Family-friendly vacation rentals in Shelbyville

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Top-rated family-friendly rentals in Shelbyville

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

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Guest favorite

Home in Louisville

4.95 out of 5 average rating, 228 reviews

Highlands Haven Cottage

This luxurious and charming 1 bedroom home in the prime area of Louisville and The Highlands, is walking distance to the Douglass Loop area of shops and dinning, the Bardstown Rd corridor of shops and dinning and more starts at The Loop, as well as the locally famous Farmers Market on Saturday mornings! This 800 sf fully furnished home features 1 bedroom, 1 bath, a large & bright family room, and a fully outfitted kitchen, is literally minutes to lots of local amenities, dining, shopping, etc!

Jul 10 – 17

G$24,794 GYD per night

Guest favorite

Apartment in Louisville

4.98 out of 5 average rating, 250 reviews

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

Aug 6 – 13

G$23,848 GYD per night

Guest favorite

Farm stay in Springfield

4.98 out of 5 average rating, 604 reviews

The Getaway in Bourbon Country... with Breakfast

Located in the heart of the Bourbon Trail. Come and enjoy the peace and quiet of country living, but still close enough to cities. Breakfast is provided every morning. When you first arrive you will find the entrance on a large covered patio. There is a gas grill there for your use. We also have a fire pit, so bring wood. Feel free to take a walk down to the river at the bottom of our property. There you will find a park like setting where you can relax and listen to nature if you like.

Mar 13 – 20

G$26,190 GYD per night

Guest favorite

Home in Harrodsburg

4.93 out of 5 average rating, 205 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

Oct 7 – 14

G$21,639 GYD per night

Guest favorite

Guest suite in Louisville

4.98 out of 5 average rating, 180 reviews

Spacious Lower-Level in Quiet Neighborhood

This is a spacious, walk-out lower level with a private entrance. Our quiet neighborhood is 1 1/2 miles from I-265, which means easy access to Louisville or beyond the city to bourbon country. It has a large living area and a fully equipped kitchen. Adventure lovers will like being 5 miles from The Parklands. Downtown Louisville is 20 minutes away. The space has 1 queen bed, 1 double bed, and twin bunk beds. It sleeps 5-6 comfortably. We live upstairs so we are available if needed.

Jun 23 – 30

G$28,928 GYD per night

Guest favorite

Guesthouse in Louisville

4.96 out of 5 average rating, 666 reviews

Germantown Carriage House w/garage

Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. This newly constructed carriage house has all the amenities for any length of stay, including garage parking with room for bikes or kayaks. Only 2 miles from downtown Louisville, Germantown is nestled between the energetic and historic Highlands neighborhood, beautiful historic Old Louisville, and hipster NULU. Keyless entry makes for seamless check in and out.

Jul 22 – 29

G$17,853 GYD per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 113 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Oct 4 – 11

G$25,380 GYD per night

Guest favorite

Loft in Shelbyville

4.99 out of 5 average rating, 127 reviews

Urban Loft Downtown in the heart of Bourbon Trail

"The biggest and most dangerous rental option in downtown Shelbyville, Urban Loft is the best and worst 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

Mar 16 – 23

G$218,844 GYD per night

Guest favorite

Apartment in Mount Washington

4.94 out of 5 average rating, 174 reviews

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.

Feb 3 – 10

G$20,364 GYD per night

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 290 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Jan 13 – 20

G$23,781 GYD per night

Guest favorite

Farm stay in La Grange

4.94 out of 5 average rating, 195 reviews

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.

Dec 15 – 22

G$31,557 GYD per night

Guest favorite

Apartment in Frankfort

4.98 out of 5 average rating, 406 reviews

Inviting Downtown Guest Suite

Historic downtown guest suite with modern amenities located in the heart of the capital city. Within blocks of great dining, shopping, entertainment, and historic sites. A short distance to Buffalo Trace distillery, Keeneland racetrack and beautiful bluegrass horse country. Conveniently located 30 minutes from Lexington and 50 minutes from Louisville.

Jan 21 – 28

G$27,444 GYD per night