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
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
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Villa - Stoney Creek 249, Sea Pines
Condos/Villas
1
bedrooms
1
baths , 1 Half
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
3
bedrooms
3
baths
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
2
bedrooms
2
baths
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
2
bedrooms
2
baths
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
2
bedrooms
2
baths
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
2
bedrooms
2
baths
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
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Villa - Sea Cloisters 203, Folly Field
Condos/Villas
2
bedrooms
2
baths
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
2
bedrooms
2
baths
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
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Villa - Wendover Dunes 8128, Palmetto Dunes
Condos/Villas
2
bedrooms
2
baths , 1 Half
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
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Villa - Windsor Place II 2415, Palmetto Dunes
Villas
1
bedrooms
2
baths
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
2
bedrooms
2
baths
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
4
bedrooms
4
baths
14
guests
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