Vacation rentals with a pool in Charleston

Pleasant Place New Build + Pool Great for Families

Bring your family & enjoy our brand new 2020 built home minutes to downtown Charleston, only 6 miles from the beach! Pleasant Place is in the BEST location to top restaurants & activities. This lovely 2700sqft 4 BR 3 BA pleasantly sleeps 10 guests and has all the familiar comforts of home with a fenced-in pool oasis, on a quiet street within walking distance to the Ravenel bridge connecting you to the heart of Charleston. Just a few minutes drive to the best beaches. Bring the family, book now!

Value · Location · Cleanliness

Salt of the Island Retreat w/ Pool on the Lake

Welcome to Salt of the Island Retreat! Tucked away on James Island and very conveniently located between Historic Downtown Charleston (10 minutes away) and Folly Beach (15 minutes away), this hidden gem is nestled on a 5 acre lake, immersed in a vibrant ecosystem! After visiting all of the eclectic charm that Charleston has to offer, head back to Salt of the Island Retreat and reconnect with nature. Enjoy the sunshine and a cold beverage poolside while you heal your soul with the simple things.

Location · Value · View

Villa overlooking Charleston close to Folly Beach

Nestled in a bird sanctuary on an oak filled tidal creek lot with expansive porch views of Charleston harbor, come share a coffee with friends and family and watch a spectacular marsh morning sun rise. Located minutes to the famous "Edge of America" Folly Beach, beach chairs, coolers and towels are provided for an enjoyable beach excursion. Centrally located, you are a short trip to historical Charleston, James Island County Park Splash Zone, and neighboring barrier islands. Off street parking.

Family · Location · Outdoor spaces

Little Oak Love | 5 Minutes to Folly | Marsh View

Little Oak Love is a serene escape just a mile from Folly Beach, nestled in a gated community. This top-floor (must be able to climb 2 flights of stairs to access condo), two-bedroom, two-bath condo offers stunning views from almost every room. Sip your morning coffee or catch sunset views from the screened lanai or balcony. Enjoy access to the community pool, pavilion, gas grill & fire pit. Only a 20-minute drive from historic Downtown Charleston. The ultimate Lowcountry vacation experience!

Location · Family · Outdoor spaces

Mount Pleasant oasis near beach with private pool!

Beautifully updated Mount Pleasant home with a pool! The home's perfectly located just a few short miles from the IOP beaches and a stone's throw from great shopping nearby. This house is the perfect spot for a family vacation or just a weekend away with friends as it offers 3 bedrooms (2 with queen beds and 1 with a king bed). You can enjoy a day at the beach (5 mins away), just relax by the pool, or swim laps in the endless pool system with a push of a button. LIC# ST260331 Bus# 20139685

Family · Location · Getting around

My Happy Place

This is a charming cottage with a pool and large outdoor area. It is located 3 minutes to both I26 and 526, a 10 minute drive to downtown Charleston and walking distance to North Charleston’s trendy, fun area. The Credit One Stadium on Daniel Island is a 10 minute drive, the Isle of Palms and Sullivans Island 15 minutes and North Charleston Colliseum 5 minutes. It is easy to get to all these places and there are many fun things to do in the Charleston/North Charleston/Daniel Island areas.

Location · Family · Pool

Beautiful 2BD/2BA Seabrook Island Villa

Enjoy beach living in this beautiful two bedroom, two bath villa! Just 23 miles from downtown Charleston, Seabrook is a gated, 2200 acre resort community with multiple luxury amenities. This end unit villa overlooks the 15th fairway on Crooked Oaks golf course, and is just steps away from a private pool available only to residents and guests of Live Oak Villas. Beach and pool access, Seabrook Island Beach Club, and dining with spectacular views of the ocean, are located only a mile away.

Family · Location · Walkability

Heated Pool-Walk to Beach-Hot Tub-Walk to Beach!

Come enjoy the most stunning views on Folly! With four private patios, a Private heated Plunge pool, a hot tub, and plenty of area's to relax - all overlooking the quiet, serene marsh; you are able to see amazing wildlife all around you while in complex relaxation mode. With two king beds, two queen beds, a bunkbed and 3 full bathrooms - there should be plenty of room. Enjoy tons of games, Golf hitting bay, darts, ping pong , swings and kids play area! STR23-0364799CF LIC00726

Family · Location · River

Gorgeous home one block from beach w/ heated pool

Have fun with the whole family at this stylish place. This home is ideally located walking distance to the beach and near everything IOP has to offer. Enjoy sunsets on the rooftop patio and spend hours swimming in the pool. The home is ideal for families with a number of games, shuffle board, bikes, a golf cart, four patios, and tons of interior space. The home has all new furniture and is stocked with everything you need to enjoy your stay and feel like you are at home.

Family · Location · Amenities

2500SF Downtown 1849 home w/ pool!

The perfect Oasis in the middle of the Peninsula... Come home to this 2,500 SF c.1849 historic property and take a dip in the pool after a long day walking around or relax and have a cocktail on the balcony. Walk out the door and explore Cannonborough-Elliotborough and some of the best restaurants the City has to offer. Off-street parking for 1-2 vehicles is provided, a rarity downtown. We are a legal City licensed short-term rental 2026 OP. 07096.

Family · Value · Wifi

Gated Farmhouse Loft with Pool & Hot Tub

Gorgeous guest retreat above detached garage with pool access. Seven miles from Historic Downtown Charleston. Minutes from restaurants and the beach. This cottage is the best place to celebrate a special occasion! Send simple decorations through Amazon and we will decorate for you! Beach chairs, umbrella, and towels provided for your day at the beach. Business License Number (LIC063755)

Family · Location · Air conditioning

Private Pool | Only 1 Block to King | Sundance

Welcome to Sundance, a spacious and inviting Charleston home located in the heart of downtown! This classic single-family retreat is perfect for families or groups of friends, offering comfortable gathering spaces and a private pool for relaxing after a day of exploring the city. An ideal home base for enjoying everything Charleston has to offer. Permit Number: 06857

Location · Value · Indoor spaces