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. 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 59
11 Junket Icone Collection Icon
House -
$1,053.00 - $4,106.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 2 half baths
Guests 18 guests
Rating 4.8 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. A stunning 5-bedroom home in Palmetto Dunes offering breathtaking golf views and a charming peek-a-boo ocean view! Access to this home is through the garage or the side door from the driveway, leading you into the laundry room and then seamlessly into the kit
32 Full Sweep Fairway Collection Icon
House
$337.00 - $1,167.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 12 guests
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. The grand entrance staircase will transport you to another world through the Italian-style portico, where you are immediately greeted by an expansive ocean view. Walking into the main house, you are greeted by a beautiful, curved staircase leading you up to
Oceanfront Oceanfront
Oceanfront
7 Junket Icone Collection Icon
House - Pet Friendly
$1,273.00 - $3,546.00 / per night
Bedrooms 6 bedrooms
Bathrooms 7 baths
Half Bathrooms 2 half baths
Guests 15 guests
Rating 4.8 (8)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This fantastic 2nd row of the ocean is nestled in the palms of the Palmetto Dunes resort. With 6 bedrooms and 6.5 baths, this low-country home is the perfect getaway for family and friends! A circular drive leads to a beautiful entrance way and wraparound p
3 Iron Clad
House -
$691.00 - $2,141.00 / per night
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 12 guests
Rating 4.7 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 10 Cassina Lane is a completely renovated, beautiful Cape Cod-style oceanfront home located right in South Forest Beach, just minutes away from the very popular Coligny Plaza. Featuring 5 bedrooms and 4.5 bathrooms, it is perfect for your next family getaway.
Oceanfront Oceanfront
Oceanfront
10 Cassina Lane
House
$499.00 - $855.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 12 guests
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This spacious home embodies beach cottage vibes with its open layout and tastefully decorated interior! Soaring ceilings and lots of windows provide the great room with plenty of natural sunlight. In the living room, you will find plenty of plush seating arou
Hot HOT 56
31 Sand Dollar Road
House - Pet Friendly
$197.00 - $775.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 4.8 (8)
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
Hot HOT 54
19 Sand Dollar
House -
$550.00 - $1,262.00 / 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. This oceanfront home sits in the prestigious Palmetto Dunes Resort and offers panoramic ocean views from every angle. The great room, kitchen, and dining area make up the great room of the home; the extremely open floor plan allows for an easy flow and plent
Hot HOT 68
10 Ketch Icone Collection Icon
House -
$987.00 - $3,222.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 5 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Looking for the perfect vacation retreat? You’ve come to the right spot! This home is completely renovated! The inside of the home has new floors, new light fixtures, a new stairway, a newly updated kitchen with stainless appliances, a new laundry room, and
Hot HOT 63
57 North Sea Pines Icone Collection Icon
House -
$370.00 - $1,432.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 5 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This completely remodeled Sea Pines home sits on the 11th fairway and 15th green of the Harbour Town Golf Course! With 5 bedrooms and 6 bathrooms, this sunlight-filled home can host up to 14 guests comfortably. As you enter the home, you are met with an extr
100 Baynard Cove Fairway Collection Icon
House -
$511.00 - $1,460.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 14 guests
Rating 5 (7)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Can you just imagine hearing the birds chirping and the wildlife rustling in the greenery as you watch the herons wading in the lagoon? Can you hear the ping of the golfer’s tee shot? Is the contact between the driver and the golf ball making the sweetest sou
42 Stoney Creek Fairway Collection Icon
House -
$557.00 - $2,624.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 15 guests
Rating 4.8 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. The beach is calling at 62 Mooring Buoy! This sun-filled home is located in beautiful Palmetto Dunes, just a one-minute walk to the beach for toes in the sand. No crossing of streets, located on the beach path! Featuring 4 bedrooms and 4 baths, there is ple
Recently Updated Recently Updated
Recently Updated
62 Mooring Buoy
House -
$389.00 - $1,319.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.9 (34)

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