Homes With a Private Pool On Hilton Head
If you're dreaming of a luxurious retreat on Hilton Head Island, homes with a private pool offer the ultimate in relaxation and indulgence. Imagine spending your days basking in the warm sunshine, taking refreshing dips in your own secluded oasis, and enjoying the tranquility of your surroundings. With a wide range of stunning properties to choose from, finding the perfect Hilton Head home with a private pool is easier than ever.
Renting a home with a private pool on Hilton Head Island offers a host of benefits beyond just cooling off on hot summer days. It provides a sense of exclusivity and privacy, allowing you to fully unwind and escape the stresses of everyday life. Plus, it's the perfect setting for hosting unforgettable gatherings and creating lasting memories with your loved ones.
All of the homes with private pools managed by Island Time feature the most requested amenities, can be found in great locations on Hilton Head Island, and include access to our Luxury Concierge services. Whether you choose to stay in Sea Pines, Palmetto Dunes, North Forest beach, South Forest Beach or mid-island, you can find the perfect hoes for your next family vacation, or friends getaway. Give us a call at (843) 785-3456 if you need assitance in find a home with a private pool.
67 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home is a stunning haven nestled in the heart of Sea Pines, where luxury meets comfort in a beautiful retreat.
Step inside and feel the warmth of this exquisitely remodeled 18 Willow Oak. Beautiful 8-inch wood flooring guides you through the open layou
18 Willow Oak
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Now Complete, Stunning Outdoor Upgrades!
The beautiful new saltwater heated plunge pool and spacious back deck are now finished and ready for its first guests to enjoy. Updated professional photos of the new outdoor space have now been uploaded so you can soo
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home has been freshly updated with brand new exterior paint, kitchen countertops, renovated bedrooms and bathrooms, a new grill, and more exciting upgrades throughout! Photos have been updated to reflect these updates as of February 2026.
This pet-frien
36 Red Oak
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Indulge in the tranquil charm of a beach vacation at 25 Singleton Beach, a grand and luxurious 7-bedroom retreat designed for unforgettable seaside getaways. This stunning brand-new home boasts large glass doors and windows that flood the interior with natura
25 Singleton Beach
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Perfectly situated within the heart of Palmetto Dunes and just a short stroll from the beach, 3 Cartgate offers the ideal combination of spacious living, thoughtful updates, and relaxed coastal comfort. Recently enhanced with new flooring throughout much of t
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning 5-bedroom, 5.5-bathroom oceanfront home is nestled in the heart of North Forest Beach, offering an unforgettable coastal experience with sweeping views of the Atlantic. As you step through the bright and welcoming entryway, you are immediately
3 Dune Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This Palmetto Dunes beach home features 4 bedrooms and is only a short walk to the beach—that is, if you ever want to leave this gem!
15 Sea Lane features a spacious open floor plan and plenty of natural sunlight! Unwind in the living room as you watch TV on
15 Sea Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Discover the ultimate island retreat in this newly built pet-friendly three-story home, perfectly designed for a relaxing getaway. With its elegant interiors and thoughtfully curated outdoor spaces, this stunning property is an oasis of comfort and style. T
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning home has recently undergone a series of thoughtful updates designed to enhance both comfort and style. A brand new fifth bedroom has been added, now featuring a comfortable queen bed to provide additional sleeping accommodations. The property ha
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautifully renovated 3-bedroom, 2.5-bath home has an open floor plan. The living room has ample room to relax and watch TV on the large flat screen; the dining area seats six people; and the kitchen has stainless steel appliances, granite counters, and
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Nestled within the picturesque surroundings of Palmetto Dunes on Hilton Head Island, South Carolina, this exquisite 5-bedroom house offers the epitome of coastal luxury living. Just a leisurely stroll away from the pristine sandy shores of the beach, this hom
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Located on a quiet street, with Harbour Town Golf Course just steps away, 35 Battery has a light, bright feel and an open, single-level floor plan. Upon entering the front door, a foyer leads guests directly into the living/dining room, which has cathedral ce
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