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.
56 properties available
41 Bradley Beach is a great option for a beach vacation on Hilton Head Island. This 6-bedroom, 4.5-bathroom home is ideal for larger groups or families and has been recently renovated with new paint, living furniture, flooring and a new front porch. The home is just a short walk from the beach and includes a private backyard pool and offers plenty
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
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
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
3 Shore Crest Lane, Hilton Head Island. Luxury awaits in this custom-built 5-bedroom home in Burkes Beach, just a 5-minute walk to the beach and adjacent to Chaplin Park. Enjoy high-end finishes, a chef's kitchen, sunroom, covered deck, pool table, private pool, and an outdoor kitchen. This property is designed for the ultimate vacation experie
4 Brigantine, Hilton Head Island is your perfect family vacation at this second-row home! With 6 bedrooms, each with a full bath, and ocean views from the second-floor living area, this home offers comfort and relaxation. Enjoy convenience with an elevator, oversized pool, and beach access just across the street. The large pool area boasts a table
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
44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 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
4 Catboat, Hilton Head Island is an open-concept floor plan with spacious bedrooms, each boasting its own bathroom, and an oversized private pool. Located just steps from the beach and close to all the amenities of Palmetto Dunes Oceanfront Resort, including tennis, golf, restaurants, and the renowned General Store, this vacation rental offers conv
1 Shore Crest Lane, Hilton Head Island is a beautiful home built in 2022 and offers 5 bedrooms & 5 bathrooms, a large pool and a relaxing outdoor entertainment space. This lovely beach house is just a quick 3-5 minute walk to the Burkes Beach, is right next to Chaplin Park (tennis, basketball, playground, and beautiful athletic fields). Do not
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 k
5 Shore Crest Lane is a newly constructed home that offers 6 bedrooms all with private bathrooms, a luxurious chef's kitchen, private heatable pool and heatable spa, and multiple entertaining areas. This property was built with renters in mind to ensure amazing memories are created and includes up to $1000 in FREE activities. 5 Shore Crest Lane
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