Family-friendly vacation rentals in Lexington

4.91 out of 5 average rating, 138 reviews

Chalet in Wilmore

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!

4.94 out of 5 average rating, 730 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...

4.93 out of 5 average rating, 247 reviews

Home in Harrodsburg

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

4.91 out of 5 average rating, 234 reviews

Home in Berea

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

4.99 out of 5 average rating, 201 reviews

Guesthouse in Lancaster

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

4.95 out of 5 average rating, 618 reviews

Home in Berea

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!

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.

4.93 out of 5 average rating, 226 reviews

Home in Frankfort

Charming South Frankfort Cottage!

Great private guest house in the heart of South Frankfort! Only a 5-10 minute walk to all the Historic Downtown Frankfort and the Kentucky Capitol. Great location for the Bouron Trail (especially Buffalo Trace and Woodford Reserve) and the KY River. We are also close to Keeneland and the Horse Park. Come enjoy what our community has to offer! We pride ourselves in hosting families and friends who want an affordable place to stay!

4.94 out of 5 average rating, 107 reviews

Bungalow in Frankfort

Not So Rustic Cabin Near Elkhorn Creek.

Nice home near many distilleries and Elkhorn Creek. Fully furnished, with washer/dryer. If you’re in town for work or play this house has it all. Also located in the heart of horse country. If outdoor entertainment is what you enjoy then we are close to mountain bike trails, Kentucky river, hiking and rock climbing or my personal favorite canoe/kayaking Elkhorn Creek. Kitchen remodeled in 2025.

4.91 out of 5 average rating, 526 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!