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 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.

Sea Pines Community Guidelines

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Properties Available 43 properties available
Welcome to 30 Ruddy Turnstone! 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. There are lots of books to read; there is lots of seating on the sofas; a kitchen bar that seats 4 overlooks the kitchen
Hot HOT 108
30 Ruddy Turnstone | Ruddy Retreat
House - Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 6 baths
Guests 14 guests
Rating 4.8 (6)
Welcome to 6 Grey Widgeon! 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 huge windows allow plenty of natural sunlight to shine through
6 Grey Widgeon Icone Collection Icon
House -
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half baths
Guests 16 guests
Rating 4.8 (5)
Marsh view 2-story townhouse just steps to all that Harbour Town has to offer! Truly unique 1 bedroom with two entrances, separate laundry room, and powder room on the first floor. The 2-story ceiling in the living room allows plenty of afternoon natural light. There is great storage space under the staircase and a large storage closet in the hallw
273 Stoney Creek
Bedrooms 1 bedrooms
Bathrooms 1 baths
Half Bathrooms 1 half baths
Guests 2 guests
This amazing island getaway is nestled among the pines beside a lagoon on 1.9 acres in the heart of Sea Pines. This beach home offers beautiful high-end finishes in the huge eat-in kitchen and throughout, including the spacious dining room, living room, and first-floor master suite. The media room, bedrooms, and bathrooms are luxurious and comfort
5 Calibogue Cay
House - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half baths
Guests 10 guests
Rating 5 (1)
Welcome to 2 Tupelo Drive! 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 on the covered outside patio that has great views of the 3rd ho
2 Tupelo Drive Fairway Collection Icon
House -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half baths
Guests 12 guests
Rating 5 (5)
Welcome to this spacious and relaxing 3-bedroom home in the charming, gated community of Sea Pines. Open the door to experience a serene view of a private lagoon shaded by palm trees and live oaks dripping with Spanish moss. An abundance of natural sunlight streams in through the floor-to-ceiling windows. You will know you have arrived in the seren
35 Shell Ring
House -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 5 (1)
This gorgeous Sea Pines villa has been recently renovated and features golf and lagoon views. Walk in to an open-concept kitchen, dining, and living room. Relax on either of the comfortable couches in the living room and watch your favorite programs on the large flat-screen cable TV, or relax in the Carolina room at the rear of the villa, featuring
3 Lighthouse Road Villa Fairway Collection Icon
Villa Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Brand new to the rental market! New flooring, lighting, doors, furnishings, linens, art, and decor throughout! This decorator-designed Sea Pines home is ideal for families, friends, and making memories. As you open the coastal blue front door, you\'re met with a spacious, open-concept family and dining room. The living spaces are welcoming and com
Hot HOT 58
4 Indigo Lane
House -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (11)
Welcome to 3322 Lake Forest. 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 updated with granite countertops, white cabinets, and a stone backsp
3322 Lake Forest
Villa -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.7 (7)
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 everything you need. Attached to the great room, the Carolina room with a ping pong table i
Hot HOT 50
26 Forest Drive
House -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 6 guests
Rating 5 (4)
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 summer vacation with the whole family. This house comes with access to a neighborhood pool, t
Hot HOT 63
7 Hollyberry Lane
House - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (6)
5 Rice Lane is a renovated Sea Pines home with a private pool. This coastal home is perfect for vacationing. Be welcomed in by the living room, where you can relax and watch television or unwind with a great book. Heading through the home, the kitchen has ample space to cook a great meal for the family. It has an open layout to the dining room, whi
5 Rice Lane
House - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (1)

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