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!
116 properties available
2 Beds, 2 BathsBuilding Construction from Sep 2024 - April 2025, subject to changeFifth floor villa located in Palmetto DunesBreathtaking ocean views from the living room and balconyKitchen with a raised countertop barConcishare (Includes access to luxury concierge service)Xplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welco
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
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeTastefully decorated villa with a beach themeOpen floor plan for a spacious feelPrivate patio with stunning ocean viewsSundecks and lush semi-tropical landscapingXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your perfect beach getaway in Hi
2 BEDS, 2 BATHSVilla with comfortable and inviting atmosphereLocated in the renowned Palmetto Dunes ResortSunken living area with a large flat-screen TVPrivate beach access at various locations within the resortXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our St. Andrews Commons vacation home, located in the renowned
7 Beds / 5.5 BathsGourmet kitchen with European appliancesStunning backyard with a huge private pool, covered spa, outdoor kitchen, and fireplaceSeparate guest house with bunk beds and half-bathClose proximity to Forest Beach's beautiful shores and amenitiesXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Looking for a vacation
2 BEDS, 2 BATHSLocated in the sought-after Deer Island community by HarbourtownSpacious and inviting common areas Enjoy the serene beauty of the surrounding landscapeEasy access to shops, restaurants, and golf coursesXplorie - 2 Free Adult Bikes (Valid for stays from 3-21 days)Discover the ultimate retreat at our luxurious 2-bedroom, 2-bathroo
1BD, 2BTHGreat 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 Bikes (Valid for 3 - 21 night stays)Welcome to 2415 Windsor II in Pal
3 BEDS, 3 BATHSLuxurious villa located in Palmetto DunesSpacious, comfortable bedrooms with cozy beddingPrivate balcony with ocean viewsClose to bike paths, shops, dining, and the beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our brand new vacation rental villa, which has been completely remodeled in 2020-2021! Ou
2 BEDS, 2 BATHSSecond floor unit located in Sea PinesOpen, spacious living area with natural lightingSpacious bedroom with cozy bedsClose proximity to Harbourtown shopsXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Introducing 2379 Lighthouse Villa! This exception villa is an end unit overlooking big sweeping lagoon views an
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
2 BD, 2BTHOceanfront luxury villaRelaxing coastal ambianceBreathtaking views from private balconyXplorie - 2 Adult Bikes (Valid for 3-21 night stays)Discover the ultimate in beachfront elegance with this stunning 2-bedroom villa in Hampton Place, Palmetto Dunes on Hilton Head Island. Designed with a coastal chic aesthetic, this villa seamlessly ble
4 BEDS, 3 BATHSFamily-friendly villa in Palmetto DunesIdeal for family vacations, golf outings, and weekend getaways.Private patio with a gas grillShort walk to the beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Escape to your dream vacation home in Palmetto Dunes Resort, where luxury, comfort, and endless fun meet. This beau
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