Sea Pines
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 16 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.
45 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This Sea Pines home is nestled on a quiet street and places you only minutes away from Harbour Town and the sandy beaches!
Upon entry, you walk into the sitting room, which has plenty of comfortable seating around the cozy brick fireplace (not for guest use)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
3 Bedroom Villa in Harbour Town Area, Newly Renovated, and Golf View. Gorgeous renovations in 2020 make this villa the right choice for you. As you enter, you are greeted with a two-story, open, and airy space. This open-concept living, dining, and kitchen ar
2371 Racquet Club
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 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.
This 2 bedroom, 2-bath Beachside Tennis villa has panoramic views of Calibogue Sound. Located in the South Beach area of Sea Pines on the first floor of a five-story building, just steps to the pool and beach,
When entering the villa, you will find the mast
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.
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.
This breath-taking 4th-row home is one of a kind and has everything you need and more for your next Hilton Head vacation. The great room is spacious and is sure to keep guests feeling right at home with its stylish but cozy furnishings! Soaring ceilings and h
6 Grey Widgeon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Single-level home with 3 bedrooms and a short walk to the beach! Enjoy close access to the beach in this fully renovated coastal chic ranch home with a hot tub and private outdoor shower! All-new kitchens, baths, furniture, and more ensure a comfortable and r
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 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.
This 7,500-square-foot beachfront home features a private, in-ground pool with a spa and a patio overlooking the Atlantic Ocean. With private beach access, this home is perfect for those long beach days! The kitchen is equipped with stainless steel appliances
23 Black Skimmer
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