Hilton Head Rentals with Private Pool

Relaxing by the pool is a special part of visiting Hilton Head Island. Enjoy everything Hilton Head has to offer with our Hilton Head rentals with a private pool. Afternoons are hot, and when the sun is high in the sky, jumping into a refreshing pool feels like entering paradise. During your Hilton Head vacation, there’s no better place to hang out than your own private pool. Below you’ll find Hilton Head rentals with private pools. Our vacation rentals with private, heated pools place you in Hilton Head’s best communities. Hilton Head vacation homes with pools are perfect for families and groups. Plunge into an amazing vacation on Hilton Head Island with Vacation Homes of Hilton Head.


Properties Available 56 properties available
This house features 5 bedrooms and 6 bathrooms with space enough for 16.Please review our property photos and our available amenities to make sure this rental is a perfect fit for your needs. We strive to keep this information as up-to-date as possible so you can feel confident in knowing what you are renting.We will send you all necessary pre-arri
Hot HOT 69
7 Abalone Lane
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 16 guests
Rating 5 (1)
14 Collier Beach, Hilton Head Island is a stunning oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grill. The home features a luxurious master suite with breathtaking views of the Atlantic Ocean, a marble bathroom, and a free-form tub. With a privat
Hot HOT 67
14 Collier Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.8 (42)
13 Moonshell, Hilton Head Island is a charming Hilton Head retreat that offers an ideal setting for your coastal escape. Featuring 4 bedrooms and 3 bathrooms, along with a spacious fenced backyard complete with a private pool and outdoor bar, this property is designed for relaxation and enjoyment. Conveniently located just a short 3-5 minute drive
Hot HOT 31
13 Moonshell Road
House
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 12 guests
Rating 4.7 (50)
This home recently underwent a comprehensive transformation, showcasing a fully renovated kitchen, fresh paint, new flooring, updated furniture, and enhanced décor. Situated just 50 feet from the beach path, this home offers stunning views of both the ocean and marshlands. Boasting 7 bedrooms, 5 1/2 bathrooms, a heated private pool, two ocea
Hot HOT 132
3 Collier Court
House Pet Friendly
Bedrooms 7 bedrooms
Bathrooms 5 baths
Guests 22 guests
Rating 4.7 (7)
19 Sand Dollar, Hilton Head Island. Welcome to this charming second-row ocean home blending traditional coastal Carolina styling with high-end details for a memorable beach vacation! Located directly across from a semi private beach, enjoy plenty of space to relax in the surf, sand, and sun. Designed to make the most of its fabulous location, this
Hot HOT 29
19 Sand Dollar Road
House
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 16 guests
Rating 4.8 (16)
20 Horvath, Hilton Head Island is a renovated oceanfront retreat, nestled in the desirable Burkes Beach Area, offers breathtaking views from every floor. With 6 bedrooms and 5 bathrooms, including five king bedrooms and a custom-built bunk area for the kids, it's perfect for families. The open-concept kitchen adds to the seamless flow of the ho
Hot HOT 75
20 Horvath's Peninsula
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.8 (6)
6 Terra Bella Trace, Hilton Head Island is nestled between the salt marsh and the Atlantic Ocean, 6 Terra Bella Trace is a beach lover's paradise. This outstanding property features 6 bedrooms and 8 bathrooms. The chef's kitchen boasts top-of-the-line Wolf and Sub-Zero appliances and an oversized island with wrap-around seating. The open-co
Hot HOT 47
6 Terra Bella Trace
House
Bedrooms 6 bedrooms
Bathrooms 8 baths
Guests 20 guests
Rating 4.8 (38)
133 Dune Lane, Hilton Head Island is a 4-bedroom, 4-bath oceanfront home epitomizes casual beach living at its finest. Wake up to breathtaking views of the ocean from every room, including the kitchen, living room, dining room, and all four bedrooms. The spacious and comfortable bathrooms ensure a relaxing stay. Recent renovations have revitalized
Hot HOT 79
133 Dune Lane
House
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.9 (11)
***EV Car charging outlet (receptacle) in Garage (guest to bring their own charging station)***This beautifully decorated 6 bedroom, 6 bath open concept home has three master bedroom suites with king beds and flat screen TVs. The master bathrooms are simply exquisite, with spa tubs, dual sinks, and separate frameless showers with lavish stone floor
Hot HOT 133
32 Corine Lane
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 15 guests
Rating 4.7 (24)
8 Sandy Beach Trail offers in ALL! Steps to beach and park, private pool, two living areas, game room! This will make the perfect vacation rental home to create long lasting memories with family and friends!The main floor of the home features an expansive kitchen with granite countertops, a large island and plenty of space for entertaining and cook
Hot HOT 27
8 Sandy Beach Trail
House
Bedrooms 7 bedrooms
Bathrooms 6 baths
Guests 19 guests
31 Singleton Beach Place, Hilton Head Island, South Carolina you will experience the epitome of luxury living in this exquisite residence! Boasting over 5,500 sq. ft., this 6-bedroom, 9-bathroom home showcases a seamless open floor plan, complete with a chef's kitchen adorned with premium appliances and tasteful decor, ideal for accommodating l
Hot HOT 59
31 Singleton Beach Place
House
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 20 guests
Rating 4.8 (39)
This stunning, completely renovated oceanfront property will make all of your dreams come true! 7 Singleton Beach Place has direct, private beach access, a private pool, and furnishings that will make you feel right at home!Free Activities Included! Play a round of golf, explore Hilton Head on bicycle or even bring out your inner kid with a round o
Hot HOT 48
7 Singleton Beach Place
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 5 (5)

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