Family-friendly holiday rentals in Charleston

The Backpacker

Our "Backpacker" is a cute and cozy 96 sq.ft. of tiny house nirvana. Situated on a small tidal slough, it provides a beautiful natural setting for reflection and appreciation of that which is good in life. For those looking for luxury, the Backpacker is not for you (you may encounter bugs and it's really hot in summer). However, the Backpacker has a pretty cool vibe, and is extremely convenient to historic Charleston and Funky Folly Beach. The Backpacker is for backpackers and nature lovers.

Historic Vintage Charm | Private Modern Luxe

Turn back time in this refined historic Charleston residence (OP2025-06356). Soaring 12-ft ceilings, polished wood floors, and grand sash windows set the tone for an elegant retreat. A master bedroom and curtained sunroom each offer king beds for flexible sleeping. Located in a quiet, walkable historic downtown neighborhood. Perfect for couples or a sophisticated girls’ weekend. Private entrance, thoughtfully designed 1,000 sq. ft. interior. Exclusive off-street parking with EV charger.

James Island Creek Retreat | On the Water |

Welcome to my low country home on James Island, located on a tidal creek within a quiet family neighborhood. The large backyard is on a beautiful marsh with water access allowing for amazing views. It’s 7min from downtown and 10min from Folly Beach. Perfect central location on James Island to everything Charleston has to offer. As a certified US Coast Guard boat Captain I offer discounted private tours to guest. Please book ahead as the summer gets busy. IG Huckleberry_Boat_Tours for photos

Farm Stay w Gardens, Cute Animals, Firepit + Porch

Welcome to the farm! This cute little farm studio is ready for your enjoyment! With a horse front view and rows of flowers in sight, you will be sure to soak in all the feels of farm life all while being close to West Ashley, 30 minutes from Down Town Charlestion and 35 min from beach access. Tucked in behind the hustle and bustle of city life you can put your feet up and relax, walk the gardens or check out the cute farm animals. Truly this is a unique stay that you don't want to miss!

Perfect Tiny Cottage, Historic Downtown Charleston

So much to see, do, and eat near this cozy spot! Nestled in a quaint neighborhood of historic downtown Charleston homes (families & college students), this lovely studio tiny house is situated just 3 blocks from central King St. Only a 10 minute walk to Charleston's best shops and restaurants including Chez Nous and Callie's Hot Little Biscuit, as well as College of Charleston and MUSC. A quick ride to historical attractions, breweries, and the beaches of Sullivan's Island, Folly, and more.

Heart of Park Circle| Peaceful & Private | Firepit

Enjoy a stylish and peaceful stay at this centrally-located, Park Circle cottage. Set back from the street for added privacy, with a beautiful front porch and backyard. Just a 5 min walk to the lively restaurants of Park Circle and a short 20 min drive to Historic Downtown Charleston & nearby beaches. Filled with an abundance of natural light, featuring two bedrooms, one bath & a sunroom with a daybed. Fully equipped with all you need for a comfortable stay in the Park Circle neighborhood!

Kate's Place: The romantic retreat on the coast

Welcome to Kate's Place, a cozy and very clean vacation getaway in Mt. Pleasant. Many guests have described Kate's Place as an ideal retreat, given its close proximity to beaches (one mile away) and restaurants. Downtown Charleston, a ten-minute drive. This apartment has an exterior door with no shared indoor space. A private parking spot to boot! You'll love Kate's Place! Perfect for two! Do check out all the 5-STAR reviews! TOMP Permit Number - ST260355 TOMP BL# - 20132913

Cannon St. Suite D

Location Location Location this upstairs one bedroom apartment renovated to the studs in 2015 right in the heart of down town Charleston. Located at Cannon apartment D is walking distance to some of Charleston's best shopping, renown restaurants, bars, historic district and MUSC. This apartment boasts beautiful new hardwood floors, new cabinets, stainless steel appliances, stackable washer-dryer, new furniture outfitting the entire apartment, front balcony and two onsite parking spots.

Bright, clean and close to everything!

You and yours will enjoy easy access to everything Charleston has to offer from this centrally located 1 bedroom apartment. -10 minutes to Downtown Charleston -15 minutes to Folly Beach -2 minutes to the public golf course, yes you read that right! Close to everything, check! Our 1 bedroom apartment offers a California king bed, a spacious kitchen, off street car+boat parking, personal washer & dryer and of course, WiFi. Need more? Just ask! We are happy to accommodate.

Silverlight Cottage in Park Circle

A spacious retreat (780 sq ft.) in Park Circle: Elegant, gracious + charming. Brand new custom built guest house designed with a nod to classic Charleston architectural influence: open concept indoor - outdoor space to large shady screened porch where a perpetual breeze from the not-too-distant coastline blows gently all year round. Visitors will return from their travel deeply restored and revived - having experienced well-appointed accommodation.

Quaint Cottage Studio in Ashley Forest (Avondale)

This property is a midterm rental intended for traveling nurses, medical professionals, academics, etc. We are a small family with a dog and two young kids. The studio is in a safe, charming, and quiet location 10 minutes from downtown, MUSC, and CofC. You will have access to our outdoor living space and dining area, as well as a parking spot in our driveway. The studio is fully furnished with a small refrigerator, microwave, hot plate, and cookware.

Joyful Escape | The Negroni Suite

Stay in the heart of Upper King Street in this newly renovated 1-bedroom, 1-bath apartment, perfect for couples or solo travelers. You’ll be steps from Charleston’s best restaurants, bars, and historic sights, making it easy to experience the city like a local. Please note this home is located in the lively nightlife district, so some ambient noise may be present, ideal for guests who want to be close to the action! Permit Number: 05770