Family-friendly vacation rentals in Bourbon County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Bourbon County

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

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Guest favorite

Loft in Lexington

4.94 out of 5 average rating, 477 reviews

UNIQUE!! 1BR Loft-Rupp-Downtown w/ Many Extras.

One BR & bath downtown. * Front patio & secluded balcony * Covered parking * Complete kitchn. w/ m-wave, dishwasher, etc. * Cable-TV * B-band Internet * A/C * 24hr arrival access * Security * Desk & supplies * Wshr/Dryer * Guide to area provided with marked map * Self-guided walking tours supplied * Reading library * 15 min. to Keeneland & to Horse Park * 1.3 miles to UK * 1/2 mile to Rupp (10 minute walk) * Walk to restaurants, attractions Always professionally cleaned after each guest leaves.

Guest favorite

Rental unit in Lexington

4.95 out of 5 average rating, 239 reviews

Cute apt. 2 bedroom 3 min to Downtown & District

PLEASE READ (and put in the correct number of guests to the right). Your space is the UPSTAIRS in my comfy cape cod style home. You have a private entrance from the front door. Tastefully appointed with enough room for 1- 3 guests. There is a small frig, microwave, Keurig w/cups, etc., in the kitchenette area in the 2nd bedroom. The mattresses are Casper and Hampton Inn. Only 8 minutes to Keeneland or the Bluegrass Airport. Fifteen minutes to the Horse Park. Very close to U.K. and downtown.

Guest favorite

Townhouse in Lexington

4.89 out of 5 average rating, 434 reviews

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

Guest favorite

Home in Lexington

4.94 out of 5 average rating, 709 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

Home in Harrodsburg

4.93 out of 5 average rating, 236 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

Guesthouse in Wilmore

4.96 out of 5 average rating, 149 reviews

Coach House at the 1898 Red Bud B & B

Lovingly renovated coach house unit was originally the workshop attached to the back of the coach house. It is a ground floor accommodation with private entrance located behind the main bed & breakfast. We are only two city blocks from Asbury! We make a perfect base to explore the area. The Bourbon Trial, numerous horse farm tours, vineyards, Keeneland, the Horse Park, and historic sites such as Shaker Village of Pleasant Hill. Only 11 miles from Lexington.

Guest favorite

Home in Lexington

4.84 out of 5 average rating, 491 reviews

Silver Streak Equestrian Horse Haven

Step out your front door to see beautiful pastures where you can take your coffee and walk to greet the horses. Peaceful setting but just five minutes to downtown Lexington. If traveling by plane it just two minutes away. Enjoy a little quaint piece of Kentucky with historical Keeneland racetrack your next door neighbor. Experience Lexington the horse capital of the world on an actual working horse farm. Sorry pool and hot tub not included

Superhost

Condo in Lexington

4.8 out of 5 average rating, 326 reviews

*Gorgeous Hideout | Close to Everything*

Our New- One Bedroom Apartment is conveniently located near University of Kentucky, Transylvania, National Avenue Warehouse District, The Legacy Trail, Restaurants, Fine Dining & Nightlife. Martine's Pastry conveniently located two doors down. Walk-able to nearby yoga studios, Historic Lyric Theater, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Approximately, 5 miles from I-75\I-64.

Guest favorite

Home in Flemingsburg

4.98 out of 5 average rating, 303 reviews

BLUE MOON LODGE- --UNWIND, CONNECT, REFUEL, RELAX!

If you are looking for a absolutely breathtaking, cozy place for just a few days break, or a complete unique, custom vacation for your family, you have found the place. Come and see for yourself what all the 5 star reviews are about. Every now and then you run across a place that just lifts a weight off your shoulders as soon as you open the door, THE BLUE MOON IS THAT PLACE!!!

Guest favorite

Rental unit in Georgetown

4.91 out of 5 average rating, 176 reviews

Downtown Georgetown Historic Hotel Stay

This newly renovated Downtown Georgetown, KY Apartment is in an historic building located on the Courthouse Square in Downtown Historic Georgetown and within walking distance to restaurants, bars, antique shops, a variety of unique boutiques and more. -7 miles to Horse Park -14 miles to Lexington -17 miles to Keeneland -39.1 miles to Ark Encounter

Guest favorite

Loft in Lexington

4.97 out of 5 average rating, 324 reviews

Treetops Solar Sanctuary

Colorful, light-filled,solar-powered studio apartment within walking distance of the UK campus, football stadium, medical center, arboretum and the Chevy Chase area. Also nearby is downtown Lexington, with its many restaurants and bars. The apartment has a kitchenette with no stove, but with a microwave, toaster and mini-fridge. STR #15085005

Guest favorite

Home in Lexington

4.91 out of 5 average rating, 516 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!