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.
58 properties available
*READY FOR MAY 2026 - CURRENTLY BEING FURNISHED AND NEW PHOTOS TO COME - CALL 843-715-2208 FOR QUESTIONS* PRICED TO REFLECT CURRENT CONDITION - SEE LAYOUT DESCRIPTION BELOW FOR BED AND ENSUITE INFORMATION*Discover a breathtaking new home on Shell Midden Lane, designed for the most discerning travelers. This exquisite property features 7 spacious be
37 Bradley Circle, Hilton Head Island, is a four bedroom, three bathroom home nestled in a quiet beach area of Burkes Beach. Step inside to the main level, where you'll find a cozy living room, large TV and access to the upper dining deck. The fully-equipped kitchen, complete with stainless steel appliances and granite counter
*** New Kitchen Renovation Coming Spring 2026***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
35 Crabline Court is a 4-bedroom, 4.5-bath modern coastal home that 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. Best of all, it's a q
12 Collier Beach Rd in Hilton Head is indeed a wonderful oceanfront home, perfect for a vacation getaway. With its convenient location near Shelter Cove Towne Centre, vacationers can easily explore local shops, restaurants, and attractions. The six spacious bedrooms, private beach access, and stunning ocean views from all levels of the home offer a
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
*READY FOR MAY 2026 - CURRENTLY BEING FURNISHED AND NEW PHOTOS TO COME - CALL 843-715-2208 FOR QUESTIONS* PRICED TO REFLECT CURRENT PHOTOS WITH NO FURNITURE- SEE LAYOUT DESCRIPTION BELOW FOR BED AND ENSUITE INFORMATION*Unveil a stunning new home tailored for the most sophisticated guests. This exceptional property features 7 generously sized bedroo
Luxury Coastal Retreat – Steps from the Beach with Stunning Ocean Views Welcome to 12 Whelk Street, Hilton Head Island’s premier vacation destination, where beachside luxury meets unmatched convenience. Just 145 feet from the pristine sands of Bradley Beach, this recently renovated four-story property offers stunning ocean vi
9 Sandy Beach Trail, Hilton Head Island. Welcome to your custom-built vacation home! This stunning property features an open-concept layout with the kitchen, living, and dining areas facing the pool, creating a seamless indoor-outdoor experience for the whole family. The game room in the garage and top-floor living room provide plenty of options fo
Spring 2026 updates are currently underway including new dining room furniture, new kitchen table & chairs, new lights and new fans throughout. By April 2026, we will have new photos online but please call us with any questions. This property is now under new ownership and the owners are keen to make this already beautiful and spacious house li
This beautiful oceanfront 6-bedroom/ 6.75-bathroom home is everything you have been looking for! With 2 living areas there is plenty of room for your group to have fun, spread out, and relax. Play pool in the top floor media room or practice your swing on the ground floor putting green. Vacationers will enjoy their own private pool (with access to
21 Singleton Beach Place is a luxurious 7-bedroom, 7.5-bathroom oceanfront home is truly a paradise for families or groups seeking an unforgettable retreat. Boasting stunning views of the ocean, its open concept floor plan seamlessly blends indoor and outdoor living, creating an inviting atmosphere for relaxation and entertainment. Each room i
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