Hilton Head House Rentals With 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!
You can filter by bedrooms, guests, pet friendly and much more! Looking for oceanfront rentals? Use the oceanfront filter to select all Hilton Head oceanfront rentals with pool.
Booking your dream vacation is easy. Simply browse our selection of Hilton Head oceanfront rentals, choose your dates, and secure your reservation online. Our friendly team is also available to help you find the perfect property to suit your needs.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!
You can filter by bedrooms, guests, pet friendly and much more! Looking for oceanfront rentals? Use the oceanfront filter to select all Hilton Head oceanfront rentals with pool.
Booking your dream vacation is easy. Simply browse our selection of Hilton Head oceanfront rentals, choose your dates, and secure your reservation online. Our friendly team is also available to help you find the perfect property to suit your needs.
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-
![]()
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.
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
![]()
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.
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
![]()
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 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
![]()
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.
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
![]()
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.
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
![]()
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.
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
![]()
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.
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
![]()
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.
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
![]()
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.
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
![]()
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.
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
![]()
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.
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
![]()
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.
More Results Based On Your Search
Tell us what you're looking for and someone will contact you with available options.