Holiday rentals with a pool in Charleston

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

Happy Ours is a perfectly located Park Circle home featuring an open layout kitchen, dining and living room designed for gathering, lounging & entertaining. 4 bedroom home with 1 bedroom easily accessed on the first floor. The house has a private fenced lawn with outdoor dining space, grill, double porches with lovely park views, a charming porch swing & garden games available. Walk outside of your door and step into a beautiful green space perfect for hanging, exercising, games, dogs and kids.

Location · Family · Nearby

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 · EV charging

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.

Value · Family · Condition

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.

Family · Value · Laundry

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 · Checkout

Marshfront 5BD Oasis | Pool, Yard & Steps to Beach

🏝️ Private Marshfront 4BR/5BD/3.5BA Home with stunning views, saltwater pool, fenced yard, hammocks, grill & outdoor shower 📍Steps to the beach! 🛎️ Personalized concierge services by On The Coast Property Group (fees vary) • Grocery stocking • Decoration setup • Dining reservations • Private chefs • Transportation coordination • Boating/water excursions • Beach rentals • Sports equipment • Baby gear • Spa, fitness & wellness services • Event planning for celebrations/gatherings …& more!

Family · Value · River

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.

Value · Family · Condition

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 · Heating

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!

Value · Location · Grill

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..

Location · Family · View

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 · Laundry

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

Family · Location · Condition