All Vacation Rentals


Properties Available 98 properties available
4300 Windswept Villas is new to Kiawah Exclusives and offers a truly opulent oceanfront experience on Kiawah Island. This 3 bedroom, 3 bathroom oceanfront villa boasts a prime first floor location with stunning ocean views, designer interiors throughout and upscale amenities for a luxury Kiawah Island vacation, only steps from the beach! Enter in
4300 Windswept Oceanfront Villa
Villa -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
4906 Turtle Point is a luxury pet-friendly villa nestled in the quiet East Beach neighborhood of Kiawah Island, offering 2 bedrooms and 2 bathrooms, spacious interiors with high-end furnishings, an expansive screened porch for alfresco dining, a private deck with tranquil island views, and close proximity to the beach just a short walk away!This sp
4906 Turtle Point Villa
Villa -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Nestled below a canopy of live oaks, this beautifully maintained 5 bedroom, 5.5 bathroom Vanderhorst Plantation home is the perfect retreat for your next vacation and less than a minute to Kiawah Island’s 10 mile stretch of pristine beaches. This spacious Kiawah vacation home is open and bright and offers 3,550 sq ft of exceptional living space c
87 Jackstay Court
House -
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathroom 1 Half bath
Guests 10 guests
Welcome to 77 Forestay, your home away from home on Kiawah Island in a prime wooded setting just across the street from the beach!! This gorgeous 4,436 sq ft vacation home boasts 6 large bedrooms, 4.5 bathrooms, a private pool and everything you need to make your vacation a breeze. If you’re searching for houses for rent on Kiawah for a large famil
77 Forestay
Bedrooms 6 bedrooms
Bathrooms 4 baths
Half Bathroom 1 Half bath
Guests 12 guests
Enjoy your Kiawah Island vacation in a 3 bedroom, 3 bathroom Kiawah villa located on the 2nd floor, off the 17th fairway of the Turtle Point golf course. A short 30-minute drive from historic Charleston, a brief drive to 5 championship golf courses and a simple 7 minute walk from the beach and the Sanctuary Hotel, this premier villa is perfectly si
4974 Turtle Point Villa Golf View
Villa -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
4560 Parkside Villa is a newly updated and tastefully furnished 3 bedroom, 3 bathroom Kiawah Island villa located in the popular East Beach Village area with amazing lagoon views, a sunny screened porch, and a private dock. This villa is in the heart of Kiawah Island only minutes to the beach, Night Heron Park and world-class golf. The villa is sp
4560 Parkside Villa Lagoon View
Villa -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 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
21 Surfsong is a single story 3 Bedroom, 3 Bathroom private vacation home in the Vanderhorst Plantation on Kiawah Island. This home offers 3,100 sq feet of classic interiors and an expansive private deck overlooking Canvasback Lagoon for sunning, entertaining or alfresco BBQ dining, only a short 2-minute stroll from the beach! The bright and elega
21 Surfsong
House -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
4176 Night Heron is an inviting 1,300 sq ft vacation rental cottage in the heart of Kiawah Island, close to Night Heron Park, a short bike ride or scenic walk to the beach, and centrally located to enjoy the best shopping, dining and activities on Kiawah Island. This Cottage has 3 bedrooms and accommodates up to 6 guests. This spacious Night Hero
4176 Night Heron Cottage Woodland View
Cottage -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
4303 Windswept Villas is a 1 bedroom, 1 bathroom first floor oceanfront villa in East Beach Village, only steps to the miles of pristine beaches of Kiawah Island. This elegant first-floor Windswept villa features ocean views from the living room - soak up some sun on the deck, dine al fresco on the covered porch, or just curl up on the couch for a
4303 Windswept Oceanfront Villa
Villa -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
1066 Sparrow Pond is a 3 bedroom, 2.5 bathroom beach cottage in West Beach Village Kiawah with exterior deck, modern bathrooms and a fresh outdoor shower to end your day at the neighborhood swimming pool or the beach, only a short 5 minute walk away. This elegant Kiawah Island cottage is open and spacious with a comfortable living area and flat s
1066 Sparrow Pond Cottage Woodland View
Cottage -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathroom 1 Half bath
Guests 7 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

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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.