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Family-friendly vacation rentals in Madison County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Madison County

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

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Cabin in McKee

4.9 out of 5 average rating, 204 reviews

Arthur Lakes Log Cabin

Set in the heart of the Daniel Boone National Forest the Arthur Lakes Log Cabin is both easy to get to and relatively secluded. Nestled in a small valley, this quaint cabin is a perfect mountain getaway. Built in 1890, by the Lakes family, it has a romantic, rustic and nostalgic feel. If you are a history buff, interested in Appalachian culture, or just want a charming, outdoorsy and secluded getaway, this cabin is for you. After making your reservation, be sure to check out the "House Manual".

Cottage in Lexington

4.94 out of 5 average rating, 704 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.

Townhouse in Lexington

4.89 out of 5 average rating, 431 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.

Home in Berea

4.92 out of 5 average rating, 691 reviews

Berea Painter's Cottage

Eclectic, clean, comfortable cottage featuring original artwork, located in walking distance of Berea College Campus, Artisan Village/Old Town area, Art Galleries, Unique Shops, The Lot, Rebel Rebel, Nightjar, Sunhouse Craft, and Native Bagel. A short drive to the Pinnacles and Kayaking at Owsley Fork Lake. The location is great. A cozy patio in front of the home with a swing and a tree canopied deck in back that feels like being in a treehouse. Basic TV channels and high-speed internet.

Guest suite in Nicholasville

4.93 out of 5 average rating, 254 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.

Home in Harrodsburg

4.94 out of 5 average rating, 232 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

Home in Berea

4.91 out of 5 average rating, 227 reviews

High on Berea

High On Berea is a lovely home that was built in 1938. The home sleeps 4 people. The space includes a kitchen, dining room, bathroom, living room and 2 bedrooms. The master bedroom has a queen bed and the second bedroom has a double bed. Living quarters are on one level with 4 stairs leading into the house and 2 stairs at the curb of house. Parking is available in driveway to the left of the home and in the back yard. City ordnance does not allow parking in front of the house.

Guesthouse in Lancaster

4.98 out of 5 average rating, 192 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

Guesthouse in Wilmore

4.96 out of 5 average rating, 148 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.

Home in Lexington

4.84 out of 5 average rating, 488 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

Farm stay in Irvine

4.96 out of 5 average rating, 196 reviews

Cottage on the Hill at Harmony Hollow

Cottage on the Hill at Harmony Hollow is surrounded by nature and quiet in beautiful Red Lick Valley. Hike 250 acres of deep woods in pure solitude, go rock hunting in the creek or mushroom hunting in the hills, watch horses on the property peacefully grazing, enjoy the view from the fish pond, or just take solace in the peace and quiet of the cottage.

Home in Nicholasville

4.98 out of 5 average rating, 103 reviews

Cuttawa House

Find your home away from home at Cuttawa House, a luxurious three bedroom home, perfectly appointed. Featuring woodwork harvested directly from the property, dramatic gas fireplace, and an outdoor living room, the Cuttawa House offers both the solitude and peace of the bordering woods as well as beautiful views of rolling horse fields.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Madison County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cabin in Stanton

4.64 out of 5 average rating, 14 reviews

Hot Tub & WiFi - Intimate Cabin - Snuggle Inn

Cabin in Stanton

4.82 out of 5 average rating, 17 reviews

Hot Tub & WiFi - ManeStay - Red River Gorge KY

Cabin in Lexington

5 out of 5 average rating, 26 reviews

Indoor & Outdoor! Spacious & Cozy Cedar Home!

Chalet in Wilmore

4.91 out of 5 average rating, 133 reviews

Timberframe on Farm Lexington, KY Solar Power

Cabin in Stanton

4.67 out of 5 average rating, 21 reviews

Hot Tub & WiFi - Cozy Canopy - Red River Gorge KY

Home in Lexington

4.94 out of 5 average rating, 151 reviews

Hot Tub | Walk to Downtown | Patio | Fire Pit | Ga

Cabin in Stanton

4.5 out of 5 average rating, 167 reviews

Chestnut Cabin: 1BR w/ Hot Tub

Farm stay in Georgetown

4.81 out of 5 average rating, 70 reviews

Horse Heaven! Farm stay in Lexington

Family- and pet-friendly home rentals

Townhouse in Lexington

4.83 out of 5 average rating, 335 reviews

LEXINGTON, KY's Ultimate Chill Spot

Home in Lexington

4.97 out of 5 average rating, 227 reviews

Bell Ct-133 N Ashland Ave-Horse Park-Bourbon Trail

Home in Berea

4.9 out of 5 average rating, 59 reviews

Martin House at Happiness Hills Farm

Bungalow in Lexington

4.93 out of 5 average rating, 43 reviews

Bungalow Bill's - Pet Fee Additional Charge

Condo in Lexington

4.8 out of 5 average rating, 324 reviews

*Gorgeous Hideout | Close to Everything*

Home in Lexington

4.9 out of 5 average rating, 203 reviews

Your Home Away from Home

Guest suite in Lexington

4.9 out of 5 average rating, 219 reviews

New construction Urban Studio

Home in Lexington

4.91 out of 5 average rating, 88 reviews

University of KY/hospital area-#15082674-1

Family-friendly home rentals with a pool

Rental unit in Lexington

4.49 out of 5 average rating, 59 reviews

Furnished 1-Bedroom Apartment: Southeast Lexington

Rental unit in Lexington

4.63 out of 5 average rating, 62 reviews

Furnished 1-Bedroom Apartment: Southwest Lexington

Villa in Paris

4.88 out of 5 average rating, 80 reviews

Barr House Inn-historic 18 miles to LexKY/HorsePK

Condo in Lexington

5 out of 5 average rating, 98 reviews

Luxe - Your Bourbon Trail Adventure Starts Here

Rental unit in Lexington

4.48 out of 5 average rating, 73 reviews

Furnished 2-Bedroom Apartment: Southwest Lexington

Home in Wilmore

4.92 out of 5 average rating, 13 reviews

The Hardin House

Condo in Lexington

4.99 out of 5 average rating, 88 reviews

The Retreat - Bluegrass Country Starts Here

Guest suite in Wilmore

4.94 out of 5 average rating, 265 reviews

The Roosting Place

Destinations to explore