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
"Fairway Palms" is a low-country gem. It is in a lovely private setting in Sea Pines, in the coveted Harbour Town neighborhood. The home is uniquely situated on the 8th fairway of Harbour Town Golf Links, surrounded by two beautiful lagoons. Expansive views wrap around the property of this gorgeous, totally remodeled 3 bedroom, 3.5 bath home. Walk
Hot HOT 53
21 Heritage | Fairway Palms Fairway Collection Icon
House -
$383.00 - $2,149.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 5 (6)
Located in Palmetto Dunes and only a few minutes walk to the beach, this four bedroom home has all you need for the perfect stay on the island. 3 Cartgate offers four bedrooms and four and a half bathrooms, large spacious rooms, an open kitchen and private pool! As you walk into the home, the first floor features a spacious living room that connec
3 Cartgate
House -
$319.00 - $795.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (2)
9 Armada is a gorgeous second row home directly on the beach path in Palmetto Dunes Resort. This spacious 6,800 square foot home is perfect for entertaining, dining, reading, or relaxing! The kitchen features granite counters, two sinks, two dishwashers, a warming drawer, a wine cooler, and bar seating. The kitchen opens to the dining area and gre
Hot HOT 51
9 Armada Icone Collection Icon
House -
$540.00 - $2,140.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 1 half bath
Guests 19 guests
Rating 5 (2)
Fabulous two-story second row home The balconies and decks overlook the incredible pool. Take the secret path through the canopy and reach the beach in a 1-minute walk. This 6-bedroom, 5.5-bath home with 2 living rooms sleeps 15 and promises unforgettable family vacations in a spacious and elegant setting. The first floor has a wide open floor pla
Hot HOT 67
1 Man O War Icone Collection Icon
House -
$788.00 - $2,336.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 15 guests
Rating 5 (7)
Welcome to 9 Flamingo Street in the charming town of Hilton Head! This stunning rental home offers a picturesque and convenient location, perfect for creating unforgettable vacation memories. This two-story retreat is designed for groups, with a private pool, a huge outdoor dining table, and five bedrooms with multiple bunk options. Spread out betw
9 Flamingo Street
House -
$263.00 - $1,111.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 15 guests
Rating 4.6 (3)
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 ceilings and access to a deck overlooking the backyard and pool. A dining table with six chai
35 Battery Road
House -
$211.00 - $649.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)
32 Bradley Beach Road is a gorgeous beach house located a short walk to the beach, sleeping 9 guests in 3 bedrooms, 3 bathrooms, and a bonus room. This lovely home is exceptionally well maintained and has ample room to spread out in the living room, which has a sofa that converts into a queen bed. The kitchen is equipped with stainless steel applia
Hot HOT 50
32 Bradley Beach Road
House - Pet Friendly
$193.00 - $475.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 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 92
9 Guscio Way Icone Collection Icon
House -
$1,137.00 - $3,373.00 / per night
Bedrooms 8 bedrooms
Bathrooms 8 baths
Guests 20 guests
Rating 5 (11)
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 sound? Can you imagine relaxing by the inviting pool while hearing the sizzle of your steak co
Hot HOT 78
42 Stoney Creek Fairway Collection Icon
House -
$599.00 - $2,599.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 15 guests
Rating 4.7 (4)
Welcome to Fairway Breeze! A beautifully renovated four-bedroom, three-bath golf course home in the gated oceanfront resort of Palmetto Dunes. Upon entry, be invited into the living room with a view of the pristine fairway of the George Fazio Golf Course. Separating the living room and dining room is a double-sided fireplace. Get a little work do
7 Ginger Beer | Fairway Breeze Fairway Collection Icon
House - Pet Friendly
$267.00 - $649.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 4.9 (13)
Stunning 4-bedroom, 3-bathroom home with lagoon views on Mooring Buoy Less than a 5-minute walk to the ocean or access via the seasonal Dunes Buggy Beach Shuttle! This gorgeous Palmetto Dunes home has been completely renovated to offer guests a luxurious vacation experience while making you feel right at home. Floor-to-ceiling windows allow for li
183 Mooring Buoy
House -
$341.00 - $471.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 5 (4)
This oceanfront stunner was built in 2019 and offers amazing views as well as direct access to the beach with a private boardwalk. Walk into an amazing great room to unwind from a day out in the sun. The living room has two couches and two comfy chairs that lead out to the first balcony to soak in the picture-perfect view of the ocean. The kitche
Hot HOT 96
103 Dune Lane Icone Collection Icon
House - Pet Friendly
$1,376.00 - $3,933.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 20 guests
Rating 5 (8)

Tell us what you're looking for and someone will contact you with available options.

I agree