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.


Properties Available 51 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This 4-bedroom, 4.5-bathroom home is in the heart of Sea Pines Plantation. This cozy home features multiple living spaces throughout the home, making it perfect for large groups of friends and families. Relax and unwind by the pool and newly renovated deck or
2 Tupelo Drive Fairway Collection Icon
House -
$307.00 - $956.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 5 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This stunningly decorated 2-bedroom villa is just steps away from Harbourtown. The open-concept living space offers breathtaking views of the Calibogue Sound. Walking in on the first level, you are met with a spacious living room with comfy couches. Open to t
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Water View
729 Schooner Court
Villa - Pet Friendly
$154.00 - $858.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 4 guests
Rating 4.8 (14)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This spacious 3-bedroom, 2-bathroom top-floor Bluff villa is perfect for a larger family, with an open floorplan and one of the largest living spaces found in any Sea Pines villa. With six beds and room for up to two children on the sleeper sofa, this unit ha
1690 Bluff Villas
Villa -
$97.00 - $399.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (11)
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
5 Jessamine Place
House -
$287.00 - $1,112.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 5 (16)
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, and
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57 North Sea Pines Icone Collection Icon
House -
$370.00 - $1,432.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 5 (12)
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 5-minute bike ride to
Hot HOT 73
6 Gunnery Lane
House -
$269.00 - $865.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 5 (5)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This cozy villa has two spacious bedrooms and large closets and is minutes from Harbour Town. When you first walk in, the kitchen is open to the dining area and living room. The living room offers plenty of seating to relax after a day out in the sun. Heading
2334 Racquet Club
Villa -
$135.00 - $1,411.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 5 guests
Rating 5 (11)
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
2380 Lighthouse Tennis
Villa -
$135.00 - $500.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2538 Gleneagle Green is a pet-friendly Harbour Town villa with stunning views of Harbour Town Golf Course and is located just a short 5-minute walk to the shops and dining at Sea Pines Center, as well as the famed Harbour Town Marina! The open-concept floor
2538 Gleneagle Green Fairway Collection Icon
Villa - Pet Friendly
$135.00 - $1,199.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. With a scenic spot on the 11th hole, a private pool and spa to spend the day in, and spectacular views of the lagoon and golf course, this South Carolina home is the perfect vacation spot. Vaulted ceilings make this property feel comfortably spacious, which
38 Stoney Creek Road | Carolina Getaway Fairway Collection Icon
House -
$251.00 - $1,249.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (10)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This beautifully remodeled 3-bedroom home is very stylish, with a coastal cottage vibe throughout. The property features an open living, dining, and kitchen area that is fully equipped with top-of-the-line furnishings to provide all you need for a relaxing su
7 Hollyberry Lane
House - Pet Friendly
$165.00 - $519.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. "Fairway Palms" is a low-country gem. It is in a lovely private setting in Sea Pines, in the coveted Harbour Town neighborhood. The home is uniquely situated on the 8th fairway of Harbour Town Golf Links, surrounded by two beautiful lagoons. Expansive views w
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New Pictures
21 Heritage | Fairway Palms Fairway Collection Icon
House -
$500.00 - $1,317.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 5 (6)

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