Family-friendly vacation rentals in Woodford County

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Top-rated family-friendly rentals in Woodford County

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

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Guest favorite

Chalet in Wilmore

4.9 out of 5 average rating, 136 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!

Guest favorite

Home in Lexington

4.94 out of 5 average rating, 718 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...

Guest favorite

Guest suite in Nicholasville

4.93 out of 5 average rating, 257 reviews

Moonlit Meadows: A Kentucky Getaway for Travelers

Escape to the heart of Kentucky's countryside in our modern guest suite, set across a 17-acre landscape. Immerse yourself in the serenity of nature with views of a pond and beautiful rolling fields. Ideal for both business and leisure travelers as well as those visiting Asbury University. Our guest suite has continued to offer a tranquil haven where you can relax and rejuvenate! Visit the great grandson (“Sportacular”) of the legendary Secretariat. He is an OTTB residing on our farm.

Guest favorite

Home in Lexington

4.84 out of 5 average rating, 171 reviews

Silver Streak Ranch - Horse Hideaway

Enjoy staying in cute farmhouse with lots of historic horse racing memorabilia that articulates charming horse country feeling. Only 10 minutes from downtown Lexington and University of Kentucky. Don't forget one of Lexington historical designation, Keeneland Racetrack right next door. This is a working horse farm where you could wake up looking out the kitchen window to horses and donkey. Parking is no problem plus fenced in area for dogs along with acres of fields to walk your pets.

Guest favorite

Home in Harrodsburg

4.93 out of 5 average rating, 241 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

Guest favorite

Bungalow in Lexington

4.91 out of 5 average rating, 242 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

Guest favorite

Guesthouse in Lancaster

4.98 out of 5 average rating, 197 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

Guest favorite

Guesthouse in Frankfort

4.99 out of 5 average rating, 115 reviews

Treetop Hideaway

Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

Guest favorite

Home in Lexington

4.97 out of 5 average rating, 233 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.

Guest favorite

Home in Frankfort

4.93 out of 5 average rating, 223 reviews

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!

Guest favorite

Bungalow in Frankfort

4.94 out of 5 average rating, 105 reviews

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.

Guest favorite

Home in Lexington

4.91 out of 5 average rating, 522 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!