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!

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.

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.

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.

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.

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

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.

Private Pool Oasis • Walk to Folly Beach

Luxuriate in the lagoon pool or large hot tub and listen to the ocean on this private dune. You CAN have it all: an intimate, luxurious, artsy, home on a hill above the Folly nightlife... 3 master bedrms/2 baths!) AND... ONLY 2 BLOCKS to Folly's center AND the beach.Unforgettable PORCH times! It's MASSIVE! ********One of the king beds/baths is an attached guest house. ***** Enjoy the sounds of the pool fountain and the walks to the pubs/restaurants!

Pristine Townhouse - Beach, Charleston, Pool, Fun

Stylish home with the short term guest in mind. Wood floors throughout. Views onto live oaks, park, community pool (subject to HOA opening and closing) and tennis. Sun drenched courtyard. Close to beaches, downtown Charleston, Patriots Point, Shem Creek, Alhambra Hall, Pitt Street Bridge and more. 2 queen beds and the 3rd with a twin bed & trundle. Great location. Please read house rules before booking. STR LIC ST260069; BUS LIC BL-24-005711..

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.

Luxe Beach Bungalow Ocean Views Heated Pool

Luxury furnishings and linens. Stay in a home not just an Airbnb. One block to Center Street which means you are walking distance to all the shops, bars, and restaurants on the island, the pier, and across the street from Berts corner store. Relax on the beach. Shower outside. Sip cocktails on one of the porches with beach views. Grill out by the pool. Take a stroll to dinner and enjoy some live music. LIC 063713, STR25-A0098

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)