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!

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.

Oceanfront Sea Cabin 226 B - Discover Charleston!

Positioned right in the heart of 🌴 Isle of Palms 🌴 this charming 2nd floor condo is just steps from a private pier and sandy shore, with shopping, dining and entertainment close by. Enjoy a panoramic view of the Atlantic Ocean from a private balcony overlooking a community pool and beautiful natural dunes. Unwind and relax with breathtaking sunrises that paint the sky. 👉 Located just off the IOP Connector, making a trip to nearby Mount Pleasant or Downtown Charleston is easy and stress free!

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.

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.

Key Lime Condo

Located in the Front Beach district of Isle of Palms, about one block from the beach and right in the middle of all the fun. Walk to all Front Beach restaurants and bars including Papi's Taqueria, Coda del Pesce, and the world-famous Windjammer. Guests can enjoy the condo pool and plenty of free on-site parking. There are 16 units in this converted beach hotel. All are individually owned. Pandemic Info: The unit has its own HVAC system so you won't be sharing "air" with anyone. :)

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