All Vacation Rentals


Properties Available 99 properties available
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
353 Low Oak Woods is a pet-friendly 4 bedroom, 3.5 bathroom private West Beach vacation home offering tranquil fairway views and a small private pool just a 4-minute walk to Boardwalk 12. This spacious 3,430 sq ft Kiawah Island vacation home is laid out over two levels and comfortably accommodates up to 8 guests. On the first floor is the main liv
353 Low Oak Woods
House -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathroom 1 Half bath
Guests 8 guests
This stunning 1 bedroom, 1 bathroom Mariners Watch villa is nestled in the East Beach neighborhood of Kiawah Island, conveniently located near Night Heron Park and just a short 3-minute walk to the beach!The open plan living area is newly decorated with a comfortable L Shaped sectional sofa. There is a large desk in the living room that once pulled
4285 Mariners Watch Villa Woodland View
Villa -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
This spacious 3 bedroom, 2 bathroom Sparrow Pond Cottage accommodates up to 6 guests in comfort and style. A true home away from home, this Kiawah Island cottage boasts a screened porch, a furnished wraparound deck, a community pool, and coastal-inspired interiors.This Kiawah Island cottage is beautifully decorated with a spacious living area full
1031 Sparrow Cottage Woodland View
Cottage -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
4468 Windswept Villa is a stunning 1 bedroom, 1 bathroom villa located in the popular East Beach area of Kiawah, only steps from the ocean and minutes to Night Heron Park and world-class golf courses. This second-floor villa offers serene wooded Island views from inside and out. The open plan living area features a sofa sleeper, comfortable seatin
4468 Windswept Villa Woodland View
Villa -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Enjoy this well maintained first floor 2 bedroom, 2 bathroom Tennis Club Villa close to the beach, Night Heron Park, The Sanctuary and the award-winning Roy Barth Tennis facilities in East Beach, Kiawah Island. The beach is a short 6 minute walk or 2 minute bike ride away! This Tennis Club Villa has an open plan layout with lots of natural light a
4741 Tennis Club Villa Wooded View
Villa -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
This bright and beachy 3 bedroom, 2 bathroom Sparrow Pond Cottage accommodates up to 7 guests in comfort and style. A true home away from home, this Kiawah Island cottage boasts a large wraparound deck with a charcoal BBQ grill, an enclosed four-season Carolina room, an enlarged kitchen with Le Creuset pans, and a beautiful, blue-and-white interior
1023 Sparrow Pond Cottage Wooded View
Cottage -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
81 Surfsong Road is a 5 bedroom, 4.5 bathroom Kiawah Island vacation home with only a short walk down scenic Surfsong Rd to the beach access. This spacious home boasts 3,576 sq ft of beautifully appointed interiors, exceptional outdoor living and a recently added pool and spa with long views down Canvasback Pond. The large back deck has beautiful
81 Surfsong Road
House -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathroom 1 Half bath
Guests 10 guests
23 Turtle Beach Lane is a stunning 3 bedroom, 3 bathroom Kiawah Island vacation home in the popular Atlantic Beach neighborhood of East Beach Village. This spacious family home offers an expansive screened porch, a private outdoor deck overlooking the lagoon, tranquil golf views, community pool access located just across the street, and convenient
23 Turtle Beach Lane
House -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
This stunning 3 bedroom, 3 bathroom Kiawah Island cottage is located in the West Beach area and has been newly remodeled in Spring 2023! Enjoy island style living with a wraparound porch, natural gas grill for BBQs, access to a secluded community pool, and a brand-new outdoor shower just off the steps to quickly rinse off after a day on the beach,
1063 Sparrow Pond Cottage Woodland View
Cottage -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
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
122 Bufflehead Drive
House -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathroom 1 Half bath
Guests 10 guests
4341 Windswept is a stunning lakeside villa located directly across from beach access in Kiawah Island’s East Beach neighborhood. This spacious 2 bedroom, 2.5 bathroom villa offers designer interiors with all the comforts of home, a private deck with island views, and a convenient location just a quick walk from the beach and the island’s top attra
4341 Windswept Lakeside Woodland View
Villa -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathroom 1 Half bath
Guests 5 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.