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
42 Bradley Beach, a 6 bedroom, 4.5 bath home with private pool, offers not only a great mid island location, but is among our most value attractive properties for families and groups. This property is also located next to Driessen Beach Town Park with playground equipment for the kids, comfort stations, and is just a four-minute walk to the beach o
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 th
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
37 Bradley Beach, Hilton Head Island, is a four bedroom, three bathroom charming home that boasts a partial view of the ocean from its front porch, ensuring a warm reception for all guests. Step inside to the main level, where you'll find a spacious great room featuring stunning travertine tile floors. The fully-equipped kitchen, complete with
12 Whelk Street is an exquisite property situated on Bradley Beach. With its recent renovation and luxurious amenities, it offers a fantastic vacation experience. The five bedrooms and five bathrooms provide ample space for guests, and being just 145 feet from the beach ensures easy access to the beautiful shoreline. The four-story layout, with an
8 Sandy Beach Trail offers in ALL! Steps to beach and park, private pool, two living areas, game room! This will make the perfect vacation rental home to create long lasting memories with family and friends!The main floor of the home features an expansive kitchen with granite countertops, a large island and plenty of space for entertaining and cook
4 Sandy Beach Trail, Hilton Head Island is a Burke's Beach luxurious third-row vacation home offers an unparalleled retreat for guests seeking relaxation and comfort. Boasting six bedrooms and six-and-a-half bathrooms, this pet-friendly abode provides ample space for families and friends to gather and unwind. Step inside to discover a meticulou
41 Bradley Beach is recently renovated with updates that include: New paint throughout, new living furniture, new carpet upstairs, new flooring on first floor, new carpentry work throughout garage stairwell. Do not miss out on this newly renovated property! Looks like a brand new house!!This amazing 6-bedroom, 4.5-bathroom home is ideal for multipl
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
1 Barrier Beach Cove, Hilton Head Island, is your ultimate vacation destination! Completed in 2023, this brand-new 6-bedroom, 6 1/2-bathroom residence offers a luxurious escape just moments from the beach. With a spacious private pool and spa, you can relax and unwind in style. Located adjacent to Chaplin Park, guests can enjoy easy access to ameni
This magnificent 6 bedroom and 5.5 baths with an elevator accessible to all floors! This home sleeps 16 making it the perfect spot for family reunions or large gatherings. Outside is a fantastic deck which overlooks the pool and spa. The yard is fully fenced in, perfect for privacy, the little ones, and the furry ones. Beautiful lawn furniture incl
4 Collier Beach Road, Hilton Head Island, is a newly updated oceanfront house with 6 bedrooms and 6.5 bathrooms, it comfortably accommodates up to 18 people. You'll love the spacious layout, perfect for large groups, and there are two living areas for added convenience. Plus, there's a private pool to enjoy! The best part…the unbeata
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