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
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 - Windsor Place II 2513, Palmetto Dunes
Condos/Villas
2
bedrooms
2
baths
8
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 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
Villa - Sea Cloisters 310, Folly Field
Condos/Villas
2
bedrooms
2
baths
6
guests
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
Villa - St Andrews Common 1677, Palmetto Dunes
Condos/Villas
2
bedrooms
2
baths
6
guests
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
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.
Home - 16 Mallard, Forest Beach
Homes
7
bedrooms
5
baths , 1 Half
22
guests
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
Home - 2030 Deer Island, Sea Pines
Homes
2
bedrooms
2
baths
6
guests
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
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
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
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 - Hampton Place 6108, Palmetto Dunes
Condos/Villas
3
bedrooms
3
baths
8
guests
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
Villa - Lighthouse Tennis Villa 2379, Sea Pines
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 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
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 - Hampton Place 5102, Palmetto Dunes
Villas
2
bedrooms
2
baths
4
guests
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
Villa - Inverness 975, Palmetto Dunes
Condos/Villas
4
bedrooms
3
baths
10
guests
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