Family-friendly vacation rentals in Anderson County

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Top-rated family-friendly rentals in Anderson 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!

Top guest favorite

A spacious hallway features hardwood flooring, accentuated by light-colored walls and tasteful artwork. Decorative tables showcase floral arrangements, while comfortable seating is arranged nearby. Open doorways lead to inviting rooms, creating a warm and welcoming atmosphere throughout the area.

Home in Bardstown

4.83 out of 5 average rating, 114 reviews

Upscale 1 Story Bourbon Trail XLBeds King 2 Single

UPSCALE 1 STORY HOUSE * 3 BDRM (4 Beds), 2 BATH, OPEN FLOOR PLAN, provides a Great Space to Enjoy time with your FAMILY AND/OR FRIENDS while visiting BARDSTOWN & THE BOURBON TRAIL. Primary Bedroom Suite has XL K/S Sterns & Foster Bed, ensuite Bathroom & walk-in Closet. Large Guest Room Q/S Bed and Dedicated Workspace 3rd Bedroom 2 XL Single Beds, Brand New Top of the Line Beauty Rest Cooks kitchen has all Appliances, cookware & dishware etc. F/S Washer and Dryer. CENTRAL HVAC & HEATING

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 well-lit bathroom features a sink with a beige countertop and a large mirror above. A shower curtain with a floral pattern encloses the shower, while a toilet is positioned beside it. Towels neatly hang on a nearby rack.

Cottage in Taylorsville

4.89 out of 5 average rating, 122 reviews

Best view of the lake two bed two bath cottage #4

Make yourself at home in this cozy 2 bedroom 2 bath lakeside cottage with incredible views of Taylorsville Lake. You will love the open airy feel complete with deck and hot tub. Washer dryer, four beds that easily sleeps 7. TV in both the master bedroom and the living room. The wonderful community also offers a swimming pool and play area for kids. Enjoy the wildlife as well including deer and turkey as you explore the walking trails. We are located in the heart of the bourbon country!

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, 247 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

Top guest favorite

A well-maintained backyard area is highlighted by a green hammock suspended between trees. The brick apartment is elevated with a wooden deck and stairs leading to the entrance. Surrounding the space, manicured shrubs and grass create a peaceful outdoor environment.

Guesthouse in Frankfort

4.99 out of 5 average rating, 117 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.

Top guest favorite

A spacious bed is presented with soft white linens and decorative pillows in warm tones. A wooden bedside table holds a lamp, while a tray with two cups is placed on the bed. A scenic wall art piece features a tranquil lakeside view.

Cottage in Taylorsville

4.96 out of 5 average rating, 194 reviews

KY Derby 50% off - Lake View

Nestled in the Bourbon Trail hills of Kentucky, rests Taylorsville Lakes only waterfront vacation community. Strategically placed; Cottage 37 sits on a ridge that overlooks the 3,050-acre lake and its 10,000 acres of wildlife preserve. The owners tried to capture the view from the kitchen table to inspire the cabins four-season theme. The wall hangings were chosen to mirror Kentucky’s beautiful hills, Derby culture, and the water of Taylorsville Lake.

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-lit open living area features a cozy couch with patterned cushions, accompanied by a dining space. Modern kitchen appliances, including a microwave and refrigerator, are neatly arranged within white cabinetry. Natural light filters in through a round window above the door.

Home in Frankfort

4.93 out of 5 average rating, 226 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

Lush greenery surrounds a serene river, with trees framing the peaceful water. Tall cliffs, textured with layers of rock, rise in the background, showcasing natural beauty and tranquility. The vibrant foliage hints at the diverse plant life in the area, creating a calming outdoor scene.

Bungalow in Frankfort

4.94 out of 5 average rating, 107 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

The spacious living area features a large gray sectional sofa arranged comfortably on a soft area rug. A rustic coffee table sits at the center, surrounded by books and decor. A custom bookshelf is filled with various items and framed photos, complementing the exposed wooden beams overhead.

Loft in Shelbyville

4.99 out of 5 average rating, 134 reviews

Urban Loft Sleeps 16 and close to Buffalo Trace

"The biggest and best rental option in downtown Shelbyville, Urban Loft is the best place to stay in town. It’s an absolutely breathtaking space with enough sleeping space for well over a dozen guests to comfortably cohabitate, but the space is so absolutely picture perfect and secluded that you might have trouble coaxing all your traveling companions to ever leave." - Bourbon Review Magazine