Luxury Vacation Rentals in Kiawah Island

Luxury Vacation Rentals in Kiawah Island

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 170 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Kiawah Island

SM05: 5 Silver Moss property photo 1

SM05: 5 Silver Moss

5 bedrooms•4 baths
4,046 US dollars for 4 nights•
New

~$355 less than other sites

BERK37: 37 Berkshire Hall property photo 1

BERK37: 37 Berkshire Hall

4 bedrooms•4.5 baths
2,691 US dollars for 3 nights•
New

~$235 less than other sites

BHP18: 18 Blue Heron Pond Road property photo 1
Luxury

BHP18: 18 Blue Heron Pond Road

5 bedrooms•4.5 baths
4,563 US dollars for 3 nights•
New

~$405 less than other sites

FW18: 18 Flyway Drive property photo 1

FW18: 18 Flyway Drive

4 bedrooms•4 baths
2,671 US dollars for 3 nights•
New

~$235 less than other sites

SS256: 256 Surfsong property photo 1

SS256: 256 Surfsong

5 bedrooms•5 baths
2,334 US dollars for 3 nights•
New

~$205 less than other sites

OG14: 14 Ocean Green property photo 1

OG14: 14 Ocean Green

4 bedrooms•4 baths
2,303 US dollars for 3 nights•
New

~$200 less than other sites

SM11: 11 Silver Moss property photo 1

SM11: 11 Silver Moss

4 bedrooms•4 baths
2,097 US dollars for 3 nights•
New

~$165 less than other sites

PP595: 595 Piping Plover property photo 1

PP595: 595 Piping Plover

5 bedrooms•5.5 baths
3,148 US dollars for 3 nights•
New

~$240 less than other sites

Welcome to Kiawah Island

Welcome to Kiawah Island

Elevate your coastal escape with Wander on Kiawah Island. Our collection of oceanfront homes, lagoon-side villas, and marsh-view retreats pairs the polish of a five-star stay with the privacy of a residence.
These luxury vacation rentals in Kiawah Island offer chef-grade kitchens, plush linens, spa-like baths, ultra fast WiFi, and design-forward living spaces made for both focus and relaxation. Many feature private pools, outdoor lounges with fire features, and expansive decks that frame Atlantic sunrises and golden marsh light. Every stay includes pristine cleaning, smart home comforts, and 24/7 concierge support.

Destinations near Kiawah Island

Folly Beach
Charleston
Sullivan's Island
Mount Pleasant
Isle of Palms
Isle Of Palms
Hilton Head Island
Hilton Head Island
Murrells Inlet
Murrells Inlet
Garden City Beach
Garden City Beach

Available soon in Kiawah Island

BERK37: 37 Berkshire Hall property photo 1

BERK37: 37 Berkshire Hall

4 bedrooms•4.5 baths
2,691 US dollars for 3 nights•
New

~$235 less than other sites

BHP18: 18 Blue Heron Pond Road property photo 1
Luxury

BHP18: 18 Blue Heron Pond Road

5 bedrooms•4.5 baths
4,563 US dollars for 3 nights•
New

~$405 less than other sites

FW18: 18 Flyway Drive property photo 1

FW18: 18 Flyway Drive

4 bedrooms•4 baths
2,671 US dollars for 3 nights•
New

~$235 less than other sites

OG14: 14 Ocean Green property photo 1

OG14: 14 Ocean Green

4 bedrooms•4 baths
2,303 US dollars for 3 nights•
New

~$200 less than other sites

SM11: 11 Silver Moss property photo 1

SM11: 11 Silver Moss

4 bedrooms•4 baths
2,097 US dollars for 3 nights•
New

~$165 less than other sites

PP595: 595 Piping Plover property photo 1

PP595: 595 Piping Plover

5 bedrooms•5.5 baths
3,148 US dollars for 3 nights•
New

~$240 less than other sites

SM08: 8 Silver Moss property photo 1

SM08: 8 Silver Moss

4 bedrooms•4.5 baths
2,236 US dollars for 3 nights•
New

~$175 less than other sites

CP5512: 5512 Cypress Point property photo 1

CP5512: 5512 Cypress Point

4 bedrooms•4.5 baths
1,825 US dollars for 3 nights•
New

~$140 less than other sites

Featured vacation rentals in Kiawah Island

RT508: 508 Ruddy Turnstone property photo 1

RT508: 508 Ruddy Turnstone

5 bedrooms•4.5 baths
3,676 US dollars for 3 nights•
New

~$320 less than other sites

SS162: 162 Surfsong Road property photo 1

SS162: 162 Surfsong Road

5 bedrooms•4.5 baths
3,311 US dollars for 3 nights•
New

~$290 less than other sites

BH17: 17 Bufflehead property photo 1

BH17: 17 Bufflehead

7 bedrooms•6.5 baths
4,781 US dollars for 3 nights•
New

~$370 less than other sites

Oceanfront, private boardwalk and pool property photo 1
Luxury

Oceanfront, private boardwalk and pool

5 bedrooms•5.5 baths
6,609 US dollars for 4 nights•

~$585 less than other sites

River views, guest house and pool property photo 1
Luxury

River views, guest house and pool

6 bedrooms•6.5 baths
6,489 US dollars for 4 nights•

~$575 less than other sites

Stunning home close to the Ocean Course property photo 1

Stunning home close to the Ocean Course

6 bedrooms•5.5 baths
5,359 US dollars for 4 nights•

~$475 less than other sites

Stunning new property, pool and easy beach access property photo 1
Luxury

Stunning new property, pool and easy beach access

5 bedrooms•5.5 baths
10,295 US dollars for 6 nights•
New

~$910 less than other sites

Ocean, golf and lagoon views, complete luxury home property photo 1
Iconic

Ocean, golf and lagoon views, complete luxury home

7 bedrooms•8.5 baths
15,570 US dollars for 6 nights•

~$1,385 less than other sites

Highlights in Kiawah Island

Experience world-class golf courses, pristine sandy beaches, and lush maritime forests on this luxurious South Carolina barrier island.
The Ocean Course
Kiawah Beachwalker Park
Night Heron Park
Freshfields Village
Bohicket Marina

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Kiawah Island

SM05: 5 Silver Moss property photo 1

SM05: 5 Silver Moss

5 bedrooms•4 baths
4,046 US dollars for 4 nights•
New

~$355 less than other sites

BERK37: 37 Berkshire Hall property photo 1

BERK37: 37 Berkshire Hall

4 bedrooms•4.5 baths
2,691 US dollars for 3 nights•
New

~$235 less than other sites

BHP18: 18 Blue Heron Pond Road property photo 1
Luxury

BHP18: 18 Blue Heron Pond Road

5 bedrooms•4.5 baths
4,563 US dollars for 3 nights•
New

~$405 less than other sites

FW18: 18 Flyway Drive property photo 1

FW18: 18 Flyway Drive

4 bedrooms•4 baths
2,671 US dollars for 3 nights•
New

~$235 less than other sites

SS256: 256 Surfsong property photo 1

SS256: 256 Surfsong

5 bedrooms•5 baths
2,334 US dollars for 3 nights•
New

~$205 less than other sites

OG14: 14 Ocean Green property photo 1

OG14: 14 Ocean Green

4 bedrooms•4 baths
2,303 US dollars for 3 nights•
New

~$200 less than other sites

SM11: 11 Silver Moss property photo 1

SM11: 11 Silver Moss

4 bedrooms•4 baths
2,097 US dollars for 3 nights•
New

~$165 less than other sites

PP595: 595 Piping Plover property photo 1

PP595: 595 Piping Plover

5 bedrooms•5.5 baths
3,148 US dollars for 3 nights•
New

~$240 less than other sites

View all homes

Most popular amenities for vacation rentals in Kiawah Island

Private chef (13)
Outdoor pool (88)
Basketball court (106)
Ev charger (7)
Ocean view (11)
Jacuzzi (21)
Heated pool (18)
Hot tub (21)
Waterfront (41)
Beachfront (6)
Outdoor shower (31)
Ski in ski out (1)
Beach access (58)
Kayaks (2)
Bbq area (132)
Patio (107)

Other popular amenities & vacation types in Kiawah Island

Lakefront vacation rentals in Kiawah Island
Pet-friendly vacation rentals in Kiawah Island
Large group vacation rentals in Kiawah Island
Hot tub vacation rentals in Kiawah Island
Family vacation rentals in Kiawah Island
Private pool vacation rentals in Kiawah Island
Discover more of Kiawah Island

Discover more of Kiawah Island

Kiawah Island delivers untouched Lowcountry beauty at a rare scale. Ten miles of wide, soft sand meet maritime forests and shimmering tidal creeks, creating a sanctuary for dolphins, shorebirds, and unhurried days.
Golfers know the island for championship layouts like the Ocean Course, where sea breezes and sweeping views set the stage for memorable rounds. Off the fairways, glide through glassy waterways by kayak, bike shaded trails beneath ancient oaks, or catch a pastel sunset over the Kiawah River.
Quiet, refined, and effortlessly restorative, it is a destination that rewards every season. That is why Wander's luxury vacation rentals in Kiawah Island are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Kiawah Island

Why should I book a Wander in Kiawah Island over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.
Every home in Kiawah Island delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Kiawah Island?

Some of our most popular vacation rentals in Kiawah Island include SM05: 5 Silver Moss, BERK37: 37 Berkshire Hall, and BHP18: 18 Blue Heron Pond Road. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Kiawah Island?

Wander offers 170 vacation rentals in Kiawah Island, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Kiawah Island?

You can check-in to Wander vacation rentals in Kiawah Island after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Kiawah Island have WiFi access?

Yes. Every Wander home in Kiawah Island has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.