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 54 properties available
18 Sand Dollar, Hilton Head Island. Your search for the perfect vacation rental ends here! With 7 bedrooms, 7 bathrooms, and an open-concept floor plan, this property is sure to impress. The oversized chef’s kitchen is perfect for cooking up delicious meals for the whole group. Upstairs, enjoy family fun with the pool table, ping pong, and Fo
Hot HOT 95
18 Sand Dollar Road
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 20 guests
Rating 4.7 (79)
13 Moonshell Rd, Hilton Head is a perfect retreat for a coastal escape. With its five bedrooms and three bathrooms, it offers ample space for guests to relax and unwind. The spacious fenced backyard with a private pool and outdoor bar provides a wonderful setting for outdoor gatherings and leisurely days by the pool.Its convenient location, just a
Hot HOT 36
13 Moonshell Road
House
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 12 guests
Rating 4.7 (52)
31 Singleton Beach Place in Hilton Head Island, South Carolina epitomizes luxury living at its finest. With over 5,500 square feet of living space, this 6-bedroom, 9-bathroom residence offers an unparalleled level of comfort and sophistication.Upon entering, guests are greeted by a seamless open floor plan that effortlessly blends the chef's ki
Hot HOT 108
31 Singleton Beach Place
House
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 20 guests
Rating 4.9 (42)
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 50
1 Barrier Beach Cove
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Rating 5 (7)
3 Sutherland, Hilton Head Island. This updated 6-bedroom house, nestled within the prestigious private community of Palmetto Dunes, presents the perfect coastal retreat just moments from the beach! Boasting an open layout, it's ideally suited for accommodating large groups, ensuring everyone can gather comfortably. The spacious bedrooms offer a
Hot HOT 17
3 Sutherland Court
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.7 (23)
35 Crabline Court is a 4-bedroom, 4.5-bath modern coastal home offers a private pool and an oversized front balcony overlooking the prestigious community of The Village at Singleton Beach.  This property is situated next to Chaplin Park which offers tennis, basketball, open fields and a great playground for kids, and best of all, it's a qu
Hot HOT 45
35 Crabline Court
House
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.7 (9)
2 Collier Beach, Hilton Head Island. Experience luxury living at its finest in this magnificent oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool. Each bedroom comes with its own private bath, ensuring maximum comfort and convenience for all guests. The beautiful kitchen is perfect for culinary delights, while numerous balconies o
Hot HOT 51
2 Collier Beach Road
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.6 (36)
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 53
44 Bradley Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 15 guests
Rating 4.6 (29)
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 79
8 Terra Bella Trace
House
Bedrooms 6 bedrooms
Bathrooms 8 baths
Guests 18 guests
Rating 5 (5)
Prepare to have your dreams come true at 7 Singleton Beach Place! This breathtaking oceanfront property has undergone a complete renovation, ensuring that every aspect of your stay is nothing short of extraordinary. With direct, private beach access just steps away from your door, you'll have the pristine sands and sparkling waters of Hilton He
Hot HOT 47
7 Singleton Beach Place
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.8 (8)
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 61
10 Collier Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 4.9 (31)
4 Collier Beach Road, Hilton Head Island, is an oceanfront house boasting 6 bedrooms and 6.5 bathrooms, comfortably accommodating up to 18 guests. Its spacious layout is perfect for large groups, with two living areas for added convenience. Enjoy the private pool and unbeatable oceanfront views from the back deck. With a private boardwalk leading d
Hot HOT 20
4 Collier Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Rating 4.8 (28)

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