Family-friendly vacation rentals in Bourbon County

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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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Top guest favorite

An airy living space is showcased, featuring large windows that invite natural light and provide views of the surrounding fields. Comfortable seating arrangements with a mix of couches and chairs are positioned around a central area rug, highlighting a handcrafted coffee table and a wood stove.

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!

Guest favorite

The living area features a full-size sofa, two wooden chairs, and a coffee table on a patterned rug. Wall art hangs above the couch, and a dining table for four is situated nearby. Warm lighting complements the neutral walls and wood flooring.

Townhouse in Lexington

4.88 out of 5 average rating, 471 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

A cozy living area features a decorative fireplace with blue tiles and a mounted television above. Comfortable seating includes a light gray chair and a green armchair. A round coffee table is positioned in the center, surrounded by a soft area rug. Natural light enters through two windows.

Home in Lexington

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...

Guest favorite

A welcoming sitting area features a comfortable leather sofa and a patterned rug. Natural light streams through large windows, revealing glimpses of the outdoor greenery. A wooden table and chairs are positioned in the background, alongside a decorative wall clock and various artwork.

Private room in Nicholasville

4.93 out of 5 average rating, 262 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

A modern structure with a gray metal roof is positioned on a grassy area, surrounded by gentle rolling hills. A wooden fence borders the property, leading to an illusion of a calm river and a colorful sunrise in the background, creating a serene countryside scene.

Home in Harrodsburg

4.93 out of 5 average rating, 246 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

An archway leads into a bright, open space featuring a dining table with wooden chairs. A modern kitchen is visible in the background, equipped with white appliances. Natural light filters through curtains, casting a soft glow on the neutral-toned walls.

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

Guest favorite

A welcoming entrance path leads to a quaint brick house adorned with a decorative star. A swing sits under a large tree, while a wooden fence outlines the grassy yard, enhancing the peaceful rural ambiance.

Home in Lexington

4.84 out of 5 average rating, 520 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

Top guest favorite

A well-appointed bathroom is equipped with a granite countertop and a mirrored sink. The shower area features a glass enclosure, and blue towels are neatly hung on fixtures. A patterned tile floor enhances the clean, modern look of the space.

Home in Lexington

4.97 out of 5 average rating, 236 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.

Top guest favorite

A bright corner of the living area features a white bookshelf filled with decorative items and framed pictures. A wooden rocking chair with a colorful cushion sits invitingly nearby. Light from a window creates a warm ambiance on the hardwood flooring.

Home in Flemingsburg

4.98 out of 5 average rating, 321 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!!!

Superhost

A four-person dining table with modern chairs is situated near large glass doors, allowing natural light to fill the space. Outdoor seating is visible through the doors, highlighting a connection to the surrounding landscape.

Cabin in Stanton

4.89 out of 5 average rating, 265 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.

Guest favorite

A well-lit bathroom features warm wood floors and cream-colored walls. A colorful shower curtain adds a lively touch. Essential amenities include a white sink, toilet, and a mirror above the sink. Towels are neatly hung on nearby hooks, ensuring convenience for guests.

Home in Lexington

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!

Guest favorite

A comfortable living area features a navy blue sofa paired with two patterned chairs. A wooden coffee table is centered on a neutral rug, accompanied by decorative items and magazines. Natural light enters through the window, framed by orange curtains.

Home in Lexington

4.9 out of 5 average rating, 226 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.

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What guests are saying

Coach House at the 1898 Red Bud B & B

4.96 out of 5 average rating, 152 reviews1 month ago

Suzann was a great host!! We stayed in the coach home of her bed and breakfast which was perfect for our family of 3. There was a playset with swing, slide, sandbox and pirate ship on top that our son enjoyed. This location was close to all that we did...we stopped at Ark Encounter (we are from Ohio) and had about a 65 min drive to Suzann's place. We went to Kentucky Horse Park which was only 40 minutes away and Shaker Village was only 16 minutes away!! And not to forget about Buc-ee's which is 52 minutes from Suzann :-) Great location, clean and comfortable!!!!!

Guesthouse in Wilmore

What guests are saying

The Cottage

4.96 out of 5 average rating, 77 reviews2 weeks ago

We had a wonderful stay at Steve’s house in Midway. The house is SO charming… even more so than the pictures convey. Perfectly outfitted, totally comfy and the perfect location for a fun weekend of Keeneland racing and Midway dining (be sure not to miss Holy Hill Inn and Heirloom for two of the best dining experiences you’ll ever have!). The location is both convenient and beautifully picturesque. Don’t pass this one up! You won’t regret it!

Home in Midway

What guests are saying

Wickliffe

5 out of 5 average rating, 40 reviews5 months ago

5 stars just isn't enough. Great communication from Steve and Lisa before and during the stay. Quiet peaceful location on a working horse farm, but only 20 minutes to downtown Lexington. Spacious layout was clean and comfortable. Fully apportioned kitchen, enormous master suite, cozy breakfast nook, open living area. Lots of history with modern amenities. Hardwood floors, high ceilings and crown molding along with satellite tv and fast Wi-Fi connection Short walk down the driveway to corrals with several retired and active racehorses. And then there's John-George and Sadie, the absolutely adorable donkeys, the highlight of our stay. Bring treats and you'll have new best friends for the duration of your stay. We will definitely be back.

Home in Paris

What guests are saying

The Historic Lexingtonian

4.96 out of 5 average rating, 53 reviews7 months ago

What a great place to stay in Lexington! Gregory greeted us and showed us around the property and gave us suggestions for activities. The home was exactly as described and perfect for three couples. The bedrooms all had attached bathrooms which makes it really nice for different families to stay there. The bathrooms were clean and well appointed. The kitchen was well stocked with all sorts of pots, pans, dishes, and utensils. While there is a formal dining room we all chose to eat at the kitchen table. We enjoyed using the cozy living room to chat and recap the days' events. Gregory keeps the home spotless. I highly recommend this place for your visit to Lexington.

Home in Lexington

What guests are saying

The Summer Kitchen at Waverly Farm

4.98 out of 5 average rating, 49 reviews6 months ago

Natalies place was perfect for what we needed. Central to all the places we wanted to visit. Very clean. Natalies father Hoppy was a gentleman and explained the history of the farm and even drove us to Ashford Stud Farm since he was going there and showed us the farm which was the highlight of our stay. Please thank him for us. Jim and Donna

Farm stay in Versailles

What guests are saying

3 Bedroom Downtown Townhouse, Close to All!

4.77 out of 5 average rating, 384 reviews1 week ago

10/10 place to stay in Lexington. In a private enclosed parking lot in front of a row of quiet town homes. Felt like a safe area. Easy to walk or drive to restaurants nearby. Comfy beds, and having 2 full bathrooms was great! Lots of towels! Hosts were wonderful in leaving cool recommendations for restaurants nearby. We only had 4 adults here, but with three bedrooms you could comfortably fit 6 adults, 2 in a private bedroom each. No complaints! Would definitely stay again!

Townhouse in Lexington