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 65 properties available
Welcome to 36 Red Oak! This pet-friendly Sea Pines home has an extremely open floor plan with soaring ceilings to create a charming environment perfect for your next vacation. Three bedrooms and three bathrooms offer enough space to host up to 10 guests comfortably. Multiple living and sitting spaces with brand new flatscreen TVs offer plenty of sp
36 Red Oak Fairway Collection Icon
House - Pet Friendly
$249.00 - $1,219.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 12 guests
Rating 5 (9)
Welcome to the 11 Red Oak! This Sea Pines home is nestled on a quiet street and places you only minutes away from Harbour Town and the sandy beaches! Upon entry, you walk into the sitting room, which has plenty of comfortable seating around the cozy brick fireplace (not for guest use). Soaring ceilings and many large windows produce a light and ai
11 Red Oak
House -
$349.00 - $679.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 4.8 (15)
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 - $626.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 5 (11)
Welcome to 10 Ketch! 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 plenty of space for all. The huge living room boasts stunning views of the
Oceanfront Oceanfront
Oceanfront
10 Ketch Icone Collection Icon
House -
$811.00 - $2,784.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 5 (6)
With a scenic spot on the 11th hole, a private pool and spa to spend the day in, and spectacular views of the lagoon and golf course, this South Carolina home is the perfect vacation spot. Vaulted ceilings make this property feel comfortably spacious, which becomes even more immense when you open the sliding doors to the large deck with views of
38 Stoney Creek Road | Carolina Getaway Fairway Collection Icon
House -
$215.00 - $1,249.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
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 4 bedrooms and 3 bathrooms, it is perfect for your next family getaway. Also featuring a private pool, a screened-in porch, and an outside deck, this home is sure t
Oceanfront Oceanfront
Oceanfront
10 Cassina Lane
House
$537.00 - $1,426.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 12 guests
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)
Welcome to 30 Ruddy Turnstone! With beautiful craftsmanship throughout the well-appointed house. The ground level has a newly refinished pine floor and an open-plan design, with the large kitchen overlooking the cozy living room. There are lots of books to read; there is lots of seating on the sofas; a kitchen bar that seats 4 overlooks the kitchen
30 Ruddy Turnstone | Ruddy Retreat
House - Pet Friendly
$495.00 - $1,281.00 / per night
Bedrooms 5 bedrooms
Bathrooms 6 baths
Guests 14 guests
Rating 4.8 (9)
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 everything you need. Attached to the great room, the Carolina room with a ping pong table i
26 Forest Drive
House -
$235.00 - $526.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 6 guests
Rating 5 (8)
This amazing island getaway is nestled among the pines beside a lagoon on 1.9 acres in the heart of Sea Pines. This beach home offers beautiful high-end finishes in the huge eat-in kitchen and throughout, including the spacious dining room, living room, and first-floor master suite. The media room, bedrooms, and bathrooms are luxurious and comfort
Hot HOT 54
5 Calibogue Cay
House - Pet Friendly
$245.00 - $682.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 5 (2)
Welcome to 5 Jessamine Place, only a 10-minute walk to the best beach on Hilton Head Island! This ranch-style cottage home is newly renovated and beautifully furnished. It offers four bedrooms and four bathrooms to comfortably host up to 13 guests. Nestled on a quiet street with a big yard and private heated pool plus spa, this home is perfect fo
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New Pictures
5 Jessamine Place
House -
$319.00 - $944.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 5 (14)
Welcome to 26 Bradley Circle! Views, views, and more views! What better way to start your day than listening to the surf, enjoying the beautiful marsh with active wildlife, and the ocean just beyond while sipping your coffee on the deck? Gorgeous beach just a 1-minute walk away with secluded access! 26 Bradley is the perfect location on Hilton He
26 Bradley Circle
House - Pet Friendly
$351.00 - $1,156.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 (5)

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