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 changeSpacious living areas providing a peaceful and relaxing environmentBreathtaking ocean views from bedroomsEnjoy the private deck with soothing sounds of the oceanXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Welcome to your tastefully d
Villa - Sea Cloisters 412, Folly Field
Condos/Villas
2
bedrooms
2
baths
6
guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeContemporary style villaWell-equipped kitchen with modern appliancesDirect beach access via private walkwayXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to Sea Cloisters Unit 206, a newly renovated vacation villa with stunning panoramic views
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 206, Folly Field
Condos/Villas
2
bedrooms
2
baths
6
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, 2.5 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
Villa - Sandcastle Plaza 2A, Folly Field
Condos/Villas
2
bedrooms
2
baths , 1 Half
8
guests
2 BEDS, 2 BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeProfessionally decorated with a luxurious and inviting atmospherePanoramic ocean views from the living room and balconyExpansive and private oceanfront poolXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights) Indulge in the ultimate tropical getaway at
Villa - Sea Cloisters 403, Folly Field
Condos/Villas
2
bedrooms
2
baths
6
guests
5 BDS, 3.5 BTHSNEW HOME CONSTRUCTION NEXT DOORBreathtaking ocean views and easy beach accessample space for relaxation and entertainmentWell-equipped kitchen with luxurious amenitiesXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to 19 Dune Lane, the perfect oceanfront vacation home for those seeking the ultimate island exp
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.
Home - 19 Dune Lane, Forest Beach
Homes
5
bedrooms
3
baths , 1 Half
13
guests
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
Villa - Courtside 78, Forest Beach
Villas
2
bedrooms
2
baths , 1 Half
6
guests
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
Villa - St Andrews Common 1882, Palmetto Dunes
Condos/Villas
2
bedrooms
2
baths
8
guests
4 Bed / 3 BathSecluded family home locate in Sea PinesSpacious open floor plan with large living roomConvenient location between Harbour Town and the beachLush landscapes, scenic lagoons, and pristine beachesXplorie - 2 Free Adult Bikes (Valid from 3-21 nights)Escape to a gorgeous vacation home in Sea Pines, where luxury and comfort meet. This stun
Home - 11 Hollyberry Lane, Sea Pines
Homes
4
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, 2BATHSBuilding Construction from Sep 2024 - May 2025, subject to changeExquisite condominium with fresh, coastal decorationsOpen concept living and dining areaExpansive and private oceanfront poolXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to our beautiful vacation home in Hilton Head, SC! This exquisite two-bed
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 302, Folly Field
Condos/Villas
2
bedrooms
2
baths
4
guests
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
Villa - Stones Throw 26, Folly Field
Condos/Villas
3
bedrooms
2
baths , 1 Half
8
guests
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