Holiday 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!

Location · Value · Kitchen

4BR w/ 2 Primary Suites | Pool + Grill | Parking

Relax and unwind in Charleston! This property is perfectly situated between Charleston International Airport (9.5 miles / 18 minutes) and Downtown Charleston (16 miles / 24 minutes). Our custom-designed, modern home offers a serene retreat with beach walks, historic tours, and nature's symphony at your doorstep. Take pleasure in the wide range of outdoor amenities and bask in the lovely Charleston weather. Every moment here is an opportunity to create cherished memories with friends and family:)

Value · Family · Indoor spaces

Crushing on Charleston *Pool *Game Room *Fire Pit

You will definitely be crushing on Charleston after your stay at this charming house in North Charleston. This home has everything you need to make amazing memories with your family or group. After a day of exploring downtown, playing at the beach or visiting one of the many attractions Charleston has to offer, head back to our your own personal oasis to continue the fun at the pool, game room and fire pit. Centrally located, you can be to everything this beautiful city has to offer in minutes.

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 · Value · View

The Oasis (Charming, Close, Sleeps 5)

The Oasis is a beautiful and comfortable townhome in Charleston, SC. This 2 bedroom, 2.5 bath sleeps 5 people. The airport, beach, downtown, golf courses, & concert venues are all approx. 20 min away. After enjoying Charleston's restaurants, tours, shops, beaches, golf, & entertainment, relax at The Oasis w/ 3 Roku TVs (70", 43", 43"). Drift off to dreams w/ King, Queen, Twin Loft, & Queen Sleeper Sofa options. Also enjoy a fully equipped kitchen. There is pool access in warmer weather.

Location · Family · Indoor spaces

Red Sunsets | Luxury Furnishings | Pool & Elevator

HEATED POOL, HOT TUB, & ELEVATOR! Stay in a home not a vacation rental. Sip cocktails from the top viewing deck with beautiful red sunsets sounds, smells, and peekaboo views of the ocean, views of the Intercoastal all in the comfort of this fully appointed beach home. Short 1 block walk to the beach and marina! Bring your boat on vacation w/you and explore the waterways or just lounge and enjoy the breeze on 1 of the 3 large porches. Folly really has it all! LIC00980 ISTR, STR25-A1007

Value · Location · Comfort

Heated Pool - Marsh Front - Hot Tub - Walk toBeach

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

Value · Family · EV charging

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.

Location · Family · Back garden

The Endless Summer-Hot Tub-7 beds

Welcome to The Endless Summer! Spacious 5-Bedroom Home - Sleeping ideal for groups! Escape to tranquility in this laid-back and quiet neighborhood just one exit from the airport. The Endless Summer is ideal for both small and large groups of friends or families, offering a perfect blend of comfort and convenience. 12 min to downtown Charleston 8 min to Tanger Outlet Mall and Top Golf 6 min to Coliseum/Performing Arts 29 min to Folly Beach 8 min to the airport

Family · Location · River

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.

Value · Family · Condition

Coastal Cottage in Charming Old Mt Pleasant

Welcome to the Coastal Cottage! This spacious, family friendly house is located in the charming Old Mount Pleasant neighborhood and boasts a beautiful, spacious pool. It’s only 3 miles to Sullivan’s Island Beach, 6 miles to downtown Charleston, and less than 2 miles to Shem Creek which has many dining options, shops, and beautiful views of the water! STR Permit #ST260068 S.C. BUS. LIC. #20137920 (2025-2026)

Value · 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

Family · Value · Amenities