Hilton Head Vacation Rentals with Private Pools
Experience the ultimate Hilton Head getaway with a vacation rental that features a private pool. At Hilton Head Properties, we offer a selection of stunning homes and villas where you can relax, unwind, and enjoy the perfect blend of comfort and convenience
16 properties available
4 BEDS/ 3.5 BATHSDog friendly home located in Sea PinesSpacious living room, dining room, and kitchenLarge outdoor pool and screened-in porchShort walk to the beachXplorie (Valid for stays from 3 - 21 nights)Looking for a prime location for your next vacation? Look no further than 16 Duck Hawk, located in the heart of Sea Pines on Hilton Head Islan
4 BEDS, 3 BATHSFamily friendly home perfect for kids and dogsPlenty of room for relaxation and entertainmentGame room perfect for family fun and game nightsShort walk to the beach and close to amenitiesXplorie - 2 Free Adult Bikes (Valid for stays between 3 - 21 nights)Walk up the street just 2 short blocks (3 minutes) to expansive North Forest Bea
4 BEDS / 4.5 BATHSTastefully decorated family home in Sea PinesSpacious living area with open layoutExpansive patio with private pool and spaXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to your luxurious vacation retreat nestled in prestigious Sea Pines. This exquisite vacation home offers the perfect blend of elegance,
5 BEDS / 4 BATHSOceanfront home in Sea Pines w/ breathtaking viewsSpacious and stylish accommodationsSpacious outdoor area with private pool, spa, and outdoor kitchenXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Welcome to 33 Ruddy Turnstone, an exceptional oceanfront vacation home located in the prestigious Sea Pines resort of H
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
4BD, 4BTH,Large home perfect for a family getawayPrivate Pool & SpaWalking distance to the beachXplorie - 2 Adult Bikes (Valid 3 - 21 stays)Brand New in Fall 2024! Your Beachside Oasis in Folly FieldWelcome to your dream getaway—a stunning, purpose-designed 4-bedroom beachside home in the heart of Hilton Head Island's beloved Folly Fi
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
5 BD, 5BTHs****** UNDER CONSTRUCTION - Estimated Completion Date 12/25**********Newly Renovated Family Home in Sea PinesPrivate Pool & Spa (Heat Option w/ additional fee)Spacious living area w/ comfortable furnishingXplorie - 2 Adult Bikes (Valid for 3-21 night staysWelcome to 9 Fern Court, the perfect vacation home for those seeking a serene a
4 BEDS | 4 BATHSNewly constructed family home in Palmetto DunesSpacious great room with vaulted ceilingsUpstairs rec room with double-sized bunk bedsClose to bike paths, nature trails, and dining/shopping optionsXplorie: 2 Adult Bikes (Valid for stays from 3 to 21 nights) Welcome to your dream vacation home at 16 Cartgate in Palmetto Dunes, Hi
4BR/4BABeautiful family home in prime locationSpacious and inviting living spaceGame room perfect for family funXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Experience the ultimate beach vacation at this 4-bedroom getaway with an open layout and stunning golf course views. Just a few minutes bike or walk via bike pathways to the
6BR / 6.5BASpacious family home in prime locationLarge rooms with comfortable accommodationsPrivate pool perfect to relax and unwindClose proximity to the oceanXplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)This stunning new 2020 beach home is perfect for families looking for a memorable vacation. With six spacious bedrooms and to
7 BDS / 6.5 BTHSSpacious home perfect for a family getawayLarge private pool with diving boardSpacious game room Xplorie - 2 Free Adult Bikes (Valid for stays from 3 - 21 nights)Looking for a vacation home that offers something for everyone in the family? Look no further than 25 Starboard Tack in Palmetto Dunes. This stunning home boasts spaci
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