Hilton Head Rentals with Private Pool
Skip the crowds and enjoy a pool all to yourself with a private pool rental from Island Rentals of Hilton Head. These homes are built for families and groups who want to spread out, relax poolside, and make their own schedule without leaving the property.
Our private pool homes range from cozy retreats to spacious houses with room for the whole family, many just a short bike ride from the beach. Each rental includes 4 beach chairs, WiFi, and our Book Direct Savings, plus the responsive customer service and 24 hour on-call support you'll find across every Island Rentals of Hilton Head property.
Traveling with a large group or planning a multi-family trip? A private pool home is one of the best ways to keep everyone together. Explore the properties below, or browse our full Hilton Head vacation rentals collection and vacation homes if you're still comparing options.
22 properties available
Proudly hosted by Island Rentals of Hilton Head, this charming 3-bedroom, 2-bath private home in Sea Pines Resort offers the perfect blend of comfort, convenience, and relaxed coastal style. Thoughtfully designed with a spacious one-level layout, this home is ideal for families and groups looking to unwind without the hassle of stairs. The primary
Proudly hosted by Island Rentals of Hilton Head, 157 N. Sea Pines Drive is a stunning Sea Pines retreat perfectly positioned along the 17th tee of the Atlantic Dunes Golf Course. With tranquil lagoon views, a private pool, and an unbeatable central location, this home offers the ideal blend of relaxation, recreation, and classic Hilton Head Island
Proudly hosted by Island Rentals of Hilton Head. This exquisite Shipyard residence epitomizes the pinnacle of coastal luxury living, offering unrivaled access to pristine beaches, Hilton Head\'s vibrant shopping, and dining destinations, and the esteemed golf clubhouse, all within a leisurely stroll. The home boasts a captivating screened, partiall
Proudly hosted by Island Rentals of Hilton Head, this fabulous North Forest Beach home offers an unbeatable location just 180 steps from the beach—with no busy streets to cross. Considered one of the best values in North Forest Beach, this fully furnished six-bedroom retreat is perfect for gathering friends and family for a classic Hilton Head geta
Proudly hosted by Island Rentals of Hilton Head, 77 Lawton Road is a beautifully updated three-bedroom, three-and-a-half-bathroom home tucked away in the quiet Lawton Woods community of Sea Pines. Designed with vaulted ceilings and coastal-inspired décor, this spacious retreat offers a welcoming blend of comfort, style, and functionality—perfect fo
Proudly hosted by Island Rentals of Hilton Head, this beautifully updated coastal retreat offers the perfect combination of luxury, comfort, and location just fourth row from the ocean in North Forest Beach. Only a one-minute walk from Hilton Head\'s pristine shoreline, this spacious 4-bedroom, 2.5-bath home welcomes up to two dogs, making it an ex
Proudly hosted by Island Rentals of Hilton Head, 3 Nighthawk is a charming 4th-row ocean home ideally located in the highly desirable North Forest Beach area of Hilton Head Island. Just a one-minute walk to the beach, this pet-friendly retreat offers the perfect blend of comfort, convenience, and classic beachside living. With a private pool, fence
Welcome to the Sea Pines Escape at 39 Oak Court—an upscale 5-bedroom, 5.5 bathroom retreat in Hilton Head Island\'s exclusive Sea Pines Resort. This fully renovated luxury home offers the perfect blend of modern coastal design, spacious indoor comfort, and resort-style outdoor living—perfect for your next family vacation or group getaway!
Enjoy a
Proudly hosted by Island Rentals of Hilton Head, this stunning home offers the perfect retreat for families, friends, and even your furry companions. Just steps from the beach and only minutes from Coligny Plaza, you\'ll have easy access to Hilton Head\'s best dining, shopping, and entertainment. Whether you\'re planning a relaxing getaway or an ac
Proudly hosted by Island Rentals of Hilton Head, 15 Wagon Road offers the perfect combination of comfort, style, and location for your next Sea Pines getaway. Situated on a quiet street overlooking a peaceful lagoon and just a short five-minute walk from the beach, this beautifully renovated 4-bedroom, 3-bath home accommodates up to 12 guests and p
Proudly hosted by Island Rentals of Hilton Head, this newly renovated and tastefully furnished 3-bedroom home offers stunning golf course views and an unbeatable location within Sea Pines. Situated on peaceful Tupelo Street with minimal traffic, this retreat provides the perfect balance of tranquility and convenience—just a short bike ride from the
Featuring the newest Beach Oriented home in Sea Pines! Construction just completed in spring of 2025!
Escape to luxury in this stunning newly built coastal retreat in the heart of Sea Pines, just moments from the beach. Designed with elegance and comfort in mind, this spacious home offers thoughtfully designed living across three levels.
On the m
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