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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 $152 NZD 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, Wifi 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.

Indoor spacesKitchenTV

4.98 out of 5 average rating, 123 reviews
Top Guest favourite
Home in Shelbyville

Bourbon, Bridles & Birdies Retreat

We would LOVE to welcome you to Bourbon, Bridles & Birdies Retreat! Nestled in a quiet & peaceful neighborhood in the historic district of downtown Shelbyville, this FAMILY-FRIENDLY home offers unique dining experiences, seriously good shopping & the fairgrounds less than a mile walk away. Do you have plans in the big city?This thoughtfully laid out, detail-packed home will be your perfect retreat to relax. Please see "The Space" section for all the amazing attractions Shelbyville has to offer!

Indoor spacesKitchenSleep quality

5.0 out of 5 average rating, 22 reviews
Top Guest favourite
A cozy front porch features woven chairs arranged around a small table, inviting relaxation. Lush green ferns are placed in terracotta pots, complementing the rustic wooden beams and the log cabin's natural surroundings.
Cabin in La Grange

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin 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. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

KitchenFamilyAccess

4.97 out of 5 average rating, 138 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!

Indoor spacesFamilyPool

4.99 out of 5 average rating, 104 reviews
Top Guest favourite
A well-equipped kitchen features dark wooden cabinetry and granite countertops. Four barstools with cushioned seats are arranged around a large island. Stainless steel appliances, including a refrigerator and oven, are visible alongside natural light streaming through a window.
Cabin in Frankfort

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

FamilyKitchenOutdoor spaces

5.0 out of 5 average rating, 247 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!

Indoor spacesFamilyWi-Fi

4.99 out of 5 average rating, 587 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.

Indoor spacesFamilyWalkability

4.94 out of 5 average rating, 112 reviews
Top Guest favourite
A modern cabin exterior features a welcoming front porch with wooden railings and chairs arranged for relaxation. Steps lead from a gravel path to the entrance. The building's dark exterior contrasts with the clear blue sky and grassy landscape surrounding it.
Cabin in Frankfort

The Bourbon Coop

The Bourbon Coop is arguably the best situated location on the Bourbon Trail! It is a convenient walk or golf cart ride to Whiskey Thief distillery across the street. Situated a quarter of a mile off interstate 64, in between Louisville and Lexington, with a 15 minute drive into the city of Frankfort. The cabin is located on a beautiful, scenic plot of land, shared by the friendly hosts, chickens, ducks and a couple of goats. This is a comfortable, quiet and quaint country experience!

Indoor spacesFamilyComfort

4.99 out of 5 average rating, 116 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.

FamilyIndoor spacesView

4.97 out of 5 average rating, 146 reviews
Guest favourite
The spacious living area features large windows allowing ample natural light. Elegant details include high ceilings and exposed brick walls. A plush sofa is arranged around a coffee table, while a dining area with a wooden table is visible in the background.
Loft in Shelbyville

The Lucky Penny Downtown Loft - Central Location!

Experience timeless charm in this beautifully renovated mid-19th century Airbnb in the heart of Shelbyville. With soaring 14 ft ceilings, this historic gem combines classic architecture with modern amenities. Centrally located, it offers convenient access to local attractions, dining, and shopping. Enjoy a blend of elegance and comfort in a space that honors its rich heritage while providing all the contemporary conveniences you need for a memorable stay.

Indoor spacesFamilyLayout

4.92 out of 5 average rating, 52 reviews
Top Guest favourite
A gravel path leads up to the cabin, surrounded by lush greenery and tall trees. The cabin's exterior features a mix of wood and metal siding, with a deck extending from the entrance, providing a connection to the natural surroundings.
Cabin in Lawrenceburg

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.

KitchenIndoor spacesCheckout

4.99 out of 5 average rating, 131 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.

KitchenFamilyLocation

4.98 out of 5 average rating, 259 reviews

Popular amenities for Shelbyville family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
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

FamilyKitchenWi-Fi

4.84 out of 5 average rating, 103 reviews
Superhost
Home in La Grange

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

Indoor spacesFamilyCheckout

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

FamilyKitchenDecor

5.0 out of 5 average rating, 159 reviews
Top Guest favourite
Home in Lawrenceburg

Bourbon Speakeasy 6BR Estate · Hot Tub · Sleeps 14

FamilyKitchenView

5.0 out of 5 average rating, 116 reviews
Top Guest favourite
Home in Bagdad

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

KitchenIndoor spacesHospitality

4.98 out of 5 average rating, 160 reviews
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

FamilyIndoor spacesCleanliness

4.99 out of 5 average rating, 131 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

Indoor spacesKitchenRiver

4.96 out of 5 average rating, 133 reviews
Top Guest favourite
The outdoor space features a DIY pickleball court, surrounded by well-maintained grass and bordered by planters. A gazebo and hot tub are visible adjacent to the brick house, while tall trees provide a serene backdrop to the inviting courtyard area.
Home in Midway

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

FamilyKitchenQuiet

4.99 out of 5 average rating, 114 reviews

Family- and pet-friendly home rentals

Guest favourite
The exterior features a two-story white house with a red front door, surrounded by greenery. A concrete pathway leads to the entrance, and a spacious driveway complements the landscape. Soft outdoor lighting highlights the home's contemporary design during dusk.
Home in Simpsonville

Comfortable sleek home bourbon trail

Indoor spacesKitchenCleanliness

4.91 out of 5 average rating, 148 reviews
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

FamilyIndoor spacesLocation

4.99 out of 5 average rating, 218 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

Indoor spacesKitchenCleanliness

4.95 out of 5 average rating, 137 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

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 107 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

Indoor spacesKitchenShared spaces

4.96 out of 5 average rating, 319 reviews
Superhost
The exterior showcases a historic building with large windows allowing natural light. A welcoming entrance leads to additional outdoor seating. An indoor game area features a shuffleboard table and playful décor. A cozy outdoor space is highlighted by a fire pit, surrounded by modern seating.
Home in Louisville

Best Location in the City-2 Story Patio & Hot Tub

Indoor spacesKitchenNearby

4.92 out of 5 average rating, 296 reviews
Top Guest favourite
A colorful living area is furnished with a patterned sectional sofa and a round glass coffee table. Natural light enters through multiple windows, illuminating the artful wall decor. A kitchenette area with modern appliances is visible in the background, enhancing the space's functionality.
Guest suite in Louisville

Hide away close to everything

FamilyKitchenOutdoor spaces

4.95 out of 5 average rating, 329 reviews
Guest favourite
A wooden sign is displayed on a wall, featuring the text 'Welcome to Our Nest' in an elegant cursive font. The sign has a rustic design with a whitewashed finish, and a pink ribbon is tied at the top for hanging.
Loft in Crestwood

Welcome to the Nest!

KitchenIndoor spacesAir conditioning

4.88 out of 5 average rating, 233 reviews

Family-friendly home rentals with a pool

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!

Indoor spacesFamilyHospitality

4.99 out of 5 average rating, 153 reviews
Guest favourite
A two-story cottage with light gray siding and a symmetrical facade is shown. The front porch features wooden steps leading to an inviting entrance. Lush green hedges frame the exterior, while a gravel driveway extends to the left, emphasizing the cottage's serene setting.
Cottage in Taylorsville

Lake Livin' & Bourbon Sippin'

FamilyKitchenAir conditioning

4.84 out of 5 average rating, 128 reviews
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

FamilyIndoor spacesAmenities

4.96 out of 5 average rating, 164 reviews
Guest favourite
Cottage in Taylorsville

Luxury Retreat with Hot Tub

KitchenIndoor spacesBackyard

4.95 out of 5 average rating, 223 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

KitchenFamilyCheckout

5.0 out of 5 average rating, 130 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

FamilyKitchenAccess

4.82 out of 5 average rating, 180 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

FamilyIndoor spacesHospitality

4.97 out of 5 average rating, 188 reviews
Top Guest favourite
A comfortable living area is furnished with a leather recliner and a wooden coffee table. A television is mounted on the wall opposite the open kitchen, where light cabinetry and seating at the counter are visible. Natural light enters the room, creating a warm ambiance.
Home in Jeffersonville

Cozy Neighborhood Home - 10 min to Louisville!

Indoor spacesKitchenWalkability

4.95 out of 5 average rating, 113 reviews

When is the best time to visit Shelbyville?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$373 NZD$346 NZD$382 NZD$507 NZD$549 NZD$424 NZD$417 NZD$415 NZD$417 NZD$463 NZD$370 NZD$368 NZD
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Destinations to explore