Vacation Rentals with Private Pools in Hilton Head

Make the most of your Hilton Head getaway with a place to swim and unwind right outside your door. Our Hilton Head vacation rentals with private pools are houses suited to different group sizes and travel plans. Browse the homes below to find a space for your stay, whether you want to spend most of your time by the pool or come back for a swim after a day exploring the island.

Private pool at a rental house, with poolside seating

Enjoy Your Own Poolside Retreat

A private pool gives your group more freedom to enjoy the day at its own pace. Start with a morning swim, take a break from the beach during the afternoon, or settle in for an evening together at the house. You can spend time by the water without planning around a shared pool’s hours or other guests. 


These Hilton Head house rentals with private pools offer a range of layouts and settings. Some are a short walk from the beach, while others are close to golf, shopping, and dining. Use the listings to find a home with enough bedrooms and space for everyone, then choose the location that works for your plans.

More to Enjoy at the House

The pool is the centerpiece, but many homes also have space to cook, dine, and gather between outings. Across the collection, you’ll find houses with kitchens, patios or decks, outdoor seating, and private grills. Some listings include extras such as bikes, beach carts,  and fire pits.

Those spaces make it easy to turn a pool day into a full day together: prepare lunch at the house, eat outside, and head back to the water when you’re ready. If you have a particular setup in mind, check the photos and amenities for each home. Outdoor dining areas, shade, grills, and other features differ from one property to the next.


Fenced in backyard patio with a patio dining set and grill

Before You Book Your Private Pool Home

Pool features and terms vary from house to house. Some pools can be heated for an additional fee, sometimes only during certain months; some homes also have a spa. Check the property description for the details before booking, especially if swimming in cooler weather is important to your plans.

If you need help finding a home with a particular pool feature, contact The Vacation Company team. They can help narrow the options without requiring you to check every listing yourself.



Properties Available 194 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-
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

1 Bittern Street Rating 4.9 (25)
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 7 guests
Discover this charming 3-bedroom beach cottage, ideally located just minutes from Coligny Plaza, Celebration Park, and Hilton Head\'s beautiful sandy beaches — the perfect island escape for a weekend getaway or an extended stay! Enjoy the fresh coastal vibe with all-new bathrooms, stylish updated décor, and a relaxed, welcoming atmosphere. Step ou
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

1 Dove Street Rating 4.9 (31)
Forest Beach Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 7 guests
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
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

12 Deer Run Lane Rating 5 (98)
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
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
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

128 Dune Lane Rating 4.9 (50)
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 6 guests
Looking for a backyard you will never want to leave? Then look no further than 14 Sea Lane. This 3-bedroom renovated home in Palmetto Dunes is near the ocean and provides lots of privacy, perfect for the entire group! When entering this ranch-style home, you will walk up just a few steps to the front door and immediately be greeted by a large famil
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

14 Sea Lane Rating 5 (6)
Palmetto Dunes
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 12 guests
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
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

15 Ibis St Rating 5 (45)
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 6 guests
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
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

15 Pelican Rating 5 (48)
Forest Beach
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
This charming home sits on the 17th Fairway of the Atlantic Dunes Golf course with tons of outdoor space and a private courtyard with an outdoor shower. Light, bright, modern interior with tile floors throughout, new bathrooms, and brand new kitchen cabinets and counters. It\'s truly a unique property that is perfect for summer and fall, welcoming
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

163 North Sea Pines Drive Rating 5 (30)
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
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
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

21 Windjammer Court Rating 5 (52)
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 8 guests
Experience coastal living at its finest in this exquisite home at 22 Windjammer, located in the prestigious Sea Pines community. This beautifully designed property features spacious interiors, elegant furnishings, and an abundance of natural light, creating a warm and inviting atmosphere. The open-concept layout includes a modern kitchen equipped w
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

22 Windjammer Court Rating 5 (4)
Sea Pines
Bedrooms 3 bedrooms
Bathrooms 2 full baths & 1 half bath
Guests 7 guests
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
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

3 Scaup Court Rating 5 (43)
Sea Pines Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
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
sand-dollar Special
Winter on Hilton Head 2027 -Stay Longer and Save

❄️ Trade the winter weather for a little more time on Hilton Head Island!

Book a stay of 22 nights or longer during January or February and enjoy 10% off your stay at participating Vacation Company properties.

Whether you're working remotely, escaping the cold, or simply looking for an extended Lowcountry getaway, winter is one of the best times to slow down and enjoy Hilton Head.

4 Iron Clad Rating 5 (43)
Palmetto Dunes
Bedrooms 3 bedrooms
Bathrooms 3 full baths & 1 half bath
Guests 10 guests

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