatingXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Unit 102 is the epitome of beachfront luxury. As you step inside
Villa - Sea Cloisters 102, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
2 BEDS, 2.5 BATHSCozy coastal villa with maritime forest viewsPrivate suite with a king bed and private bathScreened-in porch for outdoor livingConcishare (Includes access to luxury concierge service)Xplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welcome to Wendover Dunes, the newest ocean-side complex in Palmetto Dunes
Villa - Wendover Dunes 8128, Palmetto Dunes
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths , 1 Half
Guests 6 guests
1BD, 2BTHBuilding Construction from Sep 2024 - April 2025, subject to changeGreat Oceanfront Complex Amenities at Windsor PlaceTwo Large Pools / Spa / Kiddie PoolCovered Pavilion with Gas Grilling AreaPoolside Restrooms with Boardwalk to the OceanThree Golf Courses and World Class Tennis & Pickleball Center in Palmetto DunesXplorie - 2 Adult Bi
Villa - Windsor Place II 2415, Palmetto Dunes
Villas
Bedrooms 1 bedrooms
Bathrooms 2 baths
Guests 4 guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeFully furnished for a hassle-free stayPrivate deck overlooking the oceanProvides a relaxing and peaceful getawayXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your perfect vacation home in Hilton Head Island! This stunning villa offers
Villa - Sea Cloisters 410, Folly Field
Condos/Villas
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
4 BEDS, 4 BATHSVilla offering a relaxing space to unwindBright, open floor plan featuring vaulted ceilingsLoft area providing additional sleeping spaceOffers easy access to the beach and resort amenities.Xplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our two-story, fully furnished Huntington villa located in the fa
Villa - Huntington 7633, Palmetto Dunes
Condos/Villas
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 14 guests

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