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.
60 properties available
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
**FREE POOL & SPA HEAT FOR MARCH-MAY**47 Off Shore Dr is an incredible opportunity for a relaxing getaway! This 3-bedroom, 2.5-bath home is located in Palmetto Dunes and offers a perfect blend of privacy and convenience. Being nestled in a quiet area yet still close to Shelter Cove Towne Center & Harbour for various activities such as dinin
*** New Kitchen Renovation Coming Spring 2026***27 Corine Lane, Hilton Head Island is a luxurious 3-story home nestled in the picturesque Singleton Beach area. This stunning property features a private pool and elevator, adding to the convenience and comfort of your stay. With 7 bedrooms and 7 bathrooms, there's plenty of space for everyone to
10 Sea Front Lane is a new 8 bedroom 9 bathroom property ready for summer 2026! Each room is designed to offer a serene and sophisticated ambiance, perfect for relaxation and rejuvenation. The estate features breathtaking views of both the marsh and the ocean, providing a picturesque backdrop for your stay. The home is equipped with top-of-the
This remarkable oceanfront estate showcases 7 bedrooms and 7.5 bathrooms, exuding unmatched beauty and luxury. 3 Singleton Beach Place is positioned in the perfect location, granting effortless access to nearby local restaurants, and shopping centers. The focal point of this home is its splendid open kitchen, boasting a double oven and an expansive
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
4 Collier Beach Road, Hilton Head Island, is an oceanfront house with 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. The open concept kitchen offers top-of-the-line Wolf and Sub-Zero appliances. Enjoy the private pool and unbeatab
9 Sandy Beach Trail, Hilton Head Island. Welcome to your custom-built vacation home! This stunning property features an open-concept layout with the kitchen, living, and dining areas facing the pool, creating a seamless indoor-outdoor experience for the whole family. The game room in the garage and top-floor living room provide plenty of options fo
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
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
133 Dune Lane, Hilton Head Island is a 4-bedroom, 4-bath oceanfront home epitomizes casual beach living at its finest. Wake up to breathtaking views of the ocean from every room, including the kitchen, living room, dining room, and all four bedrooms. The spacious and comfortable bathrooms ensure a relaxing stay. Recent renovations have revitalized
This gorgeous home is just a short walk to the beach from a quiet seaside community in Burkes Beach. The lower floor houses the garage and a game area that looks out to the beautiful pool, which is great for family fun in the sun. The main floor has an open room concept where the kitchen, living room, and dining area flow into each other. There is
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