Book Holiday Homes in Kiawah Island

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Featured Holiday Homes in Kiawah Island

Serene and Private Villa, Close to Beach

Serene and Private Villa, Close to Beach

Kiawah Island
With a stay at this vacation home in Kiawah Island, you'll be by the sea, just a 2-minute walk from Kiawah Island Beach and 7 minutes by foot from Night Heron ...
Serene and Private Villa, Close to Beach
New Listing: Luxurious Home with Pool and Guest House on Kiawah

New Listing: Luxurious Home with Pool and Guest House on Kiawah

Kiawah Island
With a stay at this vacation home in Kiawah Island (Vanderhorst Plantation), you'll be a 4-minute drive from Kiawah Island Beach and 9 minutes from Osprey Point ...
New Listing: Luxurious Home with Pool and Guest House on Kiawah
Scenic view cottage w/ Free Wifi - just a short walk to the beach & park

Scenic view cottage w/ Free Wifi - just a short walk to the beach & park

Kiawah Island
With a stay at this vacation home in Kiawah Island, you'll be by the sea, just a 3-minute walk from Night Heron Park and 12 minutes by foot from Kiawah Island ...
Scenic view cottage w/ Free Wifi - just a short walk to the beach & park
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Spectacular Oceanfront Kiawah Home With Pool And Private Boardwalk To Beach

Spectacular Oceanfront Kiawah Home With Pool And Private Boardwalk To Beach

Kiawah Island
With a stay at this vacation home in Kiawah Island (Vanderhorst Plantation), you'll be a 1-minute drive from Kiawah Island Beach and 9 minutes from Osprey Point ...
Spectacular Oceanfront Kiawah Home With Pool And Private Boardwalk To Beach
Best BEACHFRONT Kiawah Rates! Pup Friendly, Cozy Home. NOW AVAIL 7/5-12/25

Best BEACHFRONT Kiawah Rates! Pup Friendly, Cozy Home. NOW AVAIL 7/5-12/25

Kiawah Island
With a stay at this vacation home in Kiawah Island (West Beach), you'll be steps from Kiawah Island Beach and a 5-minute drive from Osprey Point.
Best BEACHFRONT Kiawah Rates! Pup Friendly, Cozy Home. NOW AVAIL 7/5-12/25
BOOKING SMOKING HOT 2025 DEALS NOW!

BOOKING SMOKING HOT 2025 DEALS NOW!

Johns Island
With a stay at this vacation home in Kiawah Island (Vanderhorst Plantation), you'll be within a 5-minute drive of Kiawah Island Beach and Osprey Point Golf ...
BOOKING SMOKING HOT 2025 DEALS NOW!
Gorgeous Natural Light, Vaulted Ceilings & Fairway Views.  Back Deck & Screened Porch.

Gorgeous Natural Light, Vaulted Ceilings & Fairway Views. Back Deck & Screened Porch.

Kiawah Island
With a stay at this vacation home in Kiawah Island (Vanderhorst Plantation), you'll be within a 10-minute drive of Kiawah Island Beach and Osprey Point Golf ...
Gorgeous Natural Light, Vaulted Ceilings & Fairway Views. Back Deck & Screened Porch.
Beautiful Oceanfront Home, Amazing Ocean and Golf Course Views; Community Pool!

Beautiful Oceanfront Home, Amazing Ocean and Golf Course Views; Community Pool!

Kiawah Island
A stay at this vacation home places you in the heart of Kiawah Island, steps from Kiawah Island Beach and 7 minutes by foot from Turtle Point Golf Course.
Beautiful Oceanfront Home, Amazing Ocean and Golf Course Views; Community Pool!
Light and airy, central, golf location

Light and airy, central, golf location

Kiawah Island
With a stay at this vacation home in Kiawah Island (West Beach), you'll be within a 10-minute walk of Kiawah Island Beach and Osprey Point.
Light and airy, central, golf location
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Kiawah Island Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Kiawah Island vacation homes are the perfect way for you to wing it.

Holiday houses in Kiawah Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Kiawah Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Kiawah Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Kiawah Island with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Kiawah Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Kiawah Island Holiday Homes essential information

Accommodation
354 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Serene and Private Villa, Close to Beach, New Listing: Luxurious Home with Pool and Guest House on Kiawah, Scenic view cottage w/ Free Wifi - just a short walk to the beach & park, Spectacular Oceanfront Kiawah Home With Pool And Private Boardwalk To Beach, Best BEACHFRONT Kiawah Rates! Pup Friendly, Cozy Home. NOW AVAIL 7/5-12/25, BOOKING SMOKING HOT 2025 DEALS NOW!, Gorgeous Natural Light, Vaulted Ceilings & Fairway Views. Back Deck & Screened Porch., Beautiful Oceanfront Home, Amazing Ocean and Golf Course Views; Community Pool!, Light and airy, central, golf location

Top trending hotels in Kiawah Island

The Sanctuary at Kiawah Island Golf Resort

The Sanctuary at Kiawah Island Golf Resort

5 out of 5
1 Sanctuary Beach Drive, Kiawah Island, SC
With a stay at The Sanctuary at Kiawah Island Golf Resort in Kiawah Island (East Beach), you'll be steps from Kiawah Island Beach and a 1-minute drive from Turtle ...
The Sanctuary at Kiawah Island Golf Resort
Charleston Kiawah Island/Andell Inn

Charleston Kiawah Island/Andell Inn

3.5 out of 5
300 Farm Lake View Road, Kiawah Island, SC
Fully refundableReserve now, pay when you stay
Located in Kiawah Island, Charleston Kiawah Island/Andell Inn is next to a golf course, a 3-minute walk from Freshfields Village and 13 minutes by foot from ...
Charleston Kiawah Island/Andell Inn
Cottage w/ On-Site Golf, Shared Pool, & Beautiful Inlet Views - Near the Beach

Cottage w/ On-Site Golf, Shared Pool, & Beautiful Inlet Views - Near the Beach

Kiawah Island
Located in Kiawah Island (West Beach), this cottage is within a 5-minute drive of Kiawah Beachwalker Park and Cougar Point Golf Course.
Cottage w/ On-Site Golf, Shared Pool, & Beautiful Inlet Views - Near the Beach
Save an average of 15% on thousands of hotels when you're signed in
Spectacular Oceanfront Kiawah Home With Pool And Private Boardwalk To Beach

Spectacular Oceanfront Kiawah Home With Pool And Private Boardwalk To Beach

Kiawah Island
With a stay at this vacation home in Kiawah Island (Vanderhorst Plantation), you'll be a 1-minute drive from Kiawah Island Beach and 9 minutes from Osprey Point ...
Spectacular Oceanfront Kiawah Home With Pool And Private Boardwalk To Beach
Don't see what you're looking for?
See all available properties in Kiawah Island
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.