Vacation rentals with a pool in Dorchester County

Hearts & Dreams Peaceful Family Retreat w/ pool

Welcome to Hearts and Dreams Guesthouse. Our guesthouse sits on our 5 acre property behind our Main house. The property is fully fenced with electronic gate. -Large in-ground saltwater pool (not heated) shared with main house -Screened in porch, outdoor seating -Patio outdoor eating area -Gazebo -Fire pit -Play area for children with large playhouse, swingset and picnic table - Downtown Summerville 7 miles -30 miles to Charleston No parties allowed *** NO pets or any Animals allowed

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.

Pool & Hot Tub Retreat, Arcade, 85" TV, By Airport

Luxury 2,600 sq ft home with sparkling pool, relaxing hot tub, gourmet kitchen, fire pit & gas grill. 5 bedrooms (2 kings, 1 queen, 1 full over twin bunk, 1 crib), 2.5 baths. Master has workspace with dual monitors. Entertainment galore: massive 85" TV, ping pong, foosball, chess/checkers set, Pac-Man arcade, Xbox X, Switch. Stunning Arhaus & Restoration Hardware furnishings throughout. Level 2 EV charger. Minutes to golf, Topgolf, Park Circle, shopping & airport. Beaches & downtown nearby.

Cottage 1 king bed, 1 set bunk beds, heated pool

Escape to a cozy, beautifully furnished cottage nestled in historic Summerville, just a stroll away from the heart of the town. Whether you're a couple seeking a romantic getaway or a small family looking for a peaceful home base, this cottage offers the perfect blend of comfort, character, and convenience. The patio is ideal for relaxing mornings or evening meals under the stars. With easy access and free parking, it's perfect for day trips to the beach, Charleston, or a walk into town.

Luxury Farm Stay | Hot Tub, Pool & Animals

Welcome to The Days End Farm! Where modern comfort meets country charm 🌾 This home is for quiet stays only — no parties or events are allowed. A thoughtfully designed 700 sq ft farm cabin retreat tucked away on 11 acres of peaceful pastures. Located less than 45 min from downtown Summerville, 40 min from I-20, 1 hr from Downtown Charleston, and 25 min from I-95. We are a livestock property and for the safety of our animals we only allow 1 pet per reservation with a strict leash policy.

Poolside Palmetto Retreat-N. Charleston

Welcome to Poolside Palmetto Retreat! Nestled on a quiet cul-de-sac in North Charleston, this beautiful coastal inspired home offers ample room for families & friends to gather! Centrally located just minutes from the airport & everything Charleston/Summerville have to offer. Enjoy: fully equipped kitchen, sunroom with bar, game room, & in-home laundry for convenience, fenced backyard oasis complete with seasonal in-ground pool (April–October), outdoor dining area, & cozy firepit!

Share-in Dipity Refined 4 bedrooms pool not heated

Welcome to Share-in Dipity, this stylish and relaxing home has everything you need to de-stress and enjoy Charleston. This 4/2.5 home features thoughtful design touches, an incredible outdoor area with a large patio and pool, close proximity to grocery stores/shopping, all set in the walkable and quiet neighborhood of Kings Grant. Though you may be tempted to turn your trip into a staycation, we are only 25 minutes from downtown and 35 minutes to beaches like Sullivans Island.

Pool~Near Plantations~Fire Pit~Sunroom~2500 SQ FT

🌴 Charming Summerville Escape! 🏊 Private pool with childproof fence 🚨 Please put your accurate guest count when requesting to book ‼️ Peaceful home for relaxed stays - not suitable to host large events for non-guests, sorry!) 🛌 King Beds + Bunk Rooms 🎬 Big-Screen TVs 🔥 Heated & Cooled Outdoor Sunroom 🌟 Fire Pit 🏡 Fenced Yard 🚀 Fiber Wi-Fi 📍 10 min to downtown Summerville, 20 min to Charleston Airport, 30 min to downtown Charleston, 30–40 min to beaches

Rainbow Row of Oakbrook

Come be one of the first to experience the charm that Charleston has to offer and stay in this newly listed Private nook in Oakbrook, adjacent to Summerville and 18 miles to Charleston. The space has been completely renovated and is essentially brand new. This is a perfect spot for traveling healthcare professionals, business travelers, remote workers, couples in transition, or someone just looking to explore Charleston without paying Charleston prices!

Heart of Charleston

Relax with the whole family at this peaceful place to stay. This location puts you a maximum of 45 minutes to all attractions, Downtown Charleston, Beach, Plantations and public parks. Enjoy the pool and have a cook out during the season. Safe and clean neighbor hood. This space features a 400 square foot sunroom, living room and Den for lots of privacy and space. Backyard has a deck to enjoy the summer days and a pool to utilize at your leisure.

Saltwater Pool&Hot Tub-Arcade Games-Pool Table

Welcome to Pumba’s Pad – Where Hakuna Matata Meets the Best Vacation Ever! CLOSE TO CHARLESTON SC WITHOUT THE TRAFFIC! Kick back and relax at this centrally located retreat in Summerville, SC. At Pumba’s Pad, there are no worries—just good times with family and friends! Whether you're exploring charming Summerville, taking a short trip to historic Charleston, launching your kayak or hanging out by the pool, you’re in for an unforgettable stay.

Private Pool and Game Room Retreat

Escape to this stylish Summerville family retreat for 8! This renovated single-level home features a private saltwater pool, a game room with an Xbox, pool table on screened porch, and a dedicated workspace. Enjoy modern design, a fully equipped kitchen, and a large fenced yard. Perfect for a memorable getaway just a short drive from Charleston's charm, this home offers the ideal blend of relaxation and fun for families and friends.