
Family-friendly holiday rentals in Shelbyville
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Shelbyville
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Walking Bridge, Putt Putt House
NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

Anjuna House - a Scandi riverfront forest getaway
Welcome to the enchanting retreat of "Anjuna," nestled among a sprawling forest in the heart of southern Indiana. This modern 4-bedroom, 3 bathroom luxury cabin features 14' floor-to-ceiling windows, and 1000+ sqft deck! Outside there are 12 acres of forest to explore, an outdoor shower and a tranquil river which meanders through the property. Anjuna is near Knobstone trail, Marengo Cave, and the bourbon trail in Louisville. Bring family, friends or just yourself to relax or explore at Anjuna!

Close to all the popular distilleries Perfect Spot
Ultra Luxury downtown 2 BR loft, spacious enough for 5 adults. Located in quaint Downtown Shelbyville, KY, you are in the heart of the bluegrass near major distilleries and race tracks and close to coffee shops, restaurants and bars right on the same block. You can't go wrong with this unique loft for its decor and proximity to everything. Close to all distilleries on the eastern part of the Trail and centrally located to all distilleries in the state. Come see what this space has to offer

Historic Cabin by Bourbon Trail
Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Bourbon Trail: Caboose on the Farm
Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

The Gathering Place
The Gathering Place is the perfect place to get away and gather with family and friends. The resort is located conveniently between Bardstown, Louisville, and Frankfort on the Bourbon Trail. Offseason hiking, fireplace, and hot tub make a great peaceful getaway or work from "home" experience. Enjoy fishing, boating, kayaking, hiking, bird/deer watching and relaxing. The owners have been Resort guests for years and now own a cottage to enjoy and share with family, friends, and guests.

Cottage of Eden. Bourbon Trail Stay in Shelby Co.
Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Parkside 3 Bedroom apartment
This apartment is in a growing and diverse part of Louisville. It is located in the Shelby Park neighborhood just a few blocks from Old Louisville and a few blocks from Germantown. The house has been recently renovated and it is beautiful. Virtually everything in the apartment is new. The bathroom feels like a spa with a freestanding modern tub and a walk in shower with double shower heads and a tankless hot water heater for unlimited hot water.

Hidden View Cabin
Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

My Old Kentucky Dome
An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Bourbon Country Cabin
Nestled in the Heart of Bourbon Country sitting on 80 acres of Kentucky woodlands this charming loft style cabin makes a great central location to visit all the local distilleries on the Kentucky Bourbon Trail! Enjoy exploring the walking trails, creek, and the property while you stay in a peaceful cabin in the woods! Check out our other listing too if you have a large group and would like to book both rentals. Bourbon Country Cottage

Lux Farmhouse | HotTub | Firepit | GameRm |5 acres
Brand-new luxury farmhouse on 5 private acres in the heart of Kentucky bourbon country. This 4BR retreat sleeps 12 and is built for unforgettable group getaways, with a massive game room, full bar, pool table, shuffleboard, foosball, poker table, 85” TV, covered 6-person hot tub, huge firepit, outdoor games, and a fully stocked chef’s kitchen. Minutes from Buffalo Trace, Bulleit, and Jeptha Creed. Send us a message with any questions!
Popular amenities for Shelbyville family-friendly rentals
Family-friendly home rentals with a hot tub

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Hot Tub Glow Hill Home Near Horse Park and Ark

Romantic country getaway with hot tub

Governor's Private Cabin on Bourbon Trail w HotTub

Work & Unwind | Golf Sim · Pool · Gym · Parking

Bourbon Trail*Tesla EV charger* HOT TUB

The Squirrel's Nest - 3 bed/2 bath with hot tub

Lake Refuge near Louisville & Bourbon Trail #52
Family- and pet-friendly home rentals

HIghlands Modern Get Away

Cottage Retreat at Tiwazzen Farm

*Unique Wooded Cabin*4 beds 20 min from The Ark

Welcome to the Nest!

Highbridge River Cabin, Private Dock, EV Charger

Countryside On the Bourbon Trail, 22 Quiet Acres

The Green House in Downtown

WynDown Spot
Family-friendly home rentals with a pool

The Bunkhouse at Big Red Stables

Lakeside Haven Cottage 4, Lake View, Hot Tub, Pool

Equestrian, Sports Fans, Bourbon Trailers

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

POOL/ game room! 8 beds 2 baths 3 bedrooms

Luxury Retreat with Hot Tub

Cottage on the Bourbon Trail

Come explore Jeffersonville & Louisville
When is the best time to visit Shelbyville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £165 | £153 | £169 | £172 | £198 | £176 | £185 | £184 | £185 | £205 | £164 | £163 |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 7°C | 3°C |
Quick stats about holiday rentals that are family-friendly in Shelbyville

Total holiday rentals
Explore 40 holiday rentals in Shelbyville

Nightly prices starting at
Shelbyville holiday rentals start at £75 per night before taxes and fees

Verified guest reviews
Over 2,050 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Shelbyville holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shelbyville rentals

4.9 Average rating
Shelbyville stays are highly rated by guests – averaging 4.9 out of 5!
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- Family-friendly rentals Kentucky
- Family-friendly rentals United States
- Ark Encounter
- Kentucky Horse Park
- Buffalo Trace Distillery
- Kentucky Exposition Center
- Rupp Arena
- Kentucky Derby Museum
- Kentucky Kingdom & Hurricane Bay
- Louisville Slugger Field
- Churchill Downs
- Louisville Slugger Museum & Factory
- Muhammad Ali Center
- Falls of the Ohio State Park
- Angel's Envy Distillery
- Waterfront Park
- Jefferson Memorial Forest
- Big Four Bridge
- University of Louisville
- Bernheim Arboretum and Research Forest
- Kentucky International Convention Center
- University of Kentucky
- James B Beam Distilling
- Against The Grain Brewery & Smokehouse
- Kentucky Science Center
- Frazier History Museum





