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.
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
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Golf Course Retreat in the Heart of Sea Pines3 Bedrooms | 2.5 Bathrooms | Sleeps 6 | Golf Course View | One-Level HomeWelcome to 78 Governors Road, a beautifully renovated, single-level home located on the Sea Pines Country Club golf course with views overlooking the 17th tee. Set in one of Sea Pines’ most desirable areas, this home offe
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.
Peaceful Coastal Living Near the Beach in Sea Pines 3 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
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
A Sea Pines Legacy Home for Longer Island Escapes5 Bedrooms | 5 Bathrooms | Sleeps 10 | Peaceful Backyard OasisLocated in the heart of Sea Pines on Hilton Head Island, The Hamilton is a beautifully furnished 5-bedroom, 5.5-bath legacy home available for extended monthly stays from November through April.With over 5,400 square feet of refined living
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Newly Renovated Pet-Friendly Villa Near Harbour Town at Stoney Creek1 Bedroom | 1 Bathroom | Sleeps 4Welcome to Stoney Creek Villa 249, your ultimate relaxing and comfortable getaway located in the heart of Harbourtown on Hilton Head Island. This newly renovated one-bedroom villa boasts modern and upscale furnishings, providing a stylish and inviti
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.
Charming Secluded Oasis in Sea Pines3 Bedrooms | 2 Bathrooms | Sleeps 8 | Dog FriendlyWelcome to our beautiful ocean-oriented vacation home, perfectly situated just inside the Sea Pines Ocean Gate on Hilton Head Island. This delightful 3-bedroom home, including a loft, offers a serene and tranquil setting surrounded by lush greenery. Immerse yourse
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.
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
HOT117
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.
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.
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
New Property
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.
Oceanfront Beach Oasis in Sea Pines5 Bedrooms | 4 Bathrooms | Sleeps 14 | Ocean Views | Backyard OasisWelcome to 33 Ruddy Turnstone, an exceptional oceanfront vacation home located in the prestigious Sea Pines resort of Hilton Head Island. This stunning 5-bedroom, 4 full bath, and 2 half bath beach house offers the perfect blend of modern eleg
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
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.
Scenic Harbour Town Villa in Sea Pines2 Bedrooms | 2 Bathrooms | Sleeps 4Wake up to one of the most recognizable views on Hilton Head Island. From this two-bedroom, two-bath villa at 1030 Caravel Court, the iconic Harbour Town Lighthouse stands just beyond your window—framed by yachts, calm harbor waters, and the lively charm of Harbour Town
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
