Homes with a Private Pool

Stay in style with a private pool on Hilton Head Island. While vacationing on Hilton Head, there’s nothing more relaxing than enjoying the pool with your friends and family. Our Hilton Head vacation rentals with private pools give you a place to dive into a refreshing afternoon. Located in Hilton Head’s best neighborhoods, with great access to beaches, golf courses, and family entertainment, these special vacation homes are perfect for families and groups. Book your Hilton Head poolside vacation today!


Properties Available 181 properties available
Walk to the Atlantic Ocean and Coligny Plaza for dining and shopping... what more do you need!?? Three (3) bedrooms and two (2) full bathrooms offer sleeping arrangements for up to seven. Updated furnishings complete the look of this home, providing a "shore to please" vacation. Complete with a backyard oasis, including a private pool and screened-
1 Bittern Street
House
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 7 guests
Rating 4.6 (3)
West Garrison is located in a quiet neighborhood within Sea Pines Resort. The main level of the house has a large living and dining area to accommodate all family gatherings. A second living area on the main level is perfect for watching TV. Both living areas have a queen sleeper sofa. The main level showcases a master bedroom with an en-suite bath
1 West Garrison
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 10 guests
Rating 5 (4)
Your very own private retreat in the heart of Sea Pines! This 3-bed, 3-bath single-level home offers an open concept with multiple living spaces for the entire family. The Tommy Bahama décor throughout and Brazilian cherry wood floors are highlighted by the numerous skylights which allow an abundance of natural light in. Upon entering, you will fin
12 Deer Run Lane
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (2)
128 Dune is just steps away from the glimmering Atlantic Ocean! This 3 bedroom, 3.5 bath home with a private *heated pool has a prime location in North Forest Beach. Beautiful hardwood flooring in the living room, quartz countertops in the kitchen, and coastal chic furniture are just a few of the upgrades. The bathrooms have been completely redesig
128 Dune Lane
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 6 guests
Rating 5 (4)
This bright and spacious home with beautiful beach decor is only steps away from the ocean. The first floor offers an open living room and kitchen with large windows and high ceilings. A separate dining room, bar seating, and a card/breakfast table exist. A king bedroom and 2 full baths are also on this floor. The upper floor hosts two guest bedroo
15 Ibis St
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Rating 5 (5)
Welcome to this beautiful ranch-style beach house, perfect for your next getaway! Complete with a backyard oasis, including a private pool and screened-in porch... it\'s ideal for your island escape. There are three (3) bedrooms and two (2) full bathrooms, offering sleeping arrangements for eight. The furnishings complete the look of this home, pro
15 Pelican
House
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (7)
Overlooking the 10th tee of Harbour Town Golf Links, this beautifully decorated home features three bedrooms and 3.5 bathrooms. Take a short stroll to the Sea Pines Racquet Club, the Harbour Town Clubhouse, and the Harbour Town Yacht Basin. Stay in and enjoy the poolside views of the golf course from the living room, private den, and two of the mas
21 Windjammer Court
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 8 guests
Rating 5 (3)
This 3-bed, 3-bath traditional Sea Pines beach home with a private pool is just 3rd row from the ocean! This ranch-style home has a large open kitchen and Corian countertops. The kitchen area encompasses a nice dining area and a glassed-in Carolina room. Nearby to the Carolina room is a spacious living room that looks over the pool. Sliding doo
22 Surf Scoter
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Rating 4.5 (2)
This charming 3-bed, 3-bath dog-friendly vacation home is in the South Beach area of Sea Pines. *Heated private pool, spa, and just a short walk to the beach; this house is perfect for families or small groups. Also close by are all the activities offered by the South Beach Marina, including charter fishing, water sports, shopping, entertainment, a
3 Scaup Court
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (6)
This 2nd row, a low country-style beach house in Palmetto Dunes Plantation, is built to make vacation dreams come true. This home had a full kitchen renovation completed in January 2023. Wide wrap-around porches and an updated Carolina room provide a comfortable place to enjoy ocean breezes morning, noon, and night! Whether on the deck peering out
4 Iron Clad
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 10 guests
Rating 5 (7)
This tastefully renovated 3-bedroom, 3-bath dog-friendly home has a private heated pool and is a 5-minute walk to the beach! Located in the beautiful Sea Pines Plantation, a quick stroll to the South Beach Marina Village offers shopping, restaurants, and nightly entertainment. This charming one-level home boasts an open floor plan with a kitchen
4 Merganser Court
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 4.9 (18)
Charming and spacious, this secluded 3-bed, 3-bath home overlooks a lush lagoon. The private *heated pool, surrounded by a large deck, offers a free standing hot tub, screened porch, plenty of lounge chairs, firepit and a gas grill. The perfect space for outdoor relaxing. Cherry-wood flooring greets you and extends to the dining room, with seatin
48 Kingston Rd
House
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
Rating 5 (8)

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