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.
53 properties available
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 and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own private bath, ensuring maximum comfort and convenience for all guests. The beautiful kitchen is
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
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
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
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
Discover coastal luxury at 25 Bradley Circle, a brand-new vacation rental home ready for summer 2025! This stunning property features 6 spacious bedrooms and 7.5 bathrooms, offering ample room for large families or groups. With two elegant living areas, a rooftop deck perfect for sunset views, and a ground-floor pool complemented by a heated spa, t
Welcome to the future of luxury vacationing on Hilton Head Island! This stunning pre-construction home on Shell Midden Lane offers the perfect vacation retreat for discerning guests. Boasting 6 spacious bedrooms, 6.5 bathrooms, a private pool, elevator, and multiple balconies, this low-country oasis provides both comfort and elegance. With 3,701 sq
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
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
Discover the perfect getaway in this stunning 6-bedroom, 5-bathroom custom home, built in 2024! Located just moments from Folly Field Beach, this is an ideal vacation retreat. Enjoy ultimate relaxation with a private pool, an elevator for easy access, and designer touches throughout, including elegant wainscoting, stylish area rugs, and plush beddi
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
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