50 Best Kiawah Island Vacation rentals on Holiday Lettings - House rentals

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1,107 Vacation rentals

29

Vacation home in Kiawah Island

Coastal South Carolina / Kiawah Island

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
This home is a picturesque 4 bedroom, 4 bath home with wonderful fairway views! It is a great home for families or groups of couples traveling together with 3 King Bedroom suites - one is an "in-law suite" with a private separate entrance and vaulted ceiling, the main m …see more

from $164 / night

$1,148 / week

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avg. 1 hour 24 minutes

from $164 / night

30

Vacation home in Kiawah Island

Coastal South Carolina / Kiawah Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
A favorite of Kiawah vacationers for years, 1040 Sparrow Pond Cottage, secluded among pines and palmettos, offers both privacy and convenience to guests. Centrally located to take advantage of all West Beach Village amenities and attractions, or if you prefer, hide away …see more

from $163 / night

$1,141 / week

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avg. 1 hour 24 minutes

from $163 / night

35

Vacation home with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This Kiawah Island vacation rental offers plenty of room for the whole family. Boasting over 4,600 square feet, 5 bedrooms, 2 living areas, lagoon and golf views, and a lengthy back deck, this home is about an 8-minute walk to the beach. The light-filled main living roo …see more

from $417 / night

$2,506 - $5,404 / week

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from $417 / night

25

Vacation home with swimming pool, golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This Kiawah Island vacation rental features four bedrooms, a private pool, and is about a 5-minute walk to the beach. Situated on a quiet cul-de-sac, this renovated home offers golf views and is adjacent to a lagoon with bridge for viewing wildlife and flora. The main l …see more

from $415 / night

$2,506 - $4,102 / week

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from $415 / night

24

Vacation home in Kiawah Island

Coastal South Carolina / Kiawah Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
This friendly, gold rated three bedroom Vanderhorst plantation home is on a peaceful lagoon. It has an open, congenial floor plan with lots of windows. RATES VARY BY SEASON. SEE SEASONAL WEEKLY RATES BELOW FOR ACCURATE WEEKLY AND DAILY PRICING . WEEKLY OR LONGER STA …see more

from $163 / night

$1,137 - $2,372 / week

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avg. 2 hours 30 minutes

from $163 / night

32

Home rental in Kiawah Island with swimming pool, golf nearby

Coastal South Carolina / Kiawah Island

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This stunning luxury Kiawah Island oceanfront vacation rental offers three levels of indoor and outdoor living space, seven bedrooms with private bathrooms, a heated pool and spa, and its own boardwalk to the beach. The home was fully renovated for Summer 2016. The home …see more

from $1,250 / night

$7,504 - $24,906 / week

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from $1,250 / night

26

Vacation home with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
Our 4-bedroom house is spacious and filled with light. Decor is comfortable, casual and cheerful. We are one-third of a mile from the fabulous Kiawah Island Beach. You can walk this in 9 minutes or less and bike it in 3. Our street is very quiet, and leads straight …see more

from $275 / night

$1,925 / week

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from $275 / night

(6) Excellent 

29

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Relax and enjoy this beautiful 5,000 sqft house on the Kiawah River. The private dock on deep water access with floating dock awaits your daily and evening cruises on your boat. Enjoy fishing, crabbing and skiing up and down the river. The pool is surrounded with d …see more

from $550 / night

$3,800 - $9,135 / week

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avg. 3 hours 21 minutes

from $550 / night

(5) Excellent 

60

Vacation home with shared pool, golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
Relax while enjoying the sunset over the picturesque Kiawah River from the deck of our Inlet Cove Cottage. Ten miles of pristine beach are just 400 yards away. The difference is in the details; recent total renovation, beautiful décor, interesting art, great outdoor a …see more

from $250 / night

$1,025 - $2,850 / week

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from $250 / night

23

Vacation home with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
We built this house just over 10 years ago and added the heated infinity edge pool in 2010. It is a perfect house for one or two families to enjoy all that Kiawah Island has to offer - its world class golf, tennis & beach or its proximity to beautiful and historic Charl …see more

from $996 / night

$6,975 / week

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from $996 / night

24

Vacation villa with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This beautifully renovated Kiawah Island vacation rental is only 25 miles from the historic city of Charleston on Kiawah Island’s West Beach. Being located on the first floor with tennis views and only a short walk to the beach and Cougar Point golf course make this the …see more

from $134 / night

$700 - $1,365 / week

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from $134 / night

(1) Excellent 

22

Vacation villa with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Stay in exquisite comfort in our newly acquired, totally refurbished Turtle Cove villa as you enjoy Kiawah's world-renowned golf courses and 10+ miles of pristine lowcountry beaches. Our location offers the ideal launching point for island explorations and is just a sho …see more

from $225 / night

$1,575 / week

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avg. 1 hour 21 minutes

from $225 / night

24

Vacation apartment with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This 3rd floor 2 bedroom Kiawah Island oceanfront vacation rental showcases elevated ceilings and beautiful Kiawah Island ocean views. The villa features a calming color palette, soaring ceilings and abundant natural light in the main living space, hardwood flooring thr …see more

from $207 / night

$1,106 - $2,702 / week

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from $207 / night

24

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This Kiawah Island vacation rental is in Vanderhorst Plantation and has custom touches including natural hardwood floors, granite countertops, upscale molding, custom cabinets, GE Profile refrigerator, Bosch dishwasher, Wolf range and a wine cooler. The home backs up to …see more

from $250 / night

$1,505 - $5,502 / week

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from $250 / night

30

Vacation home with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
The house has wonderful architecture, with many seating places and areas to gather or be private. The house is sited on a big lagoon with thrilling 'gator and bird views. A lovely screen porch and deck add to the enjoyment. It is a 7 minute, shaded, paved walk to re …see more

from $625 / night

$3,700 / week

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from $625 / night

24

Vacation cottage accommodation

Coastal South Carolina / Kiawah Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This Kiawah Island vacation rental offers three bedrooms, community pool access, and about a 3-minute walk to the beach. The cottage features an open floor plan with three bedrooms, screened porch, and wraparound deck. The living room offers comfortable seating, TV, and …see more

from $182 / night

$1,001 - $2,100 / week

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from $182 / night

24

Vacation home in Kiawah Island

Coastal South Carolina / Kiawah Island

6 15 Min stay varies

  • 6 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This Kiawah Island vacation rental offers six bedrooms, a private pool, and is about a 5-minute bike ride to the beach. Situated on a quiet cul-de-sac with lagoon views in the Vanderhorst Plantation, this beautiful and spacious home is adjacent to the bike path for easy …see more

from $525 / night

$3,206 - $10,500 / week

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from $525 / night

24

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
The paradise of Kiawah Island is calling your name - and this villa is the answer! You'll enjoy private wooded views from the screened porch, access to shared tennis courts, and a great location just a short walk from the beach! Located in East Beach Village, this condo …see more

from $117 / night

$819 / week

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avg. 1 hour 24 minutes

from $117 / night

18

Vacation home with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Welcome to Whimbrel... The moment you open the front door and step into the foyer, your eye will be drawn to the expansive views of Kiawah Island's Osprey Point's 8th green and the new salt-water swimming pool. (NOT a dipping pool) Located behind the second security g …see more

from $505 / night

$3,000 - $7,400 / week

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Responds fast!
avg. 1 hour 8 minutes

from $505 / night

28

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
This Kiawah Island oceanfront vacation rental has 6 bedrooms, a private pool, a gorgeous panoramic view of the Atlantic Ocean, Ibis Pond, and the legendary Ocean Course Golf Course, and is only a short bike ride from the beach. The open floor plan on the main floor feat …see more

from $650 / night

$3,906 - $11,501 / week

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from $650 / night

(6) Excellent 

28

Vacation villa in Kiawah Island

Coastal South Carolina / Kiawah Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
SPECIAL ANNOUNCEMENT! We are excited to announce that the Holloway Kiawah Island Turtle Point Villa has been TOTALLY RENOVATED with construction completed January 6, 2018. All our renters in 2018 will enjoy brand new 5-Star Rated Villa luxury accommodations AT OUR 2017 …see more

from $269 / night

$999 - $2,799 / week

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from $269 / night

26

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Near the corner of Flyway and Bufflehead in the exclusive Vanderhorst Plantation, this home is an elegantly renovated, professionally decorated, spacious 5 bedroom, 5.5 bathroom Kiawah Island vacation rental offers plenty of room to sit back and relax with family and fr …see more

from $484 / night

$2,905 - $11,900 / week

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from $484 / night

(4) Excellent 

18

Vacation villa rental

Coastal South Carolina / Kiawah Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
The Cottage is conveniently located for families looking to be close to the Kiawah Island activities and the beach. These individual home cottages are located in a quiet, beautiful area surrounded by moss covered live oaks and palmetto trees. You will find an easy walk …see more

from $175 / night

$1,260 - $5,200 / week

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avg. 2 hours 26 minutes

from $175 / night

20

Vacation villa in Kiawah Island

Coastal South Carolina / Kiawah Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Exceptional Villa located in East Beach on Night Heron Lake. Excellent view of Night Heron Lake from the master bedroom, kitchen, living room, and deck. Sanctuary and East Beach Center are both in walking distance. You will be one hundred yards from Night Heron Park and …see more

from $150 / night

$1,085 - $4,500 / week

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avg. 2 hours 26 minutes

from $150 / night

24

Vacation home with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This Kiawah Island vacation rental is located behind the second gate in the exclusive Vanderhorst Plantation. The home offers the privacy that is tough to achieve when renting a shared villa building, yet is a short 7-minute bike ride to the beach. Built in the mid-1980 …see more

from $167 / night

$1,001 - $2,450 / week

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from $167 / night

26

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
4849 Turtle Cove Villa is a two-bedroom, two-bath villa bordering peaceful lagoons and has a landscaped wooded setting in East Beach. It has a convenient location close to Turtle Point Golf Course and Clubhouse, the beach, and tennis. This is a first-floor unit with a …see more

from $110 / night

$770 / week

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avg. 1 hour 24 minutes

from $110 / night

17

Vacation villa in Kiawah Island

Coastal South Carolina / Kiawah Island

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
1st Floor 1 BR 1.5 BA Windswept Villa for two (beds for up to 4 adults) on the ocean side of the street. Amenities: Large living room with 50 in. widescreen smart TV, DVD and XFinity highspeed WIFI and cable TV. Bedroom with king bed with memory foam mattress, armoire, …see more

from $145 / night

$980 - $1,250 / week

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from $145 / night

16

Vacation home in Kiawah Island

Coastal South Carolina / Kiawah Island

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Our home is situated at the end of a cul de sac on a quiet street, so your children can ride their bikes in the street in front of the house. It has a large screened porch overlooking the pool and a front porch with rocking chairs. The well-equipped and updated kitche …see more

from $275 / night

$1,600 / week

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avg. 2 hours 24 minutes

from $275 / night

24

Vacation villa rental

Coastal South Carolina / Kiawah Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This second floor Kiawah Island vacation rental has been completely renovated, features a screened porch overlooking a peaceful lagoon, and is a 5 minute walk to the beach. The living room boasts a wall of sliding glass doors that open directly to the screened porch. Co …see more

from $152 / night

$805 - $2,100 / week

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from $152 / night

(1) Excellent 

24

Vacation home with swimming pool, golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This lovely Kiawah Island vacation rental home located at 258 Governors Drive, offers 3 bedrooms and bathrooms, a private heated pool, and views of Osprey Point Golf Course. Conveniently located on Governors Drive, the main thoroughfare in Vanderhorst Plantation, the ho …see more

from $250 / night

$1,505 - $4,501 / week

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from $250 / night

4

Vacation home in Kiawah Island

Coastal South Carolina / Kiawah Island

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Pets Welcome. Gated Community Swimming pool in the community and short walk to beach. 4 Bicycles come with the property. 3 bedrooms, 2 baths with porch and fully equipped kitchen. Perfect for a family and friends. Come enjoy beautiful Kiawah Island for a short stay or a …see more

from $250 / night

$2,100 / week

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from $250 / night

26

Vacation home with shared pool, golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This renovated 3 bedroom, 3 1/2 bath home looks onto the 13th hole of the Jack Nicklaus designed Turtle Point Golf Course. This Kiawah Island vacation rental offers a wide open floor plan with a remodeled, fully-equipped kitchen flowing into the dining area and living r …see more

from $200 / night

$1,204 - $3,500 / week

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from $200 / night

25

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This Kiawah Island vacation rental has a large wrap around porch and white picket fence. It is only a 3 minute walk to the beach, steps away from the community pool, offers Turtle Point golf course views from the front and beautiful lagoon views from the back. The home …see more

from $250 / night

$1,505 - $5,901 / week

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from $250 / night

24

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This home offers stunning golf and lagoon views, 4 bedrooms, generous outdoor space, and traditional charm. Situated on Osprey Point Golf Course, the home is a 5 minute bike ride to the beach. The main floor back deck offers plenty of space, whether you prefer to dine u …see more

from $200 / night

$1,204 - $3,101 / week

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from $200 / night

24

Vacation villa with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This first floor end unit Kiawah Island vacation rental is completely updated with beautiful furnishings and amenities. Your surroundings, decorated in the colors of grass, sea, sand and sunshine, will help you unwind and relax during your time on Kiawah Island. Th …see more

from $134 / night

$700 - $1,365 / week

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from $134 / night

24

Vacation villa with golf nearby in Kiawah Island

Coastal South Carolina / Kiawah Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
This Kiawah Island vacation rental offers 3 bedrooms and bathrooms, private deck, and is a 3 minute walk to the beach. The villa underwent extensive renovations in Spring 2016, including opening up the kitchen, raising the second floor ceiling, renovating all the bathro …see more

from $172 / night

$1,001 - $2,506 / week

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from $172 / night

26

Kiawah Island Vacation home rental

Coastal South Carolina / Kiawah Island

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This Kiawah Island vacation rental home is just steps from 2 beach accesses! Getting your toes to the sand is so easy, especially because one of the boardwalks has a ramp. Located in a quiet, private cul-de-sac just off Flyway Drive, this well-decorated home features 5 …see more

from $417 / night

$2,506 - $9,905 / week

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from $417 / night

26

Vacation home rental

Coastal South Carolina / Kiawah Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
When you enter this 4 bedroom Kiawah Island vacation rental, located at 307 Palm Warbler Road, you are greeted with natural light, wide planked hearts of pine floors, wonderful lagoon views and a warm feel. The relaxing lagoon and golf views can be enjoyed from sunrise …see more

from $317 / night

$1,904 - $4,501 / week

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from $317 / night

31

Vacation home in Kiawah Island

Coastal South Carolina / Kiawah Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
This spacious 3 bedroom villa overlooks the ocean and is just steps away to the beach! Located on the 2nd floor, this unit is accessible by stairs and elevator with sunlight coming in from every corner. The deck off of the living room is the perfect place to enjoy the …see more

from $163 / night

$1,141 / week

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Responds fast!
avg. 1 hour 24 minutes

from $163 / night

51

Vacation home rental

Coastal South Carolina / Kiawah Island

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
This beautiful home tucked away in the exclusive Vanderhorst Plantation on Kiawah Island is just a few minutes walk to the beach overlooking the Turtle Point Golf Course. The beach is just around the corner! This home was just updated in 2018 and features new bathrooms …see more

from $183 / night

$1,281 / week

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Responds fast!
avg. 1 hour 24 minutes

from $183 / night