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Rentals for Seniors in Kiawah Island, SC

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    Travelers to Kiawah Island are booking March dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 20
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    1 / 14
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 18
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Welcome to PARADISE! Our 3 bedroom, 2 bath free-standing cottage on Kiawah Island is a short walk to Kiawah's gorgeous beach, spacious private community swimming pool and dock (great for kayaking, fishing, sunsets...) Renovated and features new furniture, hardwood floors, Wi-Fi internet access, 50"... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed September 22, 2014
    My brother recommended Flip Key to me. It is a very friendly user service. I highly recommend this for any vacation rental. The rental was in a very good location. We were...
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    1 / 17
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Grill
    • DVD Player
    • Balcony
    • Porch
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Premier rating by the Kiawah Island Resort with Full Resort Privileges and former rental property for Ultimate Escapes, Luxury Destination Club, our cottage promises to exceed expectations for your dream beach vacation! Perfect for families or adult get-aways. Full-resort privileges allow use of... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed April 14, 2016
    Beautiful place! We loved our stay there and the kids are already asking when we can go back! The beds were so comfortable, the screened-in porch was a nice hangout spot...
    5 of 5 stars Reviewed December 31, 2015
    This was a first trip to Kiawah and it most likely won't be our last. We stayed with our adult children and all decided that we must come again. The cottage is extremely clean...
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    1 / 28
    5 of 5 stars (6) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Balcony
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    • Waterfront
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    • ?
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    • x
    About this property
    SALE! SALE! SALE! CANCELLATION EQUALS SAVINGS! SAVE $800/WEEK ON ALL OPEN FALL WEEKS, REGULAR $1,599/WEEK, NOW $799/WEEK. SAVE $200/WEEK ON ALL OPEN WINTER WEEKS, REGULAR $999/WEEK, NOW $799. Enjoy the best family, sports, beach, and romantic vacation the USA has to offer from a 4-Star villa on... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed March 23, 2015
    We spent our spring break at this beautiful villa. The pictures don't really do it justice, as the rooms are larger than they appear. The location was wonderful, a short walk to...
    5 of 5 stars Reviewed December 18, 2014
    My friends and I stayed at this condo during the Kiawah Island marathon weekend! The condo is very well maintained and clean. The view of the lagoon and golf course is beautiful...
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    1 / 39
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Balcony
    • Terrace
    • Washer
    • Waterfront
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This spectacular Villa is a first floor 2 Bedroom, 2 Bath unit on the Oceanside of this 4 story complex. Outside of the large living room deck or either of the decks off the bedrooms you can listen to the Ocean surf and take in the wonderful Sea air. Since we are first floor the protective dunes... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed August 31, 2015
    we had such a lovely stay at this property. it is beautifully furnished, fully appointed, and you can't beat the location! the owner was so friendly and kind to us as well. the...
    5 of 5 stars Reviewed September 15, 2014
    We just returned from our trip to Kiawah and found our rental exceeded all of our expectations. It was so close to the beach and a very easy walk. The sandy beach was just about...
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    1 / 26
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Second floor villa with ocean views between trees. Non-Smoking. Easy beach access, and within close proximity to tennis, golf, shopping and dining. This villa offers flexible sleeping options with 4 queen beds suitable for individuals or couples. High speed wireless internet insures you are still... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed October 23, 2014
    My sister and I stayed at this condo for several days. The view from every balcony was of the ocean. We sat out on the living room balcony every evening for cocktails. We could...
    5 of 5 stars Reviewed June 8, 2014
    Moms will love this condo....the owner has thought of everything...extra soft towels, boogie boards, plenty of dishes, silverware, pots & pans detergents, and well functioning...
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    1 / 36
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Air Conditioning
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    On the oceanfront, with nice ocean views through the treetops from the main living areas. Underwent major renovation for the 2016 rental season, which makes this a lovely, modern, oceanfront choice for your next island vacation! Easy beach access, and close proximity to tennis, golf, shopping and... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 15
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    On the oceanfront in Kiawah's West Beach Village, with ocean views! Easy beach access, and close proximity to tennis, golf, shopping and dining. Square Feet: 700 Bedding includes a King bed and a sleeper sofa. This villa can accommodate up to 4 guests. Each Shipwatch Villa includes: free parking,... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Washer
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Stylish townhouse villa with vaulted ceilings and plenty of windows that let in great natural lighting and views of the beach! Located on the 2nd and 3rd floors of the building with elevator access to the entry level. This villa offers three TV's and a DVD player, as well as hi-speed wireless... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This first floor villa has partial ocean views over the dunes from the living room, dining room and the master bedroom. Guests enjoy access to wireless internet. Square Feet: 884 The living room has deck access, opens to the dining area, and offers a big screen, flat panel TV with DVD. The kitchen... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 15
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This stunning first floor villa in an oceanfront building offers ocean views from the living room and master suit, and has hardwood floors throughout. As the name implies, you will be staying near the sound of the surf for rest and relaxation. Kiawah Island boasts 30 plus miles of paved bicycle... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed July 9, 2016
    Nicely appointed, fantastic view with this Windswept villa. Highly recommend and plan to return. Only downside is a fairly small kitchen if you like to cook and have counter space.
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    1 / 31
    4 of 5 stars (5) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • Air Conditioning
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This stunning oceanfront second floor villa features full ocean views. Great furniture in the living room and bedroom, and both tile and carpet flooring which has been added throughout the rooms. The kitchen and bathrooms have custom-made cabinets, quartz countertops and hardware. The entire villa... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed July 30, 2015
    5 Stars! This condo is amazing and we had such an enjoyable visit. Everything you hope for on a vacation was granted! The condo was clean, beautiful, well stocked with amenities...
    4 of 5 stars Reviewed December 9, 2014
    We enjoyed our stay at Windswep 4421. The kitchen had everything we needed. The balcony was slightly smaller than expected.
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    1 / 15
    3 of 5 stars (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    On the oceanfront, with dune and maritime forest wooded views. Easy beach access, and steps away from to tennis, golf, shopping and dining. Square Feet 690. Bedding includes a king bed in the bedroom suite, and a queen sleeper sofa in the living room. Each Shipwatch Villa includes free parking,... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Central Heating
    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly 3 Bedroom 2 Bath Spa Steamroom Luxury Beach Villa located in the desirably OceanWoods section of Kiawah stunning views , lush location nestled inside a maritime forrest with a 10 mile hard packed beach perfect for riding a bike , beach villa is only a stone's throw away from the... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    On the oceanfront, with views of the ocean over palm trees. This brightly decorated villa is sure to please beach-going guests with the ease of ocean access right over the beach boardwalk! Easy beach access, and within close proximity to tennis, golf, shopping and dining. Kiawah’s 30-miles of paved... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 24
    4 of 5 stars (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Air Conditioning
    • Parking
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This third floor fabulous villa has stunning ocean views from the living room, dining room and master bedroom. Kiawah Island boasts 30 plus miles of paved bicycle trails making it an easy jaunt to Night Heron Park’s green spaces and playgrounds. Bike trails also extend all the way to Freshfields... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed January 18, 2016
    The last week of 2015 was off to a rough start. At the last minute we decided to head to Kiawah. My wife had stayed at seveal of the Windswept units over the years and we were...
    5 of 5 stars Reviewed October 22, 2015
    This unit was perfect for our family. It was close to the trails and shopping and was nicely updated and clean upon arrival. We especially appreciated the updated kitchen and...
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    1 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • DVD Player
    • Washer
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This recently renovated oceanfront villa features great views from both the living room and master bedroom. Guests enjoy wireless internet access. As the name implies you will be staying near the sound of the surf for rest and relaxation. Kiawah Island boasts 30 plus miles of paved bicycle trails... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    4439 Windswept Villa is an ocean front 1 bedroom/1 bath villa just steps away from the beach for a great escape! This property is on the first floor of an oceanfront building with a private deck with steps down to the ground where you can immediately step onto the boardwalk to the beach. It offers... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
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    1 / 25
    3.5 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Relax in comfort, just steps away from the ocean waves. This townhouse-style villa, located on the fourth and fifth floors of the building, features full Atlantic Ocean views. Beautiful bamboo flooring runs throughout the villa. Kiawah Island boasts 30 plus miles of paved bicycle trails making it... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 20
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Second floor villa in the high rise building, with full ocean views has been completely renovated. Guests enjoy such amenities as flat panel TVs, high speed wireless internet, and free nationwide long distance. Square Feet 1694 The living room has a flat panel TV and window seat on which you can... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    4 of 5 stars Reviewed August 31, 2015
    Wyndham was easy & efficient to work with. The property was well maintained and nicely decorated. Lots of space in this unit, we had 4 adults and a toddler and didn't feel...
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    1 / 16
    5 of 5 stars (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Porch
    • Washer
    • DVD Player
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    4981 Turtle Point (Green Dolphin Way) on Kiawah Island . Sleeps 8 comfortably. Ideal for families with children or 4 golfers each with their own room for sleeping (so you won't hear others snore). <BR>Wireless internet access so bring your lap top computer. Very comfortable, 2 Bedroom / 2... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed 4 weeks ago
    We stayed for a long weekend with family. The condo was clean and equipped with everything we needed. As others have mentioned, it is a short walk to the beach, but the provided...
    5 of 5 stars Reviewed September 15, 2014
    This two bedroom two bathroom villa is much nicer than what is depicted in the photographs. It is well appointed, conveniently located, and an incredibly well priced villa. It is...
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    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    4439 Windswept Villa is an ocean front 1 bedroom/1 bath villa just steps away from the beach for a great escape! This property is on the first floor of an oceanfront building with a private deck with steps down to the ground where you can immediately step onto the boardwalk to the beach. It offers... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 8
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This spacious home is located on the 5th hole of the Turtle Point Golf Course, at the end of a quiet cul-de-sac. This 5200 sqft house, nestled amongst live oaks, magnolias and palms, offers spacious solitude with quiet and tranquil views, and yet is only a short bike ride/walk to the beach. Our... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 25
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • DVD Player
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    On the oceanfront, with views of the ocean through the palm trees. Easy beach access right over the beach boardwalk, and within close proximity to tennis, golf, shopping and dining. Guests also enjoy accessing the Night Heron Park and Playground, and other areas of the Island via 30-miles of paved... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 21
    2 of 5 stars (1) Poor
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Parking
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Fourth floor townhouse villa in an oceanfront building, with incredible ocean views and elevator access. Vaulted ceilings and skylights bring in lots of natural light, and allows guests to fully enjoy views of the ocean! Kiawah Island boasts 30 plus miles of paved bicycle trails making it an easy... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 17
    2.5 of 5 stars (2) Poor
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    • Satellite TV
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    On the oceanfront with views of the dunes and maritime forest wooded areas. Easy beach access from this location. Close to tennis, golf, shopping and dining in a wheelchair accessible building. The Shipwatch complex has neighborhood wireless internet service provided by the Shipwatch Homeowner's... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    3 of 5 stars Reviewed 4 weeks ago
    Overall, the property needs updating and the owner can do a few small things to make it better. Our reason for going to the beach is to go to the beach and not stay inside that...
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    1 / 28
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This oceanfront three bedroom, three bath villa offers ocean views from every room! Kiawah Island boasts 30 plus miles of paved bicycle trails making it an easy jaunt to Night Heron Park's green spaces and playgrounds. Bike trails also extend all the way to Freshfields Village. Kiawah Island's... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    1 / 6
    5 of 5 stars (14) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
    • Waterfront
    • Satellite TV
    • Balcony
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Two bedroom, two bath condo overlooking lagoon on Kiawah Island, SC. Eight minute walk from beach and pools. Five golf courses, including The Ocean Course, home of 2012 PGA. Number one rated tennis courts. Twenty minute drive from Charlestown, the number one rated hospitality city and vacation... View all property information
    Location Information
    Kiawah Island, Coastal South Carolina
    5 of 5 stars Reviewed July 26, 2016
    This condo was a great find and the owner was very helpful, providing us with plenty of information about the island and condo before arrival. The unit itself was really nice...
    5 of 5 stars Reviewed June 2, 2015
    5508 turtle cove villas was wonderful! Perfectly located and very clean & relaxing. Art was incredibly helpful answering questions and giving advice on everything from bike...
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