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.
61 properties available
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
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
Escape to Island Bliss at “Slightly Shady” – Your Forest Beach RetreatJust a 3-minute stroll to the sand and half mile from Sea Pines access, Slightly Shady is a six-bedroom coastal escape perfectly situated at 4 Elderberry Lane in the heart of Hilton Head’s sought-after Forest Beach area. With the beach at one end of the st
35 Crabline Court is a 4-bedroom, 4.5-bath modern coastal home that offers a private pool and an oversized front balcony overlooking the prestigious community of The Village at Singleton Beach. This property is situated next to Chaplin Park which offers tennis, basketball, open fields and a great playground for kids. Best of all, it's a q
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
This exceptional property features 7 generously sized bedrooms and 7.5 bathrooms, complemented by a private pool and an elevator for added ease and accessibility. With 4,639 square feet of heated living space, this coastal oasis perfectly blends comfort with elegance. The generous outdoor spaces create an ideal retreat for families or large groups
21 Horvath, Hilton Head Island. This stunning oceanfront home offers 5000 square feet of luxury living space, featuring 6 bedrooms and 6 bathrooms. The open-concept living area and chef’s kitchen provide the perfect space for gatherings, while the oversized oceanfront pool deck and propane grill are ideal for outdoor entertaining. Enjoy direc
Welcome to 15 Collier Beach Road. This three-level home offers ocean, marsh, and tidal creek views. The main level features a gourmet kitchen with a large island, a family room with an 82-inch smart TV, and a dining room, all with water views. The second level has three en suite bedrooms, including a master suite with a king bed, sitting area, pull
Welcome to the future of luxury vacationing on Hilton Head Island! This stunning newly built 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 square
35 Full Sweep, Hilton Head Island is a recently renovated 5-bedroom/5-bathroom home, located inside Palmetto Dunes Plantation, features a large private pool and new furniture throughout. With 3 King Primary bedrooms, each with private en-suite bathrooms, and a fourth bedroom with a pullout sofa and work space, it accommodates various needs. The lar
Welcome to 3 Sutherland, a six-bedroom retreat located in the heart of Palmetto Dunes — one of Hilton Head Island’s most sought-after private communities. Just moments from the beach, this home offers the perfect setting for a relaxed and memorable island getaway.The spacious living room features ample seating, making it the ideal place
**New Bonus Room Off of the Pool and Updated Bathrooms!!**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
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