All Vacation Rentals


Properties Available 91 properties available
Tucked away in the trees behind the second gate on Kiawah Island is this luxury 4 bedroom, 3.5 bathroom Vanderhorst Plantation vacation home with stylish, spacious interiors, a private elevator, tranquil outdoor spaces with wooded views, and all the comforts of home for an exceptional stay on Kiawah Island. You’re welcomed to your Kiawah retreat
74 Governors Drive
House -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathroom 1 Half bath
Guests 10 guests
19 Surfsong is a spacious 5 bedroom, 5.5 bathroom private vacation home in the Vanderhorst Plantation on Kiawah Island. This home offers 4,850 sq. ft of beautifully decorated interiors and an expansive private deck with a private pool overlooking Canvasback Lagoon. The brand-new pool, completed in December 2024, offers a spacious 15'x26' swimming a
19 Surfsong Road
House -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathroom 1 Half bath
Guests 12 guests
99 Surfscoter Lane is a welcoming 3 bedroom, 2 bathroom private vacation home in the popular West Beach neighborhood, just a 3 minute walk to the beach and a short bike ride to Kiawah Island's dining, shopping and family-friendly island activities. This spacious 1,500 sq ft Kiawah home is a great option for a single family looking to have more spac
99 Surfscoter Lane
House -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
2476 Shipwatch is a 1 bedroom, 1 bathroom oceanfront villa in the popular West Beach neighborhood with inviting interiors, sweeping ocean views and beach access directly from the building to Kiawah Island’s miles of pristine beaches. This oceanfront villa is well-appointed with an open layout offering wonderful morning sun and natural light throu
2476 Shipwatch Oceanfront Villa
Villa -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
2273 Shipwatch is a stunning second floor 1 bedroom, 1 bathroom oceanside villa located in the heart of Kiawah Island’s West Beach neighborhood. This Shipwatch villa offers ocean views from the private deck as well as convenient access to the beach and the island’s top attractions. The living area is flooded with natural light and ocean views from
2273 Shipwatch Oceanside Villa
Villa -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
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
193 Ryder Cup
House - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
This Kiawah Exclusives home rental located in beautiful Vanderhorst Plantation overlooks the 4th hole of Turtle Point Golf Course. This 8 bedroom, 6.5 bathroom vacation home offers 4,300 sq ft of living space for large groups up to 18, a gourmet kitchen and an open deck with brand new furniture overlooking the golf course and your private pool! Th
230 Glen Abbey
House -
Bedrooms 8 bedrooms
Bathrooms 6 baths
Half Bathroom 1 Half bath
Guests 18 guests
This 2nd floor, 2 bedroom, 2 bathroom oceanfront Windswept condo is the perfect retreat for your next Kiawah Island vacation with direct ocean views from the living area and master bedroom and easy access to the beach from the building! This spacious Windswept villa is well-appointed with comfortable furnishings, a flat screen TV and tile floors.
5110 Windswept Oceanfront Villa
Villa -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
This charming 4 bedroom, 4 bathroom Kiawah Island vacation home is located in popular West Beach one block from the beach, nature/biking trails and the West Beach Tennis Center. This spacious home offers a large screened porch, gas grill and outdoor shower, fun ping pong table and a true home-away-from-home for your Kiawah Island vacation. Offerin
119 Surfscoter Lane
House -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 9 guests
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
305 Ocean Oaks
House -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathroom 1 Half bath
Guests 8 guests
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
4409 Windswept Oceanside Villa
Villa -
Bedrooms 1 bedrooms
Bathrooms 2 baths
Guests 4 guests
411 Ocean Oaks is a charming 5 bedroom, 4.5 bathroom Vanderhorst Plantation rental home located in the desirable back island neighborhood of Ocean Oaks. This plantation style home offers 3,580 sq ft of stylish and spacious interiors with 2 primary bedrooms, a screened porch and scenic courtyard with lagoon views, and easy access to Kiawah Island’s
411 Ocean Oaks
House -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathroom 1 Half bath
Guests 12 guests

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Kiawah Island Vacation Rental FAQs:

What are the top activities to enjoy on Kiawah Island?

Kiawah Island is a perfect playground for those who truly love the great outdoors. It starts with Kiawah’s ten miles of pristine beach, ideal for swimming, collecting seashells, or relaxing with a good book.

For the golfers, you’re in luck. Five of the island’s courses are ranked some of the best in the country. The Ocean Course, in particular, has an esteemed status from hosting PGA legends and iconic tournaments.

Want to stay closer to nature? Hop on a bike or lace up your shoes, as trails weave through forests and marshland where you might spot deer, herons, or even a gator or two. If you prefer your thrills on the water, you can paddle through tidal reeks in a kayak or on a paddleboard for an up-close view of the island’s wild side.

From tennis courts to guided tours, every detail is thoughtfully designed for you to explore. So whether you’re chasing adrenaline or serenity, Kiawah has you covered.

 

When is the best time to visit Kiawah Island?

Each season brings its unique charm, and it all depends on the experience you’re after. Spring and fall are fan favorites, with mild temperatures, fewer crowds, and perfect days for golfing or getting lost in nature.

Summer brings the heat and the crowds, making it the busiest season. However, it’s also the best time for experiencing long and sunny days on the beach. Classic island buzz.

If you’re drawn to peace and quiet, winter is the season for you. Cooler days make for dreamy walks and slow mornings, plus often a more budget-friendly time to visit. No matter when you choose to visit, it’s all about finding what suits you between the weather, the crowds, and the cost.

 

How do I get to Kiawah Island and move around once there?

Kiawah Island is about 30 miles away from Charleston International Airport. Upon arrival at Charleston International, it’s a scenic 45-minute drive to the island, where you’ll pass a gated entrance. There’s no public transit, so make sure to plan for either renting a car or taking the shuttle.

Once you’re on Kiawah, having your own set of wheels is ideal, especially if you’re planning on getting around and exploring. The island's vast bike trails make it easy to rent one and cruise trails that link beaches, golf courses, and restaurants. Walking works just fine for short hops in central areas.

To maximize the full island experience, it is recommended to have some kind of ride to keep your visit to Kiawah Island smooth and simple.

 

What is the weather like on Kiawah Island throughout the year?

Hitting temperature highs in the 80’s and 90’s, expect a hot and humid summer due to Kiawah Island’s subtropical weather. Expect sunshine with a side of afternoon storms on your beach day visits during this season.

Winter, on the other hand, tends to be fairly mild. Daytime temps are in the 50’s and 60’s, and nights rarely dip near freezing. This time of the year is ideal for golf, long walks, or hanging out and enjoying the quiet season.

As for spring and fall, highs reach the 70’s with lower humidity and light rainfall keeps the island lush and vibrant. These seasons are a perfect time for a wide variety of island activities.

Packing for the season is a must. Prepare swimsuits in the summer and light jackets for the rest of the year.

 

Where should I stay on Kiawah Island for the best experience?

If you’re craving a full-on luxury experience, the Kiawah Island Golf Resort offers the service you’re looking for. They offer deluxe restaurants, bars, and experiences all within a short distance away from the golf course and the beach.

Vacation homes and condos offer more space and privacy. There’s plenty available across the island, with many featuring ocean views, back-deck sunsets, or trail access right outside your doorstep. The ideal choice for families or larger groups.

Choosing your beach getaway is crucial to having the best Kiawah Island experience. Staying near the Sanctuary leans more towards the classic, high-end hotel atmosphere, while rentals around the east and west ends of the island are more for seclusion or staying close to your favorite course.

It all comes down to what you want your vacation to be: the resort treatment, beachfront living, or a simple tranquility.