Family-friendly holiday rentals in Charleston Harbor

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!

Lovely Garden Suite for One Guest. Bathrm/Parking

STR Lic# STR260038- Bus.BL-24-000300 Beautiful Garden Suite Room , private 3 piece bathroom and private entrance and garden. just can't be beat. Located in Old Village. 5 minutes to Beach, 10 to downtown Though there is a Queen Bed this is for ONE GUEST ONLY. NO EXCEPTIONS. The room is very comfortable with Fridge, Coffee Maker and Microwave. There is a work desk and chair with a beautiful view of the garden. Located in Old Village. No TV, strong Wifi. Bicycle provided, safe neighborhood.

★Delightful guest house near historic plantations★

Nestled in the Historic Plantation District between Summerville & Charleston, our timberframe "bunkhouse" offers privacy, comfort & convenience. This 850+ sq ft retreat includes full kitchen & bath, 2 dbl beds, twin bed & plenty of living space. There's a private entrance, so come & go as you please (we're right next door if you need us). Minutes from Middleton Place, Drayton Hall & Magnolia Gardens, an easy drive to dntn Charleston, historic S'ville, beaches & golf courses. *Now with WiFi*

Charming Old Village Retreat Fenced Yard ShemCreek

Experience The Old Village Retreat, a cozy ranch house in historic Old Village, Mount Pleasant. This charming 3-bedroom, 1.5-bath home comfortably fits a group, offering a modern kitchen, fenced yard, fire pit, and screened porch with outdoor dining. Steps from Shem Creek and minutes to beaches, it's perfect for a pet-friendly Lowcountry escape. Enjoy tranquil live oaks and easy access to dining, shops, and coastal adventures. Mount Pleasant STR Permit #ST260154 Business License: BL-24-003896

The Darby House / Beach / Shem Creek / Old Village

Welcome to The Darby House! The Darby House is a luxurious 4 bedroom home located in a family-friendly neighborhood backing up to Charleston's Shem Creek Waterway. Only a short walk to the Old Village District, local shops, restaurants, bars, or a bike ride to Sullivan's Island Beach! Newly built 4BR/3.5BA house with new TVs in each room. Amazing entertainment space with a fenced-in front yard, outdoor patio, corn hole, and grill area. MP STR Permit: ST260104; Business License: BL-24-011322

The James: “Tiny” Home b/w Downtown & Folly

The James is a unique 530 sq ft retro coastal tiny home located in a gorgeous neighborhood on James Island ◡̈ 10 mins to downtown Charleston 12 minutes to Folly Beach Walking distance to restaurants The James sleeps up to 6 people and 2 dogs (NO PET FEE) & boasts a private fenced yard & patio with an outdoor shower and Clawfoot tub! The James is ideal for solo travelers, couples, families, those traveling w/ their dog(s), those w/ limited mobility and groups of friends. #BNB-2023-02

Old Village 2bd Home, Near Sullivans + Downtown!

Tucked beneath the oaks in Mount Pleasant's beloved Old Village, this inviting retreat is the perfect place to slow down and experience the Lowcountry at its best. Thoughtfully designed with bright, welcoming spaces and plenty of room to unwind, it's ideal for couples, families, or friends. Spend your days exploring waterfront parks, hopping on the ferry to downtown Charleston, dining at neighborhood favorites, or relaxing at nearby beaches before returning to your own peaceful escape.

Make Yourself at Home

Brick ranch, conveniently located between Downtown Charleston and Folly Beach, 5 minutes to King Street, 20 minutes to Mt. Pleasant and 30 minutes to airport. Full house with 3 bedrooms, 2 bathrooms, open kitchen, dining room and large living room with big screen tv. A screened porch, fenced in backyard, washer & dryer , on site parking for 4 vehicles. Walking distance to 2 playgrounds, tennis court, wildlife sanctuary, state park and a great view of Fort Sumpter and the city.

*Old Village/Shem Creek Charmer*NEW 2BR Guesthouse

LOCATION, LOCATION, LOCATION! Welcome to Persimmon Place, a new guesthouse in the heart of Old Village in Mt. Pleasant. Historic Old Village is one of Charleston's most beautiful neighborhoods, central to all Charleston has to offer. This 2BR 1 BA is the perfect spot for your Lowcountry visit. -Walk to Shem Creek with bars, restaurants, & water activities -Less than 4 miles(8 min drive)to Sullivan's Island Beach -5 miles(9 min drive)to downtown Charleston ST260213 BL20137971

Luxurious Artist's Home

Located within minutes to world-class restaurants, beaches and historic downtown, this home features the perfect combination of elegance, art and southern charm. Whether escaping for a getaway, seeking leisure, or looking for a fun-filled vacation, this home is perfect. Enjoy a private sauna, a 72" clawfoot tub, plush towels, luxurious beds, a well-appointed kitchen, surround sound, HD TV, streaming services, outdoor living and original art. ST permit ST260123 BL-24-005864

Upscale EARL CRT 3-bdrm Old Village/Shem Creek

STR PERMIT #ST250176 BUSINESS LICENSE #20135982 3-bdrm Earl's Court neoclassical upscale home, nestled in the heart of the historic Old Village, offering the charm of low country living. Just a block from Shem Creek bars & restaurants, Old Village shops & eateries, Alhambra Hall, Pitt St Bridge, and a weekly all food Farmer's market, featuring low countries finest! The Arthur Ravenel Bridge, downtown Charleston, Sullivan's Island & IOP beaches are all bike riding distance.

Coziest Townhome in the heart of Mt. Pleasant

Pleasant Places is conveniently located to the beaches, Shem Creek’s popular restaurants and tourist attractions and is minutes from Historical downtown Charleston. Drive, walk or bike to many local attractions and restaurants. 20 min from Charleston Airport 10 min from Sullivan's Island and Isle of Palms 8 min to Downtown Charleston 5 min to Shem Creek Bars & Restaurants 5 min to grocery stores - Whole Foods and Trader Joes ST260067 MP BL-24-016987