Sea Pines Vacation Rentals
Stay at our Sea Pines vacation rentals on Hilton Head Island. We offer a wide range of Sea Pines rentals that can accommodate anywhere from 4 to 28 guests. Explore the beautiful surrounding area with nearby access to miles of beautiful beaches and three golf courses including the Harbour Town Golf Links, a famed PGA Tour stop. Local highlights include the Sea Pines Beach Club which offers exquisite oceanfront dining and the Lawton Stables where you can enjoy a pony ride or visit the animals. Conveniently access water activities at South Beach Marina and Harbourtown Yacht Basin. Explore Sea Pines on miles upon miles of pristine bike paths. Play tennis at the world-famous Smith Stearns Academy. Take in beautiful sunset views from atop the world-famous Harbourtown Lighthouse.
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45 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy the unbeatable convenience of this home\'s location, offering effortless access to the very best of Hilton Head. Just minutes from the Sea Pines gates, you\'ll find it easy to explore iconic destinations like Harbour Town, Coligny Plaza, and the island\
150 Otter Road
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Thoughtfully refreshed and beautifully appointed, this 4-bedroom, 4.5-bath home in the heart of Sea Pines Plantation offers inviting coastal comfort with multiple gathering spaces, serene golf-course views, and a renovated pool deck perfect for relaxing days
2 Tupelo Drive
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautiful home is only steps away from the beach! Simply a lovely second-row home that invites you to come inside and enjoy. After a walk on the beach only steps from the home, relax by the pool, enjoy lunch and a nap on the deck, or sit by the fire pit
11 Grey Widgeon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Looking for the perfect vacation retreat? You\'ve come to the right spot!
This home is completely renovated! The inside of the home has new floors, new light fixtures, a new stairway, a newly updated kitchen with stainless appliances, a new laundry room, an
57 North Sea Pines
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely remodeled Sea Pines home sits on the 11th fairway and 15th green of the Harbour Town Golf Course!
With 5 bedrooms and 6 bathrooms, this sunlight-filled home can host up to 14 guests comfortably. As you enter the home, you are met with an extr
100 Baynard Cove
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2390 Lighthouse Tennis Villa invites you to experience the Sea Pines Community on Hilton Head Island. In addition to its premier location surrounded by beautiful scenery, this well-appointed villa is an exceptional getaway retreat. From Harbour Town Marina to
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Welcome to this inviting four-bedroom, three-bathroom home that combines bright open spaces with thoughtful design.
As you enter, you are welcomed into a light-filled interior. To the left of the entryway is the dining room, a warm and inviting space for mea
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home has been freshly updated with brand new exterior paint, kitchen countertops, renovated bedrooms and bathrooms, a new grill, and more exciting upgrades throughout! Photos have been updated to reflect these updates as of February 2026.
This pet-frien
36 Red Oak
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Please Note: Exterior improvement work will be taking place at Lighthouse Road Villas beginning the week of 4/20/2026. Work will include tree removal, driveway resurfacing, new sidewalk installation, electrical updates, and landscaping. Tree removal will begi
3 Lighthouse Road Villa
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Tucked away on a quiet cul-de-sac in the heart of Sea Pines, 28 Battery Road is a delightful single-level retreat designed for effortless coastal living.This charming home offers a thoughtful layout, inviting gathering spaces, and a serene outdoor oasis, maki
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably.
The first floor features a very open floor plan that offers easy access between the multiple living
2 Royal Tern
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 3rd-floor villa is recently updated and places you just minutes outside of the world-famous Harbour Town. With 2 bedrooms and 2 bathrooms, this Sea Pines villa can sleep up to 4 people comfortably. The living room is illuminated with natural light and ha
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