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 - 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, 2.5 BATHSSecond floor villa with stunning viewsOpen living space with hardwood flooringSpacious bedrooms with comfortable beddingClose proximity to pool, shops, dining, and the beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our lovely villa, just steps away from the beautiful ocean and the island s 50 miles
2 BEDS, 2.5 BATHSBeach oriented villa w/ high-quality interior finishesSpacious living area with large windowsShort walk to a beautiful beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your dream vacation home! This beautifully renovated beach oriented villa is the perfect place to unwind and relax. As soon as you st
2 BEDS, 2 BATHSStunning villa in prime location, Palmetto DunesSpacious rooms with comfortable furnishingsPrivate deck overlooking Fazio Golf CourseComplex pool and spacious sundeckXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your newly remodeled vacation home in Hilton Head Island's Palmetto Dunes community. This
2 BEDS, 2 BATHSBeautiful pet friendly villa in Palmetto DunesSoaring ceilings and a spacious great room living areaWrap-around deck with serene viewsExclusive private beach access with three miles of pristine sandXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to this beautifully remodeled vacation home in Hilton Head Islan
3 BEDS, 2.5 BATHSSpacious pet friendly unit in Palmetto DunesUpdated kitchen and cottage-style furnishingsPrivate deck perfect for relaxationShort walk to the beachXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Escape to the beautiful Hilton Head Island and experience the perfect vacation in this spacious and charming 3-bedroom vi
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
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeTastefully decorated first floor villaKing-sized bed in master suite with ocean viewsConvenient access to beach, pool, and all amenitiesXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your dream vacation home at Sea Cloisters on Hilton Head I
1BD, 1.5 BTHSBeautifully renovated villa in Palmetto DunesPerfect beach getaway for couplesWell-equipped kitchenAccess to community poolXplorie - 2 Adult Bikes (Valid for stays between 3-21 nights)Welcome to 1770 St. Andrews in Palmetto Dunes! This beautifully renovated and dog-friendly 1-bedroom, 1.5-bathroom condo is the perfect getaway for
2 BEDS, 2.5 BATHSPet friendly villa perfect for a getawayOpen living space to dining areaFully equipped kitchen ideal for family cookingNestled in the serene and picturesque Shipyard PlantationXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to Tennismaster Villas, a stunning vacation home located in the serene Shipyard Plan
2BR/2BA Villa Charming villa in the heart of ShipyardSpacious living are with plush furnishingsAccess to complex pool and hot tubWalking distance to beaches and bike pathsXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your beautiful vacation home, nestled in the heart of Shipyard Plantation's Colonnade Clu
3 BED, 2.5 BATHSCozy villa ideal for family getawaysOpen floor plan with plenty of room for the whole familyShort stroll away from the pristine beachOnsite pool for refreshing dips and poolside relaxationXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to this wonderful 3-bedroom, 2.5-bathroom villa in Hilton Head Islan
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