2026 Sale Early Access
Our Annual Sale is back! Beginning 01/05/2026, book your 2026 vacation at our lowest rates of the year. Save 20% on 4+ night stays when you book by 02/03/2026 and use code SALE2026 at checkout. Must stay by 12/31/2026.
75 properties available
Experience the ultimate in luxury and breathtaking views from the comfort of this stunning 4 bedroom, 4.5 bathroom Vanderhorst Plantation luxury vacation home. Nestled on the shores of Bufflehead Pond and alongside the fairways of the Osprey Golf Course, 122 Bufflehead comfortably accommodates up to 10 guests in a spacious and exceptionally maintai
328 Moon Tide Lane is a secluded, private retreat on 2.36-acres of Kiawah riverfront. This luxury 5 bedroom, 4.5 bathroom Kiawah Island vacation rental boasts 4,636 sq of designer interiors with, wonderful outdoor spaces with a private pool with large spa, expansive marsh views from nearly every room and breathtaking sunset views! Featuring an open
594 Piping Plover is a custom 4 bedroom, 4.5 bathroom Vanderhorst Plantation vacation home overlooking the 12th fairway of Osprey Point Golf Course and Bufflehead Pond. This spacious 4,056 sq ft private home boasts luxurious living spaces with a private elevator, a large deck and BBQ grill overlooking the fairways, a tranquil screened porch and a s
4409 Windswept Villas is a beautifully renovated 1 bedroom, 2 bathroom oceanfront Kiawah Island villa with a private deck leading directly to a beach path. Located in East Beach, you’re conveniently located to the best of Kiawah Island. The open plan living area is elegantly decorated with a sleeper sofa, decorative fireplace and flat screen TV f
Experience the beauty of 4 Airy Hall, a luxurious vacation home featuring 4 spacious bedrooms and 4.5 bathrooms, located in the exclusive Vanderhorst Plantation of Kiawah Island. This stunning property provides breathtaking natural views and includes a covered outdoor dining area as well as a private pool with a sunning area, making it perfect for
192 Ryder Cup is located in the sought after Vanderhorst community. This spacious 4 bedroom, 3 bathroom Kiawah Island vacation home overlooks one of the most captivating lagoons on the island and features a sparkling, private pool and easy beach access! Double doors open to the foyer which leads to the airy living room featuring hardwood floors, a
4809 Turtle Cove is a first-floor villa that boasts stunning lagoon views and is located only a short walk from The Sanctuary, Night Heron Park, Turtle Point Golf Club, the Tennis Center, and miles of pristine Kiawah Island beach.The living area offers natural light through double sliding glass doors, comfortable seating with a pull-out sofa bed, a
130 Turnberry Drive is a spacious 3 bedroom, 3 bath Vanderhorst Plantation vacation home offering expansive views of the Turtle Point Golf Course. This home has been completely renovated in 2021 with all new furnishings and your luxury Kiawah Island family vacation in mind. This home offers approximately 2,800 sq feet of luxurious comfort with a
363 Red Bay is a 4 bedroom, 3.5 bathroom Kiawah Island vacation home nestled in a quiet cul de sac overlooking a tranquil lagoon and the lush fairways of the Cougar Point Golf Course, only a 4 minute walk to the beach! Enter through the front door and you will immediately notice the well-thought furnishings and appointments. An open floor plan an
This private home offers exceptional indoor and outdoor living spaces with 4 bedrooms, 4 bathrooms. Located on a quiet cul-de-sac behind the second security gate in the Vanderhorst Plantation, this vacation rental overlooks a scenic lagoon teaming with wildlife and is just a 5 minute walk to the pristine beaches of Kiawah Island! On entry, the foye
*1031 Sparrow Pond Cottage has just undergone a renovation and expansion completed in May 2026. A 3rd full bath as been added and total interior square footage has gone up from 1067 to 1207 sq ft. .*This spacious 3 bedroom, 3 bathroom Sparrow Pond Cottage accommodates up to 6 guests in comfort and style. A true home away from home, this Kiawah Isl
305 Ocean Oaks is a beautifully appointed 4 bedroom, 4.5 bathroom Vanderhorst Plantation vacation home offering extreme privacy in the scenic Ocean Oaks neighborhood. This serene home boasts 3,600 sq ft of exceptional living space, a screened porch and deck with tranquil marsh views and easy access, just a 6-7 minute walk, to Kiawah Island’s pristi
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