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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46 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautiful villa is perfect for relaxing and unwinding. The spacious great room features vaulted ceilings and unbelievable nature and water views.
Walk into this beautifully decorated villa and be greeted by lagoon views. The kitchen was recently update
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.
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 beautifully renovated 3-bedroom, 2.5-bath home has an open floor plan. The living room has ample room to relax and watch TV on the large flat screen; the dining area seats six people; and the kitchen has stainless steel appliances, granite counters, and
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
The property is situated among the palmettos and oak trees of Hilton Head Island and steps away from the Atlantic Ocean. The lapping of the waves on the beach of this oceanfront home will put you to sleep, while the bedrooms on the street side of the house ge
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.
5 Jessamine Place is only a 10-minute walk to the best beach on Hilton Head Island!
This ranch-style cottage home is newly renovated and beautifully furnished. It offers four bedrooms and four bathrooms to comfortably host up to 13 guests. Nestled on a quie
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property will be undergoing construction and unavailable for rental during 2026. If you have any questions, please reach out to us at or call
This beautifully upgraded vacation home combines sophisticated design, high-end finishes, and abundant natur
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Welcome to a beautifully designed retreat where warm natural light, effortless flow, and thoughtful comforts create an unforgettable stay. From the moment you walk in, the home opens into a bright and spacious layout that invites relaxation.
To the left of t
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
6 Gunnery is a spacious and inviting home ideally located in the heart of Sea Pines. Nestled halfway between Harbour Town and South Beach Marina, this property offers the perfect combination of convenience and tranquility. Enjoy an easy 10-minute walk or 5-mi
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
With beautiful craftsmanship throughout the well-appointed house. The ground level has a newly refinished pine floor and an open-plan design, with the large kitchen overlooking the cozy living room equipped with a comfortable sleeper sofa. There are lots of b
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
A charming first-floor villa with a walkout balcony offering breathtaking views of the golf course. Nestled in the heart of Sea Pines, this delightful retreat combines comfort and convenience, making it the perfect getaway for golfers and vacationers alike.
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