Holiday rentals with a pool in Charleston

Happy Stays, Mins to Park Circle, Dtwn, CHS Beach

Welcome to a remarkable three-story residence in Park Circle! Featuring three large, professionally designed, colorful bedrooms, each with its ensuite bathroom, it offers comfort & privacy. With five Smart TVs, a 110-inch movie screen, Pacman Arcade, Ping Pong Table, Ring Toss, Grill & other fun games, entertainment abounds. Relax on porches, take in views from the porch swing or wraparound windows, & enjoy a green space for pets & kids. A gourmet market next door serves delightful food & drinks

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!

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, have a cocktail on the balcony, or just sit and watch the sun set from the roof top deck. 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.

Little Oak Love | 5 Minutes to Folly | Marsh Views

Little Oak Love is a serene escape just a mile from Folly Beach, nestled in a gated community. This top-floor, two-bedroom, two-bath condo offers stunning views from almost every room, and ultimate privacy. 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. Plus, you're only a 20-minute drive from historic Downtown Charleston. This condo is perfect for the ultimate Lowcountry vacation experience!

The Cottage for Two

The Cottage was built in the late 1930's for a local church and was used as a Sunday school room, for receptions, etc.. In 2004 we relocated the Hut, as it was once called, to this site and restored it to it's existing condition, staying with it's late 30's roots. It and main house sets on 5 beautifully landscaped acres and is located only 7 minutes from historic downtown Summerville. Please note that this is NOT INTENDED AS A VENUE and is a SHARED POOL, not exclusive to the pool house guest.

Renovated luxury home - 10 minutes Folly/downtown

Welcome to life in the Lowcountry at The Lookout! The design of this home embodies the natural beauty of life on the water with comfort and style. Heated saltwater pool! Great place to cool off year round- close to the outdoor TV, bar/grill! Search YouTube for "The Lookout of Charleston Airbnb" to see the video tour! Conveniently located in James Island, you are 10 minutes from all the fun Downtown Charleston has to offer or 5 minutes to the beautiful pristine beaches of Folly Beach!

The Oasis (Charming, Close, Sleeps 7)

The Oasis is a beautiful and comfortable townhome in Charleston, SC. This 2 bedroom, 2.5 bath sleeps 7 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.

CHS Guest Suite w/Separate Entry 2 Bedroom& 2 Bath

**One of the few Airbnb’s with a legal permit in Charleston, SC. Just 15 minutes from downtown Charleston, SC. Free parking in my driveway! Guest suite. Own private and separate entrance. Comfortably hosts four. We charge a fee if two people want to stay in two separate rooms- the room rate is based on double occupancy. Fee is $40/ppn for 2nd bedroom Guest access to swimming pool. Complimentary coffee/coffee maker, cable TV, water bottles & juice, refrigerator.

Luxury pool, center of Folly, 2 blocks to 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!

Boho Bungalow | Private Oasis with Jacuzzi Pool

Escape to this enchanting brick cottage just moments from the harbor where historic charm meets modern comfort. Cozy up in the inviting living spaces with warm tones and exposed brick or relax in the private garden just outside. A charming bedroom awaits and you’ll adore the fully equipped kitchen perfect for intimate meals. Now featuring a brand-new dipping pool with jacuzzi-style jets and the option to heat or cool for year-round enjoyment.

Lux 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

Gated Farmhouse with Salt Water Pool

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)