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.
61 properties available
9 Singleton Beach, Hilton Head Island. This oceanfront gem is a 10/10 with awe-inspiring views! Ideal for multiple families, this stunning seven-bedroom, seven-and-a-half-bathroom home spans three stories with an elevator. Professionally decorated, it boasts breathtaking panoramic views from most rooms. Four oceanfront bedrooms feature private balc
40 Bradley Beach is an excellent choice for families and groups looking for a well appointment and conveniently located vacation rental on Hilton Head Island. With 4 bedrooms and 3 and a half baths, as well as a private pool, this home offers ample space and amenities for guests to enjoy. The mid-island location is ideal for exploring the area, and
29 Singleton Beach, Hilton Head Island is a modern home ideal for large groups, families with kids, or couples seeking a retreat! Its open-concept floor plan includes a sleek gourmet kitchen flowing into the dining room, perfect for meal preparation and socializing. After a day of adventures, unwind in the master suite with its oversized ensuite ba
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
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
**FREE SPA HEAT ALL YEAR**49 Off Shore Drive, located in the Palmetto Dunes Oceanfront Community, offers a wonderful vacation experience with its spacious and beautifully decorated 4-bedroom, 4-bath layout. The highlight of this property is its private pool and hot tub, providing ample opportunity for relaxation and enjoyment. Additionally, the pri
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
This property is now under new ownership and the owners are keen to make this already beautiful and spacious house lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a magnificent 6-bedroom, 5.5-bathroom, pet friendly home accommodating up to 16 guests making it perfect for family reunions or large ga
20 Horvaths Peninsula, 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 flo
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
Welcome to 2 Abalone Lane, a stunning new 5-bedroom, 5-bathroom home just steps from the beach! This luxurious property features a spacious open-concept living area, a game room with a Ping Pong table, and an elevator for easy access. Enjoy breathtaking ocean views from the balcony and relax in beautifully appointed bedrooms. Ideal for families or
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
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