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.




Properties Available 66 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Elegance is understated in this Lowcountry home, truly one of a kind. The setting could not get more perfect. This fabulous home offers 4 bedrooms, 2 master suites, 2 queen bedrooms, and a bunk room. The home boasts multiple living areas on the inside, a gour
Hot HOT 56
51 Haul Away Fairway Collection Icon
House -
$461.00 - $1,164.00 / per night
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 (10)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 5 Rice Lane is a renovated Sea Pines home with a private pool. This coastal home is perfect for vacationing. Be welcomed in by the living room, where you can relax and watch television or unwind with a great book. Heading through the home, the kitchen has amp
5 Rice Lane
House - Pet Friendly
$196.00 - $508.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (3)
Welcome to The Sandbox! Newly renovated and outlined with elegance in every detail, this 3-story oceanfront home is truly perfect for your next Hilton Head Island family getaway. This home has an extremely open floor plan that allows an easy flow between the living room, kitchen, and dining area. The living room is well-appointed and spacious, an
Hot HOT 71
9 Guscio Way Icone Collection Icon
House -
$1,199.00 - $3,000.00 / per night
Bedrooms 8 bedrooms
Bathrooms 8 baths
Guests 20 guests
Rating 5 (17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Your perfect retreat for relaxation and adventure! Whether you\'re here to unwind with family, explore the surrounding area, or simply enjoy time together, this spacious and beautifully designed home is the ideal place to create unforgettable memories. Get re
Hot HOT 53
32 Full Sweep Fairway Collection Icon
House
$383.00 - $1,314.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathrooms 2 half baths
Guests 14 guests
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Nestled in the heart of North Forest Beach, 5 Mallard Road is a charming two-story, four-bedroom home designed for the ultimate coastal retreat. Just a short stroll from the shoreline, this beautifully appointed getaway blends comfort, style, and convenience
New Property New Property
New Property
5 Mallard Road
House
$528.00 - $1,192.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 8 guests
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This beautifully updated 5-bedroom, 4-bath home with a 2-car garage, elevator, and private pool is located at Singleton By The Beach. This home is located by the beautiful Chaplin Park, which offers free tennis, pickleball, basketball courts, and walking trai
28 Corine Lane
House - Pet Friendly
$308.00 - $875.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 15 guests
Rating 4.8 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Step into coastal luxury with this beautiful second-row ocean home, where traditional Carolina charm meets modern elegance for an unforgettable beach getaway. Just steps from a serene semi-private beach, this spacious property is designed to maximize both com
New Property New Property
New Property
19 Sand Dollar
House -
$607.00 - $1,854.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 18 guests
Rating 5 (1)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. The property is situated among the palmettos and oak trees of Hilton Head Island and steps away from the Atlantic Ocean. The lapping of the waves on the beach of this oceanfront home will put you to sleep, while the bedrooms on the street side of the house ge
Hot HOT 55
25 South Beach Lagoon
House -
$1,246.00 - $2,967.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 21 guests
Rating 5 (6)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This oceanfront home is newly updated and offers direct access to the beach as well as an expansive outdoor entertainment area that is sure to be your favorite spot for summer days! Upon entry, you walk into the home\'s sitting room, which has a dining table
Hot HOT 58
11 Junket Icone Collection Icon
House -
$1,242.00 - $3,146.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 2 half baths
Guests 18 guests
Rating 4.9 (10)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 7 Sea Front is a recently updated, elegant 2nd row ocean home with a golf simulator. Located in Burkes Beach, this home has 7 bedrooms with great porches, a private pool, and a game room featuring a brand new golf simulator and ping pong table. This home is
Hot HOT 91
7 Sea Front Icone Collection Icon
House - Pet Friendly
$753.00 - $1,975.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 24 guests
Rating 5 (11)
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
Hot HOT 55
15 Sea Lane Fairway Collection Icon
House -
$284.00 - $764.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This 4-bedroom, 4.5-bathroom home is in the heart of Sea Pines Plantation. This cozy home features multiple living spaces throughout the home, making it perfect for large groups of friends and families. Relax and unwind by the pool and newly renovated deck or
2 Tupelo Drive Fairway Collection Icon
House -
$328.00 - $946.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 5 (13)

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