Sea Pines Resort on Hilton Head Island blends Lowcountry charm with family-friendly amenities, outdoor adventure, and a laid-back coastal lifestyle. At Hilton Head Properties R&R, we offer a hand-picked selection of 21 vacation homes and villas in this iconic community—each thoughtfully maintained and located near Sea Pines’ top attractions. From spacious interiors and screened porches to access to community pools and bike trails, our rentals make it easy to relax and recharge.
Guests love being close to the Sea Pines Beach Club, Harbour Town Yacht Basin, and scenic golf courses like Harbour Town Golf Links and Heron Point. The resort’s miles of leisure paths and natural preserves invite quiet mornings and active afternoons alike. Whether you’re planning a beach getaway, a golf retreat, or a family adventure, our Sea Pines vacation rentals provide a welcoming home base in one of Hilton Head Island’s most beloved neighborhoods.
Charming Lagoon Home in Sea Pines2 Bedrooms | 2 Bathrooms | Sleeps 6 | Pet FriendlyWelcome to your newly remodeled oasis at 57 Night Heron, nestled just inside the exclusive Sea Pines gated community. This charming home is perfectly positioned for a beach getaway, with easy access to the pristine shores just a short walk away and the community pool
Family Home Nestled in the Heart of Sea Pines5 Bedrooms | 4 Bathrooms | Sleeps 12 | Private PoolWelcome to your ultimate vacation home at 25 Willow Oak Road West, nestled in the heart of Sea Pines on Hilton Head Island.This stunning property offers the perfect retreat for those seeking a memorable and luxurious getaway. Situated just a short walk a
Spacious Dog Friendly Home Located in Sea Pines4 Bedrooms | 3.5 Bathrooms | Sleeps 10 | Private Pool & SpaLooking for a prime location for your next vacation? Look no further than 16 Duck Hawk, located in the heart of Sea Pines on Hilton Head Island.Upon entering the home, you'll be greeted with an expansive living room that transitio
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
3-Bedroom Heritage Villa Near Harbour Town with Community Pool3 Bedrooms | 3 Bathrooms | Sleeps 9 | Community Pool | Near Harbour Town | NEW PHOTOS COMING SOONWelcome to 2209 Heritage Villas, a spacious three-bedroom, three-bath townhome located in the heart of Sea Pines on Hilton Head Island. With the Heritage Villas community pool just
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Coastal Elegance with Iconic Harbour Town Golf Views3 Bedrooms | 3 Bathrooms | Sleeps 8 | Community PoolThis exceptional coastal retreat is truly special, offering an open, airy floor plan filled with natural light and panoramic views of Harbour Town's famed golf holes - the #6 and #7 fairways, along with inviting floor plan designed for relaxe
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New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Cozy Cutter Court Villa in Sea Pines2 Bedrooms | 2 Bathrooms | Sleeps 5 | Serene RetreatWelcome to 911 Cutter Court, a second-floor villa that puts you right in the heart of Harbour Town. Overlooking the Harbour Town Golf Links Clubhouse, this two-bedroom, two-bathroom retreat offers a front-row seat to one of Hilton Head’s most iconic settin
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New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Upgraded Lagoon Villa by South Beach in Sea Pines3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet FriendlyWelcome to 1587 Lagoon Villa—an upgraded 3-bedroom, single-level retreat in the heart of Sea Pines, just a short stroll to the beach, Salty Dog Marina, and pickleball courts. Recently remodeled from top to bottom with high-end finishes, this vil
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Refined Coastal Living in Sea Pines4 Bedrooms | 4 Bathrooms | Sleeps 12 | Backyard Oasis with Private PoolWelcome to a truly exceptional vacation home in Sea Pines—a rare blend of timeless elegance and modern comfort, now part of the Hilton Head Properties R & R rental collection. This single-level residence has been exquisitely reim
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Peaceful Coastal Living Near the Beach in Sea Pines 2 Bedrooms | 2 Bathrooms | Sleeps 6 | Community Pool | Pet Friendly Tucked among the pines and just a quick walk from the beach, 66 Night Heron offers relaxed island living in one of Sea Pines’ most convenient locations. This freestanding home blends privacy with easy acc
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New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Newly Remodeled Villa Near Harbour Town at Stoney Creek1 Bedroom | 1 Bathroom | Sleeps 6Class, comfort, and a touch of prestige await at this beautifully remodeled one-bedroom, one-and-a-half-bath townhome in the sought-after Stoney Creek neighborhood of Sea Pines. This charming loft-style retreat features soaring cathedral ceilings, oversized wind
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New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Charming Lagoon-View Retreat in Sea Pines2 Bedrooms | 2 Bathrooms | Sleeps 6 | Dog FriendlyWelcome to your own private oasis in Sea Pines, Hilton Head Island. This charming 2-bedroom vacation home is nestled in a serene wooded setting, just inside the Sea Pines Ocean Gate. Offering a perfect blend of privacy and convenience, this home provides an i
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Luxurious Willow Oak Home in Sea Pines4 Bedrooms | 4.5 Bathrooms | Sleeps 12 | Private Pool & SpaWelcome to your luxurious vacation retreat nestled in prestigious Sea Pines. This exquisite vacation home offers the perfect blend of elegance, comfort, and convenience for your getaway. As you enter the home, you'll be greeted by an inviti
