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Family-friendly holiday rentals in Shelbyville

Find and book unique family-friendly homes on Airbnb

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 $128 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,210 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Shelbyville holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Shelbyville rentals

  • 4.9 Average rating

    Shelbyville stays are highly rated by guests—averaging 4.9 out of 5!

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 favourite
The spacious living area showcases original wooden beams and exposed brick walls. A round plush couch surrounds a glass coffee table, while a projector hangs above for movie nights. The vibrant area rug adds a cozy touch to the open layout.
Loft in Shelbyville

Close to Buffalo Trace/Transpo available-Must See

Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

4.98 out of 5 average rating, 124 reviews
Guest favourite
An inviting outdoor space features a spacious in-ground pool surrounded by a decorative fence. Lush green trees provide shade, while the backdrop showcases a sunset sky with soft purple hues. Comfortable lounge chairs are positioned near the water, enhancing the area's relaxing ambiance.
Home in Mount Washington

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

4.99 out of 5 average rating, 107 reviews
Top Guest favourite
A paved driveway stretches into the distance, flanked by lush green grass and a large tree. Wooden fencing borders the property, offering views of rolling hills and a colorful sunset sky above.
Farm stay in Frankfort

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & campfires.

4.99 out of 5 average rating, 171 reviews
Top Guest favourite
A spacious living area features large windows allowing natural light to fill the room. A comfortable couch and a reclined chair offer seating, with a coffee table in front. A fireplace serves as a focal point, framed by decorative elements and bookshelves.
Home in Louisville

Home near the Highways

Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

4.96 out of 5 average rating, 322 reviews
Top Guest favourite
A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.
Train in Lawrenceburg

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!

4.99 out of 5 average rating, 595 reviews
Guest favourite
A circular fire pit area is surrounded by six blue Adirondack chairs, positioned on a green lawn. The cabin, featuring a green metal roof and wooden exterior, is visible in the background among tall trees and open space.
Cabin in Shelbyville

Cabin with spectacular views, creek, & hot tub

Located on beautiful Brashears Creek in the heart of Bourbon Country, this loft style cedar cabin makes a great central location to visit some local distilleries and wineries. It is also a great place to stay for anyone who might be in the area for a horse show or interested in antique shopping along Shelbyville's historical Main Street. My personal favorite thing to do at the cabin is enjoy the creek. The water level fluctuates significantly depending on the amount of rainfall received.

4.94 out of 5 average rating, 112 reviews
Top Guest favourite
Home in Lawrenceburg

Bourbon Speakeasy 6BR Estate · Hot Tub · Sleeps 14

Bourbon Trail Hideaway – Where Luxury Meets Fun Gather your favorite people and settle into this stunning 6-bedroom, 4.5-bath modern farmhouse, built for connection, comfort, and fun. With room for up to 14 guests, enjoy spacious living areas, relaxing spa amenities, and entertainment everyone will love. Whether you’re here for the Bourbon Trail or simply to unwind together, this home delivers an unforgettable stay. 🥃 Reserve your dates today and make it a trip to remember.

5.0 out of 5 average rating, 120 reviews
Top Guest favourite
A comfortable living area features a neutral-colored sofa and a wooden coffee table. A ceiling fan hangs above, while a television is mounted on the wall above a decorative fireplace. Natural light enters through two windows, complemented by rustic wall accents.
Guesthouse in Shelbyville

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 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.

4.97 out of 5 average rating, 148 reviews
Top Guest favourite
Dome in Mount Washington

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.

4.98 out of 5 average rating, 264 reviews
Top Guest favourite
A stylish living area features a modern gray sofa accompanied by two blue accent chairs. A large flat-screen TV is mounted above a black fireplace. Natural light enters through multiple windows, which frame views of the surrounding greenery, enhancing the room's serene ambiance.
Home in Louisville

Charming Bungalow on 1.5 Acres in Amazing Location

Peaceful. Private. Clean. Comfortable. Convenient. Hummingbird is a charming updated bungalow in one of Louisville's most coveted neighborhoods. Nestled on 1.5 acres of a historic street, you'll enjoy a park-like setting teeming with wildlife. Private, yet offering easy access to shopping, dining, entertainment, and major highways, this hidden gem is sure to please. Whether here work, fun, or both, you’ll love your time at Hummingbird.

4.98 out of 5 average rating, 138 reviews
Top Guest favourite
The interior of the Airstream showcases a modern layout with a cozy dining area featuring a dark table and beige seating. A spacious bed is visible in the background, complemented by neutral tones and warm lighting. Large windows allow natural light to fill the space.
Campervan/RV in Louisville

The GiGi Airstream, Lakeside at Progress Park

This Gigi is a 2022 Airstream Flying Cloud w/ all the bells and whistles. Everything you need is already here. Perfect for groups, families, or midweek getaways. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

5.0 out of 5 average rating, 167 reviews
Top Guest favourite
A front porch is featured, constructed of wood, with a round table set for four. Decorative flowers are arranged in a vase at the center. Sunlight filters through the open roof, illuminating the surrounding greenery visible beyond the railing.
Farm stay in La Grange

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.

4.95 out of 5 average rating, 806 reviews

Popular amenities for Shelbyville family-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Superhost
Home in La Grange

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

4.91 out of 5 average rating, 142 reviews
Top Guest favourite
A log cabin is set against a vibrant sunset, highlighting its wooden exterior and spacious porch. Lush green grass surrounds the cabin, complemented by flower beds and gravel pathways. The rear showcases windows and entrance doors that invite natural light into the home.
Cabin in Frankfort

Sip on bourbon in the hot tub! +hiking & game shed

5.0 out of 5 average rating, 163 reviews
Guest favourite
A two-story cottage is situated against a lush green backdrop. The exterior features light-colored siding, a covered porch, and multiple windows that allow natural light. A well-maintained lawn surrounds the home, enhancing the inviting appearance of the property.
Cottage in Taylorsville

The Gathering Place

4.94 out of 5 average rating, 191 reviews
Top Guest favourite
The exterior of the remodeled house is framed by lush trees, showcasing a welcoming deck with ambient lighting. A traditional barrel sauna is positioned nearby, blending with the natural surroundings. The inviting façade reflects warm tones, enhanced by the soft glow of the setting sun.
Home in Frankfort

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

4.99 out of 5 average rating, 135 reviews
Top Guest favourite
Home in Bagdad

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

4.98 out of 5 average rating, 164 reviews
Top Guest favourite
Home in Midway

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

4.99 out of 5 average rating, 115 reviews
Superhost
The exterior of the cottage features a charming façade with a covered porch framed by light-colored wood columns. A vibrant red door serves as a focal point, complemented by neatly trimmed shrubs and a landscaped area. Soft, natural lighting enhances the welcoming atmosphere.
Home in Taylorsville

Little Slice of Heaven-27

4.83 out of 5 average rating, 105 reviews
Top Guest favourite
A charming bungalow exterior is highlighted by vibrant green siding and white accents. A covered porch with intricate railing invites guests, while a pathway leads through well-maintained landscaping adorned with flowers and fresh grass. The setting sun casts a warm glow over the home.
Home in Frankfort

River Row Bungalow

4.96 out of 5 average rating, 136 reviews

Family- and pet-friendly home rentals

Top Guest favourite
A welcoming living area features a light blue wall and hardwood floors. A large sectional sofa is positioned next to a coffee table. A clock adorns the wall, and recessed lighting illuminates the space. The adjoining area includes a dining table visible in the background.
Home in Louisville

Newly Renovated Derby House

4.99 out of 5 average rating, 220 reviews
Top Guest favourite
A two-story brick home is set among lush green landscaping, featuring a welcoming front porch. Large windows allow for ample natural light, while a manicured lawn and mature trees frame the property, creating a serene outdoor setting.
Home in Frankfort

Large Family Gatherings and Bourbon Tours

4.95 out of 5 average rating, 137 reviews
Top Guest favourite
The farmhouse is set against a vibrant sunset, illuminating the sky with shades of orange and pink. The white two-story structure features a welcoming porch, surrounded by lush green grass and a rural landscape.
Farm stay in Simpsonville

Farm House - near Bourbon Trail & Pet Friendly

4.89 out of 5 average rating, 102 reviews
Top Guest favourite
A charming exterior view of a two-story bungalow features blue-green siding and a welcoming front porch. American flags are displayed, while flower beds with various plants enhance the landscaped front yard. The stone walkway leads to the entrance, inviting visitors to approach the home.
Home in Frankfort

The Crafty Bourbon Bungalow Apartment

4.98 out of 5 average rating, 110 reviews
Top Guest favourite
A blue carriage house is viewed from the driveway, surrounded by greenery and blooming trees. Steps lead to an upper balcony, offering outdoor potential. The driveway provides easy access to the garage, emphasizing a sense of space and privacy.
Guesthouse in Louisville

HIghlands Modern Get Away

4.92 out of 5 average rating, 1255 reviews
Top Guest favourite
Cabin in Shepherdsville

Bourbon Cabin - Speakeasy/HotTub/Arcade/Derby

4.98 out of 5 average rating, 125 reviews
Guest favourite
A spacious living area is equipped with a large sectional sofa and a wooden coffee table, providing a comfortable gathering space. The modern kitchen features stainless steel appliances and dark cabinetry, while an open layout invites natural light from the adjacent windows.
Home in Germantown

The Caldwell Highlands/Germantown

4.94 out of 5 average rating, 202 reviews
Top Guest favourite
An exterior view of the charming upstairs unit is presented, showcasing a wooden staircase leading to a covered porch. The building features a brick facade, with greenery surrounding the entrance. A cloudy sky is viewed above, giving a subdued ambiance.
Barn in Midway

Modern horse barn

4.98 out of 5 average rating, 164 reviews

Family-friendly home rentals with a pool

Top Guest favourite
Two horses are depicted, one dark brown and the other light chestnut, standing side by side. They are adorned with riding gear, their eyes focused on the landscape ahead, which features rolling hills blanketed in greenery and autumn foliage.
Farm stay in Harrodsburg

The Bunkhouse at Big Red Stables

4.96 out of 5 average rating, 164 reviews
Top Guest favourite
An inviting open kitchen showcases modern appliances and a spacious countertop, perfect for meal preparation. A cozy living room features a plush sofa, complemented by natural light from nearby windows and tasteful decor that enhances the comfort of the space.
Home in Prospect

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

5.0 out of 5 average rating, 131 reviews
Top Guest favourite
A living area features comfortable seating arranged around a wooden coffee table. A stone fireplace with an electric insert is positioned beneath a flat-screen television mounted on the wall. The warm red walls create a cozy backdrop, and kitchen facilities are visible in the background.
Cottage in Taylorsville

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

4.99 out of 5 average rating, 155 reviews
Guest favourite
A living area features a dark leather sofa and two tufted chairs positioned around a circular wooden coffee table. A large piece of wall art and patterned curtains add visual interest. Natural light enters through the window and door leading to a small balcony.
Apartment in Central Business District

4th Street Suites - Stunning King Bed Suite

4.95 out of 5 average rating, 206 reviews
Guest favourite
Home in Taylorsville

#18 Kentucky Sunrise - Lakefront Home with spacuio

4.89 out of 5 average rating, 138 reviews
Guest favourite
Cottage in Taylorsville

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

4.91 out of 5 average rating, 149 reviews
Guest favourite
A hot tub is illuminated with blue LED lights, creating a serene atmosphere in a cozy corner. The tub features multiple seating positions and control buttons for easy adjustments. A wooden bench is placed nearby, offering a place to relax before or after use.
Home in Lawrenceburg

Restful Bourbon Trail Lodge with Pool and Hot Tub

4.82 out of 5 average rating, 181 reviews
Top Guest favourite
A spacious living and dining area features a full-sized, counter-height dining table with six chairs. A cozy seating area includes a sofa and a secondary sleeping area with a twin bed and trundle. Decorative shelving displays various kitchenware and the room is softly illuminated by natural light.
Farm stay in Georgetown

Beautiful farm stay apartment, rural Georgetown KY

4.97 out of 5 average rating, 190 reviews

When is the best time to visit Shelbyville?

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Avg. price$315 AUD$293 AUD$323 AUD$428 AUD$464 AUD$358 AUD$353 AUD$351 AUD$353 AUD$391 AUD$313 AUD$311 AUD
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Destinations to explore