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Holiday Rentals with Pools in Charleston

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    Travellers to Charleston are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in CharlestonView all 224 rentals
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    Relax in Designer Style!1 / 24
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Lowcountry Oasis1 / 34
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Cozy 2 Bed/2 Bath 5 miles to Beach & Downtown, Walkable to Pier & Food/Bars!!1 / 9
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Detached Guest Suite1 / 11
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2017
    I was greeted by Chuck and Jeanne shortly after arriving at their clean, comfortable & well-appointed guesthouse. Friendly & charming, they offered some suggestions on...
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    About this property
    Detached guest suite(full cable with DVR and HBO ) with full bath. Small electric fireplace for ambiance . Outdoor space, including pool , full outdoor kitchen and gas fireplace with large screen T V ( full cable with Netflix) . Separate entrance . 10 miles to downtown , 17 miles to...
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    29414, Charleston, Coastal South Carolina
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Superb One Level Home | Private POOL | Dual King Master Suites | Top Reviews!1 / 57
    (24)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    This is a beautiful, well setup home. The rooms are fabulous and extremely functional. I have hopes of staying here again. The owners were great to work with. Great place, quiet...
    Reviewed 31 July 2017
    We spent the week in Charleston preparing for our wedding. The house was just as described.....5 spacious bedrooms, 2 King / 3 Queen. Full kitchen, family room, washer / dryer...
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    About this property
    PRIVATE POOL - WATERFRONT NEIGHBORHOOD Pool Trust House All One Level. Dual King Master Suites. Luxury Bathrooms. 3 miles over bridge to Historic Charleston, 6 miles to Beach! Decking front and back plus screened porch. Fully stocked Kitchen | Outdoor Grill. Wifi - HDTV for every room -...
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    29401, Charleston, Coastal South Carolina
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Best of both worlds…Historic Charleston and beach!1 / 14
    (1)Excellent
    James Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • DVD Player
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2017
    I was impressed with the thoughtfulness of the owner. He made sure we had everything we needed . MUSC hospital was an easy drive. Stores, Folley beach, great restaurants all...
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    About this property
    This two bedroom/ two bath condo is the perfect affordable and super convenient vacation property or corporate housing. Situated exactly 5 miles from Historic Downtown Charleston and 5 miles from the beautiful Folly Beach. The condo is well-equipped with all of your necessities, from a stocked...
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    Location Information
    29412, Charleston, Coastal South Carolina
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    James Island
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only two miles from the beach, this condo is a great place to stay while in Charleston. This place has modern amenities from a jetted tub to granite counter tops. There is also a swimming pool open in the warmer months. Also enjoy a nice private balcony. There are very few places to stay close to...
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    Location Information
    29412, Charleston, Coastal South Carolina
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Housekeeping Included
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cottages on Charleston Harbor offer ten luxurious two-bedroom, three-bath Cottages with a full kitchen, living room and screened-in porch. Our guests' favorite feature at the Cottages on Charleston Harbor are the breathtaking vistas that include views of Fort Sumter, downtown Charleston and...
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    Location Information
    29464, Charleston, Coastal South Carolina
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright and airy with open Living Room, Dining Room and Kitchen - great for entertaining. Hardwood floors with terra cotta tiles in the kitchen and Corion countertops. Wrap around porch and large deck overlooking private, heated pool. (Please note: pool only heated when outside temperature is...
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    Location Information
    29451, Charleston, Coastal South Carolina
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Cute 2 Bed/2 Bath 5 miles to Beach & Downtown, Walkable to Pier & Food/Bars!1 / 15
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    We really enjoyed our stay at Jay's condo! Jay was an excellent host- very friendly and responsive. The condo was in a great location close to downtown Charleston, the beaches...
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    About this property
    Cozy, clean, private 2bed, 2 bath in safe complex w/ pool. A walkable 1/4 mile from the base of the Cooper River Bridge on the Mt Pleasant side! 4 miles to the beach and the heart of downtown Charleston, 1 mile from other shopping/food/nightlife. Pier to view the ocean and full clean playground 300...
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    Location Information
    29464, Charleston, Coastal South Carolina
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Long Vacation? Thinking of moving to Charleston? In the city, pool, marsh.1 / 49
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2015
    So you’re headed to Charleston for vacation? Terrific! Congratulations on making a great decision for visiting Conde Nast’s voted “USA’s No. 1 City for the Fourth Consecutive...
    Reviewed 24 May 2015
    Exceeded our expectations in every aspect. Beautiful setting, classic home....clean, modern, and elegant. You will not be disappointed. Tranquil location, but very convenient to...
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    About this property
    Only a few guests enjoy this private paradise, perfectly appointed comfortable home. Minimum monthly rental. Foodie kitchen and dining room with Fireplace and with marsh and tidal creek in the backyard. Best restaurants either walking or driving. Within minutes: 2 miles to the historic district, 15...
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    Location Information
    29407, Charleston, Coastal South Carolina
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located across the street from the Charleston Municipal Golf Course, a 10 minute drive to historic downtown Charleston and 15 minutes from Folly Beach Our home features a private pool with a large deck that offers outdoor dining and a championship size ping pong table
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    Location Information
    29412, Charleston, Coastal South Carolina
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is fully furnished and has five bedrooms, four baths, a large fenced yard, a pool, and washer/dryer, linens, etc. There are two very large bedrooms upstairs. One bedroom with a double bed has an en suite full bathroom and walk-in closet. The other bedroom has two single beds. There is a...
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    Location Information
    29407, Charleston, Coastal South Carolina
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Indoor Pool
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    King 583 is located in of one of America’s most charming cities—Charleston, South Carolina. Have our valet park your car, then get ready to embark on an historic vacation. Take a horse-drawn carriage ride along cobblestone streets past stately homes and graceful gardens. Shop for antiques, enjoy...
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    Location Information
    29403, Charleston, Coastal South Carolina
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    domn town charles walking distance to every where it is a new bluegreen...
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    Location Information
    29403, Charleston, Coastal South Carolina
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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