Family-friendly holiday rentals in Madison County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Madison County

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Superhost

Chalet in Wilmore

4.91 out of 5 average rating, 138 reviews

Timberframe on Farm Lexington, KY Solar Power

Our home and farm is very secluded and overlooks the KY River situated on the top of the Palisades. Minutes from Lexington, Keeneland, Shaker Village, Bluegrass Airport and the Bourbon Trail 5 bedrooms, vaulted ceilings, a 3000 SF home with screened porch and a hot tub. We have a good layout for wheelchairs and a portable wheelchair ramp if needed. Fire Pit, hot tub and hiking trails available. We use solar power for our energy needs! Our pond has no fish but we can direct u to a place to fish!

Superhost

Home in Lexington

4.94 out of 5 average rating, 731 reviews

Adorable, Clean Lexington Cottage, Convenient to Everything

You'll love this bright, well-decorated home away from home! Located in an OPTIMAL location for all that Lexington and surrounding areas have to offer. Safe neighborhood. Xtra long driveway. Comfy beds. Fully fenced in backyard and large patio-NEW PHOTOS COMING SOON! *IF YOU HAVE MORE THAN 2 PETS, YOU MUST CONFIRM WITH ME BEFORE BOOKING. $40 P/PET FEE BEYOND 2. TOTAL # OF PETS ALLOWED DEPENDS ON TYPE/SIZE. YOU ARE RESPONSIBLE FOR ANY DAMAGE/STAINS TO BEDDING, FURNITURE, LANDSCAPING, ETC...

Superhost

Home in Harrodsburg

4.93 out of 5 average rating, 248 reviews

Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

Superhost

Home in Berea

4.91 out of 5 average rating, 235 reviews

High on Berea

High On Berea is a lovely home that was built in 1938. The home sleeps 4 people. The space includes a kitchen, dining room, bathroom, living room and 2 bedrooms. The master bedroom has a queen bed and the second bedroom has a double bed. Living quarters are on one level with 4 stairs leading into the house and 2 stairs at the curb of house. Parking is available in driveway to the left of the home and in the back yard. City ordnance does not allow parking in front of the house.

Superhost

Bungalow in Lexington

4.91 out of 5 average rating, 244 reviews

Near Downtown, Red Mile, Keeneland, UK

Beautiful bungalow with spacious backyard. 5 minutes to Rupp Arena/downtown, 11 minutes to Keeneland, walking distance to Red Mile, and just minutes from UK. We hope you experience a sense of calm as you enter this clean & soothing space. Sleeps 4 comfortably plus one adventurous 5th wheel who doesn't mind a couch bed. Plenty of parking, new LVP flooring, and a new privacy fence in back yard. ROKU TV, basic kitchen amenities, and a washer and dryer on site. License: 15063217

Superhost

Guest house in Lancaster

4.99 out of 5 average rating, 201 reviews

Wishing Well Guesthouse On The Lake

A peaceful, waterfront guesthouse in a serene quiet neighborhood. On 2 acres of rolling hills, this choice location will be a peaceful getaway. Updated furnishings and appliances in this beautiful, open concept living space with a gas fireplace inside or a rustic fire pit outside. Close to lake marina rentals. #Center College #Pioneer Playhouse #Brass Band Festival #Pasture at Marksbury Farm #KY BBQ Festival #Bourbon Trail #Norton Center For The Arts #127 yard sale

Superhost

Home in Berea

4.95 out of 5 average rating, 619 reviews

Traveler's Cottage

Beautiful Craftsman style Bungalow in the heart of Berea. This two bedroom, two bath cottage has off street parking and is a short walk to Artisan Village/Old Town, galleries, shoppes, and cafes. Step into a beautiful, comfortable, clean environment featuring original art, hardwood floors, tall ceilings, queen sized beds. Basic TV channels, Roku, and High Speed Internet. Walk to Nightjar dinner, Native Bagel for breakfast or an early lunch. Great neighborhood!

Superhost

Home in Lexington

4.97 out of 5 average rating, 238 reviews

Bell Ct-133 N Ashland Ave-Horse Park-Bourbon Trail

A great home if you are coming to KEENELAND, THE HORSE PARK, BOURBON TRAIL, or a WEDDING. 5 Star reviews say it all! Located at 133 N Ashland in historic Bell Court, only 5 minutes to DOWNTOWN LEXINGTON, 7 minutes to RUPP ARENA, 6 minutes to UK & UK's football stadium. Close to restaurants, shops, brewery, incl.the trendy areas of Chevy Chase & National Avenue. Walk to many of these places . Great place to stay if you are here for work.

Superhost

Cabin in Stanton

4.89 out of 5 average rating, 266 reviews

100 Acre Preserve | Private Hiking | Creek & Pond

100+ acre private preserve & surrounded by 65K acres of National Forest connected to RRG. Private hiking trail to Sunset Point overlook. Creek meandering entire property with fossil rocks and swimming holes. 1/2 Acre Pond with fishing (Catfish & Bass) & onsite Kayaks & Paddleboard Endless space for outdoor recreation. KIDS: Foosball table. Just 15 minutes from Red River Gorge.

Superhost

Flat in Frankfort

4.87 out of 5 average rating, 348 reviews

Ky Bourbon and Horses-300YD from BT Distillery

Our beautiful 2 bedroom apartment is the closest Airbnb rental you will find to Buffalo Trace Distillery! Conveniently located just blocks from Historic Downtown Frankfort and it's attractions. We are just minutes from the Old and New State Capitols and situated just 300yards from Buffalo Trace Distillery (infamous to "The Kentucky Bourbon Trail").

Superhost

Home in Lexington

4.91 out of 5 average rating, 527 reviews

The Cottage @ Castlewood Park

Charming 3 bed/2 bath cottage in the heart of the Castlewood. Approximately 2 miles to downtown center and UK. Walking distance to great cafe's, shops and restaurants. 3 miles off of 75/64, 15 minutes to Keeneland and The Kentucky Horse Park. Enjoy this cozy and updated cottage at Castlewood Park with a completely fenced in back yard!

Superhost

Home in Lexington

4.9 out of 5 average rating, 227 reviews

Launch your Kentucky Adventure Here #15061828-1

This extensively remodeled home is central to everything in Lexington. Whether your adventure is horse racing, the Bourbon Trail, UK sporting events, or just exploring the Lexington area, this family friendly home is the perfect launch pad. Now with an EV Charger so that you can launch your own EV adventure.