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, 7 Genoa Court is an extraordinary pet-friendly luxury retreat nestled in the heart of Sea Pines Resort, just moments from the iconic Harbour Town Marina. Thoughtfully designed to accommodate up to 16 guests, this elegant 6-bedroom, 6.5-bath residence offers sophisticated coastal living with premium a
Proudly hosted by Island Rentals of Hilton Head:
This striking Sea Pines home offers the perfect combination of comfort, style, and convenience in the heart of the Sea Pines Resort. Centrally located between the world-famous Harbour Town Yacht Basin and the Sea Pines Beach Club, guests can easily explore either destination with a short 10–15 minute
Proudly hosted by Island Rentals of Hilton Head, 25 Red Maple is where coastal charm meets modern comfort. Nestled at the end of a peaceful cul-de-sac in Sea Pines, this fully remodeled retreat offers 4 bedrooms and 3 bathrooms, making it perfect for families, groups, or multi-generational getaways. The spacious layout includes 3 Kings, 2 Twin-over
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, 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 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, 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, 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
6 Cannon Row, Sea Pines
Private Home, New Private Pool
Basic Features:
- 2121 sq. ft.
- 3 bed, 2 Bath
- 2 Kings, 2 Twins, 2 Bunk Beds
- TV/DVD player in living room
- Fireplace (For Decorative Purposes Only)
- Gas Grill
- Huge back deck with lagoon view
- WiFi
- 1 Hour free tennis daily at South Beach Racquet Club
- 1 Car pass into Sea Pines
- 4 F
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 incredible Sea Pines retreat has undergone extensive updates for 2025 and offers an exceptional setting for large families or groups vacationing together. Thoughtfully designed with both a five-bedroom main house and a two-bedroom attached guest house, the property comfortably sleeps up to fourt
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
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