Holiday rentals with a pool in Dorchester County

The front entrance of the guesthouse features a welcoming porch with a green front door. Lush plants surround the entryway, and a paved walkway leads to the door. Windows on either side allow natural light to enhance the space.

4.99 out of 5 average rating, 89 reviews

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

4.8 out of 5 average rating, 145 reviews

A cozy hot tub is situated under a wooden gazebo adorned with string lights, providing a warm glow. Steps lead up to the hot tub, which is surrounded by a fenced backyard and lush grass, creating a serene space for relaxation.

Home in Charleston

Charleston Retreat, Hot Tub, Game Room, Sleeps Big

Charleston group & family retreat near airport, downtown & beaches in a quiet private community — ideal for wedding stays, reunions & vacations. Features: • Game room w/ pool table, shuffleboard & arcade • 7-person hot tub + fire-pit patio • Large kitchen & group dining space • Fast Wi-Fi + Smart TVs in bedrooms • Bikes for neighborhood exploring • Community pool, tennis court & playground • Flexible sleeping arrangements for groups • Near shopping, dining & venues • Easy self check-in

Guest favourite

A cozy outdoor patio features a round table set under a red umbrella, surrounded by stylish metal chairs. Potted plants add greenery, and a flowering plant brightens the space. The patio connects to the cottage's charming exterior, framed by lush trees.

4.81 out of 5 average rating, 37 reviews

ELEGANT COTTAGE IN HISTORIC SUMMERVILLE

This elegant cottage is nestled behind a gracious home in the historic section of Summerville directly on the path of South Carolina's Heritage Corridor. The cottage is flooded with light and color, filled with books, artwork and good vibes. Ample paved parking for vehicles of any size, commodious patios in front and back equipped with a grill and garden seating. Near Summerville's wine bars, craft beer and coffee houses. Just minutes to Middleton Plantation, Drayton Hall and Magnolia Gardens.

The image captures a serene outdoor area featuring a large swimming pool surrounded by lush greenery and palm trees. A charming cottage with a gabled roof sits near the pool, complemented by a shaded patio area. The surroundings include well-maintained landscaping and a wooden fence.

4.99 out of 5 average rating, 109 reviews

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.

A cozy seating area features a soft armchair and a tufted ottoman, positioned near a stone fireplace. Built-in shelves display decorative items and books. Expansive glass doors provide natural light and a view of the outdoor space, enhancing the inviting ambiance.

4.97 out of 5 average rating, 33 reviews

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.

The dining area features a natural wooden table set with bowls and elegant table settings. Surrounding the table are comfortable, light blue chairs. Soft lighting is provided by a modern fixture overhead. A view of the sunroom is visible through the archway, enhancing the space.

4.95 out of 5 average rating, 122 reviews

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.

4.82 out of 5 average rating, 38 reviews

A stylish living area features a green velvet sofa paired with two accent chairs and a round coffee table. A rug adds warmth to the carpeted floor. The space is illuminated by natural light from a window, while a tall plant provides a refreshing touch.

Apartment in Ladson

King Bed-Pool and Gym-Kitchen

Enjoy a stylish experience at this centrally-located place! 1BR 1BA Apartment with King Bed. Pool and 24/7 Gym access included. We are in immediate proximity of Boeing, Mercedes Benz, Cummins Turbo, Volvo and other top employers in the area. 5 mins to Charleston Southern and Trident Medical Center 5 mins to I-26 17 mins to airport 20 mins into downtown Don't see availability for your dates? Send us an inquiry. We manage other rentals in the area. Happy to help!

4.83 out of 5 average rating, 6 reviews

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.

A private saltwater pool is surrounded by a spacious patio, featuring lounge chairs and a backdrop of well-kept landscaping. The screened-in porch showcases outdoor seating and a pool table. Inside, a den offers additional recreational space, inviting relaxation and fun.

4.97 out of 5 average rating, 205 reviews

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.

4.93 out of 5 average rating, 394 reviews

The exterior of a two-story home is featured, showcasing a light green facade and a gray roof. A landscaped yard includes palm trees and large agave plants. A driveway leads to a garage, and clouds drift across a blue sky, adding to the inviting scene.

Home in North Charleston

Gorgeous Executive Home on Pond *5 beds*

Beautifully renovated 2,400 sq ft. two story home on a pond. Our home has nearly all brand new finishes including memory foam mattresses on all beds. The floor plan features a highly sought after master on the 1st floor with a very open concept floor plan. Great outdoor space with patio overlooking the pond. We’re 15 mins to Charleston airport, , I-26 and I-526, 20-30 to downtown and about 30-40 mins to beaches

A spacious living area features comfortable seating arrangements, including a swing chair and chic armchairs. A dining table accommodates multiple guests, while a dark accent wall adds visual interest. Natural light floods in through large windows, highlighting the warm wooden flooring.