12 Best Vacation Rentals With Pool In Charleston - Updated 2023


Charleston is a city of rivers, estuaries, peninsulas, and small islands. Its deepwater harbor is one of the most important ports on the Eastern Seaboard. The city is home to the oldest college in the state, the first museum in the USA, and plantations that shaped the history of the American south. Charleston has several barrier islands and nature reserves that you can visit to recharge. Time your visit for the 17-day Spoleto Festival USA, an international performing arts extravaganza held every year, featuring established artists and emerging talents in more than 10 venues around the city. The annual cultural event boasts about 150 performances. The city is also proud of its top-tier accommodations for curious travelers. Here are the best vacation rentals with pool in Charleston.

1. 1950s classic home with a friendly cat (from USD 91)

This cute and charming 1950s rental is in an excellent location with one road down towards the beach and the other towards downtown. The classic interiors boast original tiling, arched doorways, and a newly renovated, fully equipped kitchen. There is a workstation with free Wi-Fi, a monitor, and a printer for those working from home.

The property is located close to Starbucks, Whole Foods, and other popular outlets. The backyard comes with a fire pit and a grill. There is also an inflated pool in the backyard that the guests need to inflate and fill with water themselves. The pump is provided. This is an ideal holiday rental for you especially if you are a cat lover. During your stay in this house, you get to feed and play with the host’s super-friendly and sweet cat named Bebe.

Central, cozy home with sweet cat - 10 min to downtown and beach!
Charleston, South Carolina, United States
23 reviews  Wifi Available
Private vacation home 4 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
this property was so perfect for our family comfortable warm and inviting
space was clean and relatively well maintained 3
the property was nice very clean comfortable and appreciated
the house was clean
the house is clean well decorated and well renovated with new appliances
clean place with everything necessary
the host was very kind and responsive
super convenient location located close to everything
perfect rental great location and cute little house
close to downtown about 10-15 minute drive away made things very easy 2
location was an easy drive to anywhere we wanted to go place was large and comfortable
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2. The Delphine (from USD 961)

A perfect blend of historic charm and contemporary amenities, this newly renovated spacious rental is located one block away from King Street in Charleston. The private European-style heated pool is the biggest attraction of this accommodation. There are 5 bedrooms and 3.5 bathrooms in total, of which the master suite has a walk-in shower and a balcony overlooking the pool and garden patio.

You also get a collection of board games, an ice machine, and free access to Spotify and high-quality speakers.

The Delphine Brand New 5 bedroom w/ Heated Private Pool
Charleston, South Carolina, United States
6 reviews Premier Host  Wifi Available
Private vacation home 12 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
awesome place new clean convenient to king st and plenty of room for a small group
location is great - just a short walk to the top of king street
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3. Restored historic home (from USD 623)

This is a charming ground-level apartment fit for travelers who prefer restored historical homes. The interiors are neat, organized, and classy. One of the best features of this short-term rental is the heated swimming pool. It’s a refreshing place to hang out after sightseeing in downtown Charleston. The shared pool is accessible to the occupants of six units within the apartment complex.

Go to the common pool deck for cocktails when you are ready to mingle. This Vrbo vacation rental with a pool in Charleston also has a dog run which is a safe area for your pets to run around freely.

Boutique Hotel Home w/ Pool 'The Dewees'
Charleston, South Carolina, United States
18 reviews Premier Host  Wifi Available
Apartment 9 Guests 3 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
the beds were very comfortable
most importantly the pool was fantastic and so nice to have on vacation with the family
every bed was comfortable & each bedroom had a bathroom
it was very clean updated and spacious
property is pretty and clean
the house was clean and appears very newly renovated with all of the modern conveniences
once i got ahold of host they were very helpful with check-in
pool was shared with other friendly guests
great location and everything needed was included
would highly recommend staying at this location
we enjoyed the location (short drive to most places) and loved the heated pool (even in december)
great coffee shop across the street (132 spring) but about a mile to the downtown & historic areas
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4. Serene cottage with beautiful garden (from USD 313)

This deluxe cottage in the Cannonborough-Elliotborough neighborhood is a well-furnished and peaceful accommodation filled with natural light from the French windows. The luxury features of this city oasis extend to the courtyard and heated pool, which is a shared area with other booked guests within the compound. The sounds from the water fountain will help ease your mind. There’s an off-street parking spot that comes with the booking.

Serene Cottage with Beautiful Garden and Heated Pool
Charleston, South Carolina, United States
400 reviews Superhost  Wifi Available
Entire villa 1 Bed 4 Guests 1 Bedroom 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
the heated pool was a glorious evening respite
the pool and patio are was remarkable
we enjoyed swimming and relaxing in the courtyard by the fountain
our stay was very comfortable and the cottage was everything per the description
the heated pool was great and was a nice feature even in february
very roomy clean apt and beautiful grounds
everything was spotless super clean i really enjoyed my time
the room was clean and beautiful
the house is beautiful very clean and modern decor style
the house was well equipped clean and comfy
courtney was very friendly and helpful
they were very responsive kind and so helpful
fallon was a gracious host who was quick to respond to all of our questions
the hosts were courteous kind and easy to get a hold of with any questions
wonderful place and very friendly hosts
the location is ideal
perfect location for our vacation
location was excellent with many great restaurants within walking distance
lovely cottage located walking distance to historic downtown
great stay very convenient location
Read more reviews

5. Contemporary riverfront guesthouse (from USD 218)

This is a self-contained apartment surrounded by oaks on the Intracoastal Waterway. You can sit down with a cold drink and watch the sunset from the apartment’s balcony. The dock is just beyond the pool and wooden deck.

The pool is accessible at any hour, so make the most of it. After a few laps, you can take an elevator in the garage and return to your pleasant quarters. When booking this listing, consider that the swimming pool is closed from November 1 to mid-April.

Riverfront Guesthouse | Heated Pool
130 reviews  Wifi Available
guest house 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
charming apartment with a great view
everything was clean and laid out nicely
we had everything we needed and the space was sparkling clean when we arrived
the owners were great during our entire stay
the owners are very friendly and were quick to respond to any questions we had
the owners are very personable and helpful
cherie and dinos were wonderful hosts that made us feel so welcomed
the property was clean and comfortable the hosts made sure that you had everything you needed
beautiful location on the river
beautiful home and wonderful central location
can’t beat the location as an easy quick drive into charleston
the location is a short and easy drive into the historical area of charleston
the place is modern clean and located near everything but in a peaceful neighborhood
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6. Gorgeous bungalow with spacious poolside (from USD 458)

This Charleston home base is a furnished bungalow with a well-maintained yard. The historic downtown is only 10 minutes away by car, while the beach is 15 minutes away. In the fenced yard, you can hang out all day in the large swimming pool and on the deck chairs. Your group will have clean towels to use courtesy of the host.

You can have a pleasant time without leaving the premises. If you are visiting with family, this is one of the kid-friendly accommodations in Charleston as well. At the far end of the pool is a shaded area with lounge seating, a ping pong table, and a foosball machine for the children to enjoy.

Charleston Bungalow
48 reviews  Wifi Available
bungalow 12 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 12
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the pool heater works well and the outside space is fun
great place to stay lots of room and sleeping space
the pool and outdoor amenities were quite nice for a large family gathering
yard and outside pool area is relaxing and well designed
the house was clean spacious and very cozy to enjoy our weekend in charleston
but it is clean and the property managers are nice
the owner has done a great job making sure everyone there is comfortable
owners were easy to contact with our few questions and the number of beds was incredible
pam the owner was fantastic to work with and was very prompt to any questions we had
the property management team is responsive and seems to want to have you have a great stay
we enjoyed the location and house
this is a lovely property - very comfortable close to downtown charleston and folly beach
plenty of parking plenty of places for people to sleep and super close to restaurants and downtown charleston
the house is clean and is in a location easy to get to downtown folly beach and grocery stores
our family of 11 and 3 pups enjoyed the location very much
Read more reviews

7. Historic downtown home with saltwater pool (from USD 907)

In this historic city, you can choose a rental that was built in the late 19th century. One of the top vacation rentals with a private pool in Charleston, this restored residence has all the original pinewood flooring and exposed cedar roofing. Its modern updates include stainless steel appliances in the kitchen, a high-end sound system, and an equipped bar in the second-floor living room.

The yard is as charming as the interiors and it boasts a saltwater pool. Guests can have the pool heated after a 48-hour notice. There is a 75 USD charge per day for more than two heatings of the pool in a week.

Downtown Charleston Historical Home with a Private Pool
Charleston, SC, US
House 8 Guests 3 Bedrooms 2 Bathrooms

8. Lakefront gem near downtown (from USD 160)

The 45-ft (14-m) infinity pool is a delightful addition to this home’s amenities. From the sunroom, you will see the three fountains on one end of the pool. Beyond the pool and landscaped yard is Lake Edmonds.

This two-story air-conditioned home features a large deck with a pergola. On the screened porch, a hand-painted table and chair set will catch your eye. Indeed, this is a top pick if you are looking for a lovely place to spend a weekend and find romantic things to do in Charleston with your significant other for 30 days or more.

Lakefront Jewel: Infinity Pool, Minutes to Downtown, Beach, Golf & Boat launch
Charleston, SC, US
6 Guests 4 Bedrooms 3 Bathrooms

9. Delightful tiny home (from USD 133)

This is a tiny house for two where you can take a breather. The climb up the loft can be challenging, but it can also be fun clambering up for the first time. There is a swimming pool in the backyard where you can bask in the sun. The tiny house occupants have exclusive use of the fenced backyard.

This listing shares the compound with a two-story home that is a rental as well. The stone path leading to the tiny house from the entrance is for your exclusive use.

Delightful new tiny home 5 minutes from downtown
23 reviews  Wifi Available
Tiny home 2 Beds 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
it was clean and would stay again
it was very clean with extra linens
it is small but very clean and good lighting
spotlessly clean and well appointed for such a tiny place
this is an adorable tiny house the highest standards of cleanliness and hosts
tyler and lauren were wonderful hosts and very responsive and accommodating
great stay at this tiny house exactly as pictured and everything you could need thanks for hosting me
cute cozy place we really enjoyed
quite and convenient driving distance to the city or great places in the area
close to lots of fun places to eat and drink
this place was just a few min drive into the city which was awesome
Read more reviews

10. Fred Street (from USD 307)

The front porch of this Charleston home is a space for intimate conversations. There is a screened porch in the back with lovely views. Meanwhile, a saltwater pool is in the backyard. You’ll be able to smell the star jasmine growing on the fence while swimming there.

You can lounge by the pool on days when you decide to forego sightseeing. At this rental, the garage has been transformed into a media room. You can loosen up there and watch television or use the Wi-Fi.

Fred Street's Pool Oasis
98 reviews  Wifi Available
Entire home 4 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
there is also a table and chairs outside for eating as well as 4 nice lounge chairs
the living room is small but cozy with a nice couch and tv
the patio and pool were perfect
it also has 2 ceiling fans for nice air flow in the sc heat
it is large and has a table and chairs for 6 plus a comfortable seating area
extremely clean and fantastic environment
sparkling clean and well maintained
clean and super cute
beds were comfortable and the house was very clean and spacious
very spacious and clean
great host and our family enjoyed the stay
seana was easy to communicate with and responsive
great place to stay friendly owner and great pool
excellent location wonderful host very comfortable home in all respects
we were very pleased with our stay and host she was very responsive great and safe location
great location between folly and chs
beautiful house and location comfortable beds
great place to stay close to everything
location is great - very private quiet neighborhood an easy 12-minute drive to downtown
loved chewing able to be close to shopping and many local attractions
Read more reviews

11. Villa close to Folly Beach (from USD 193)

This is a well-appointed villa on James Island, overlooking marshes. Guests will see the marsh from the covered porch swings. On the left side of the porch is a side yard with a swimming pool. The poolside chairs and beach umbrellas are decked in summer colors. At night, the pool area is a feast of lights.

The property is contained within a bird sanctuary. There is a tidal creek where you will find several spaces to moor a boat. Next to this rental is Dock Street Park, which is known to anglers and crabbers. Folly Beach is also minutes away from here, which makes this property one of the most comfortable vacation rentals on or near the beach in Charleston.

Villa overlooking Charleston close to Folly Beach
Charleston, South Carolina, United States
55 reviews Superhost  Wifi Available
Entire villa 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
amazing value for the outdoor living space view and pool
the wifi connection was fast and great outside on the porch and inside the villa
the living space was fully equipped and we felt very comfortable and cozy as if we were home
great hosts clean and relaxing spot in a convenient location
place was very clean with everything you could possibly need a little something for everyone
clean as a pin well stocked comfortable great hosts and a truly special setting
host is very gracious and accommodating
the owners are very friendly and helpful
the hosts were so welcoming and we loved every minute of the stay
thank you for hosting us
everything was amazing sue was a great host very accommodating highly recommend awesome stay
great location and even better host
lovely stay beautiful view and super cute house super close to downtown charleston and folly beach
Read more reviews

12. Historic downtown home with roof deck (from USD 606)

The doors of this historic downtown home are open to travelers. You can hang out on the garden-level patio, two balconies, and roof deck. Pack light, but bring lots of swimwear for your holiday in peninsular Charleston. You can wind down on the poolside every day of your stay. Indoors, there is a deluxe soaking tub in the master suite, original artwork on the walls, and remarkable antique pieces in the rooms.

2500SF Downtown 1849 home w/ pool and roof deck!
Charleston, South Carolina, United States
171 reviews Superhost  Wifi Available
Entire home 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
very comfortable with good amenities
the most beautiful air bnb great location and amazing amenities extremely spacious bedrooms and bathrooms
the pool and outdoor space is wonderful
the master bedroom / bathroom were a real treat third the outdoor space was perfect
beautifully restored historical home in an up and coming neighborhood with a gorgeous modern outdoor space and pool
clean safe and stylish
stylish and clean
such an amazing house very clean and spacious
the house was very clean and the pool was fun to use
very comfortable and clean
frank was a great host
great host quick responses and very helpful with suggestions
frank was an amazing host
frank was a great host
a responsive caring and involved host
the location is fantastic
wonderful location close to everything
great walking distance to restaurants
very close to king street easy walking distance
location was great for dining in hot spots near upper king
Read more reviews

Experience laid-back Charleston

While traveling, the places you choose to linger matter. Charleston offers new experiences and peaceful places to rest your feet. In Charleston, South Carolina, it is easy to find gracious hosts and splendid holiday homes to make the trip worthwhile.

Frequently asked questions about vacation rentals with a pool in Charleston

1. Which vacation rentals with a pool in Charleston have Wi-Fi?

Wi-Fi is a commonly provided amenity in most accommodations in Charleston. This serene cottage with a beautiful garden in the Cannonborough-Elliotborough neighborhood, this 1950s classic home with a friendly cat located near the beach, and Fred Street are among the ones to provide free and fast Wi-Fi.

2. Which vacation rentals with a pool in Charleston have parking?

The Delphine offers on-street parking at 10 USD daily. Other properties like this contemporary riverfront guesthouse on the Intracoastal Waterway or this gorgeous bungalow with a spacious poolside near downtown provide enclosed and well-lit private garages.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Deanna Kathrina is a pediatric physical therapist for children with neurodevelopmental disability, a teacher, and advocate. She is a lifelong learner who likes music for company. She’d like to see...Read more

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