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
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)
8 Terra Bella Trace, Hilton Head Island. Indulge in the ultimate oceanfront experience at 8 Terra Bella Trace. This luxurious six-bedroom, eight-bathroom home, completed in late summer 2022, spares no expense. The chef's kitchen boasts top-of-the-line appliances and a spacious island with seating for all. The open-concept kitchen, living, and d
Hot HOT 55
8 Terra Bella Trace
House
Bedrooms 6 bedrooms
Bathrooms 8 baths
Guests 18 guests
Rating 5 (5)
10 Collier Beach, Hilton Head Island is an escape to paradise in this stunning 6-bedroom, 7-bathroom oceanfront home, offering breathtaking ocean views and the ultimate in privacy. Relax by the private pool, enjoy direct access to the beach, and indulge in the luxury of a chef's kitchen. Entertain friends and family in the game room, or let tee
Hot HOT 47
10 Collier Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 5 (24)
44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 13 and has a large 16' x 32' pool, and features an outdoor fire pit perfect for a night hosting around the pool or a cool day in the fall! There is plenty of seating and the home is conveniently located at the very end of Bradley Road with a fenced in patio givin
Hot HOT 52
44 Bradley Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 15 guests
Rating 4.6 (26)
A cozy newly renovated house that offers private comfort and modern conveniences. Located in the sought-after Folly Field area, this home has 4 bedrooms and 3 full bathrooms. You are steps away from the open ocean.A 4-minute walk takes you directly to Folly Field Beach. Don't miss the spectacular sunrises and the feel of the sand between your t
Hot HOT 23
46 Folly Field Road
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 11 guests
Rating 5 (10)
1 Barrier Beach Cove, Hilton Head Island, is your ultimate vacation destination! Completed in 2023, this brand-new 6-bedroom, 6 1/2-bathroom residence offers a luxurious escape just moments from the beach. With a spacious private pool and spa, you can relax and unwind in style. Located adjacent to Chaplin Park, guests can enjoy easy access to ameni
Hot HOT 52
1 Barrier Beach Cove
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Rating 5 (4)
27 Corine Lane, Hilton Head Island is a luxurious 3-story home nestled in the picturesque Singleton Beach area. This stunning property features a private pool and elevator, adding to the convenience and comfort of your stay. With 7 bedrooms and 7 bathrooms, there's plenty of space for everyone to relax and unwind. The home's prime location
Hot HOT 53
27 Corine Lane
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 4.4 (21)
This remarkable oceanfront estate showcases 7 bedrooms and 7.5 bathrooms, exuding unmatched beauty and luxury. 3 Singleton Beach Place is positioned in the perfect location, granting effortless access to nearby local restaurants, and shopping centers. The focal point of this home is its splendid open kitchen, boasting a double oven and an expansive
Hot HOT 68
3 Singleton Beach Place
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 26 guests
Rating 5 (5)
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 153
3 Collier Court
House Pet Friendly
Bedrooms 7 bedrooms
Bathrooms 5 baths
Guests 22 guests
Rating 4.7 (7)
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 43
7 Singleton Beach Place
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 5 (5)
19 Singleton Beach Place, Hilton Head Island, is a 6 bedroom, 6.5 bathroom oceanfront home with a private pool and boardwalk, elevator, and chef's kitchen. This property offers a luxurious retreat for vacationers and includes up to $1000 in FREE activities with every reservation. The breathtaking ocean views, upscale finishes, and elegant d&eac
Hot HOT 45
19 Singleton Beach Place
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.8 (34)
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)

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