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
4 Collier Court, Hilton Head Island is a property that is boasting fresh paint and décor enhancements updates, this home is a true gem. Just 50 feet from the beach path, it offers breathtaking views of the ocean and marsh. With 6 bedrooms, 6.5 bathrooms, a heated private pool, and 3 ocean-view porches, each bedroom with its private bat
27 Singleton Beach, Hilton Head Island is a direct oceanfront home that accommodates up to 18 guests and boasts an open-concept floor plan with breathtaking 360-degree views of the ocean and marsh. Enjoy a chef’s kitchen, 4 luxurious master suites with deep soaking tubs and oversized walk-in showers, dedicated work desks, and additional
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
19 Singleton Beach Place, Hilton Head Island, is a 6 bedroom, 6.5 bathroom oceanfront home with a private pool and boardwalk, elevator, and chef's kitchen. This property offers a luxurious retreat for vacationers and includes up to $1000 in FREE activities with every reservation. The breathtaking ocean views, upscale finishes, and elegant d&eac
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
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,
16 Singleton Shores Manor, Hilton Head Island.Enjoy marsh and ocean views from every level of this home. Step into the open and bright living area, complete with a wet bar, pool table, and access to your private pool deck. Upstairs, an updated kitchen, second living area, and spacious dining room await, perfect for family gatherings. Retreat to the
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
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
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
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
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