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
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
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
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
3 Collier Court, the kitchen features state-of-the-art appliances and modern finishes, perfect for preparing gourmet meals. The spacious living areas, adorned with stylish and comfortable furniture, invite relaxation and socializing. Each of the 7 bedrooms is uniquely decorated, offering cozy retreats for guests, while the 5 1/2 bathrooms provide a
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
FREE activities included with our signature Southern Hospitality Pass! Your pass includes one free round of golf daily at partner courses like the Heritage Collection and the Brown Group. Note: This is per day, not per person. You also receive one free round of miniature golf each day at Adventure Cove and one complimentary bike from Island Cruiser
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
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
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
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
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
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