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

Chalet in Wilmore

4.91 out of 5 average rating, 135 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

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

Condo in Lexington

4.89 out of 5 average rating, 267 reviews

*New Downtown Apartment*

One Bedroom Apartment in Downtown Lexington. Enjoy a walk on the Legacy Trail or grab a bite to eat at one of the many restaurants in Downtown Lexington. Our One Bedroom Apartment is conveniently located near University of Kentucky, Transylvania, Legacy Trail, Restaurants, Fine Dining & Nightlife. Walkable to nearby yoga studio, Lyric Theatre, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Martine's Pastry next door is perfect for your morning wake up. Approximately, 5 miles to I75/64.

Guest favorite

Cottage in Lexington

4.94 out of 5 average rating, 718 reviews

Little House Dwntwn - Close to Rupp & Restaurants

1 BR, 1 bath, restored house on quiet street in downtown. Patio (with umbrella), & front porch - each with table & chairs, Off-street parking, TV in Living Room and in Bedroom, Broadband Internet, Cntl A/C, Complete kitchen w/microwave, refrigerator - freezer, toaster oven, regular oven and stove, flatware, dishes and cooking utensils, dishwasher, and washer-dryer. 15 min. to Keeneland or Horse Park. 1.5 miles to UK. 1/2 mile to Rupp (10 minute walk.) Walk to many restaurants and attractions.

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, 238 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, 493 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

Guest favorite

Home in Flemingsburg

4.98 out of 5 average rating, 305 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

Superhost

Home in Lexington

4.92 out of 5 average rating, 513 reviews

Purple Door, Tiny House

Centrally located on a double dead-end street, my quaint and charming little house is perfect for couples or small families! Just a 10-minute drive from downtown, Hamburg Pavilion, or the interstate, it's easy to access all that Lexington has to offer. We are pet-friendly with a $40 pet fee.