Family-friendly vacation rentals in Shepherdsville

4.9 out of 5 average rating, 113 reviews

An outdoor living space features a hot tub beneath a wooden pergola, with water cascading gently. Comfortable seating is arranged nearby, facing a cozy firepit. Bright orange doors lead to the interior, surrounded by lush greenery and a privacy fence.

Home in Coxs Creek

The Barrel Proof Bungalow

This stylish 3 bedroom 2 bathroom home on the "Kentucky Bourbon Trail" has been a labor of love and full remodel down to the studs. The Barrel Strength Bungalow is centrally located between Interstate 65 (Jim Beam) and Bardstown's city center. A unique outdoor living space with one of a few hot tubs in Bardstown area Airbnb's. Also offers a firepit, outdoor grill and patio area. More than 15 distilleries within an hour's drive and approximately 30-35m to Downtown Louisville and Churchill Downs.

4.97 out of 5 average rating, 103 reviews

Cabin in Shepherdsville

Bourbon Cabin - Speakeasy/HotTub/Arcade/Derby

🏡 Bourbon Trail Hideaway – A spacious 5BR, 3.5BA log cabin on 6 private acres, just 9 mins from Jim Beam! 🍂 Blending rustic charm with modern comforts, this retreat features a Brand NEW speakeasy lounge, hot tub, fire pit, wraparound decks, arcade games, and a well-stocked kitchen. Enjoy breathtaking sunsets, fast WiFi, plush seating, Smart TVs, and a cozy ambiance, plus luxurious beds, spa-like bath, and plenty of space to relax or entertain. Perfect for groups, couples & bourbon lovers! 🥃✨

Superhost

A cozy living area is highlighted by a large, plush bean bag chair and a comfortable sofa. A wall-mounted TV is positioned near a small table. Light-colored walls contrast with the dark furniture, while natural light enters from a nearby doorway.

Townhouse in Elizabethtown

4.98 out of 5 average rating, 276 reviews

Bear-BnB - Relaxing Bear Themed Space

You will be close to everything in Elizabethtown when you stay at this newly remodeled, centrally-located place with a Bear theme. Unique amenities unlike any experience Including: 1Gb Fiber with WiFi, 55" QLED TV, Nest Thermostat with Smoke & Carbon Monoxide, LoveSac Sactional with LoveSac SuperSac coined the ":Bear Chair", Keurig D-Duo Coffee, premium Therapeutic brand mattresses. Full Laundry, and Flywheel Exercise Bikes, Weber Natural Gas Grill and Outdoor Seating area. Included Laundry

4.95 out of 5 average rating, 132 reviews

A well-equipped kitchen area features modern appliances including a stove, oven, and microwave. A coffee maker is positioned on a wooden tray near a window, while bright cabinetry and smooth countertops create a clean, inviting space. Natural light illuminates the hardwood floor.

Camper/RV in Louisville

Stella Airstream at Progress Park in Derby City

The Stella is lovingly named after Airstream Founder Wally Byam's wife Stella! She is a 1983 Classic. This airstream is perfect for groups, families, or midweek getaways. Stella combines comfort, convenience, & a one of a kind outdoor experience. 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 bunkhouse. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

4.98 out of 5 average rating, 296 reviews

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

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.

4.99 out of 5 average rating, 242 reviews

A cozy living space features a brown sectional sofa adorned with a cushion displaying the phrase 'CALL ME OLD FASHIONED.' Green plants are positioned beside the couch, while patterned wall art and a decorative sign contribute to the inviting decor.

Home in Louisville

"Call Me Old-Fashioned"in Derby & Bourbon Country!

Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!

4.99 out of 5 average rating, 538 reviews

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!

Farm stay in Elizabethtown

4.99 out of 5 average rating, 145 reviews

Mini Cow Cottage! Peaceful Farm Getaway

Come enjoy this peaceful private getaway in a beautiful country setting that is still close to town and the bourbon trail. The cottage offers two bedrooms (one king, one queen) and one bath with an open floor plan, fully stocked kitchen, W/D, front and back covered porches, and don't forget the animals! We have mini Highland cattle, a horse, 3 very friendly barn cats, and spacious natural surroundings. There is also a walking trail along the woods, and a beautiful pond. Dogs welcome too!

4.96 out of 5 average rating, 160 reviews

The cottage is nestled among lush greenery, showcasing a unique design with corrugated metal and concrete. A wooden deck leads to the entrance, surrounded by neatly arranged flower beds. Windows provide ample natural light while blending harmoniously with the woodland surroundings.

Cottage in Coxs Creek

Bourbon Way Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS

4.98 out of 5 average rating, 240 reviews

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.

4.87 out of 5 average rating, 130 reviews

A comfortable living area is presented with a spacious grey sofa and an armchair positioned on a patterned rug. Natural light streams through the framed windows, and a stone fireplace serves as a focal point, complemented by a wall-mounted television.

Home in Louisville

Cute, Cozy, & Clean Home in Louisville

Welcome to this gem that is 20 minutes from Churchill Downs and Downtown Louisville. 15 minutes from the airport and Jim Beam! With parking galore, plenty of bedrooms, and a huge backyard, this is the ideal space for family and friends to reunite and connect. This is the perfect spot to stay to explore Louisville and surrounding areas - close enough to the excitement but far enough away to rest and relax! We would be happy to host you!

4.96 out of 5 average rating, 126 reviews

The exterior of a brick patio home is showcased, featuring a well-maintained landscape with shrubs lining the entrance. A one-car garage is visible, with a paved walkway leading to the front door. Trees are present in the background, and autumn leaves cover the ground.

Home in Shepherdsville

WynDown Spot

Wind down at this centrally located patio home that comes with an attached garage. This wine-themed home is open and airy, and has a screened-in patio for guests to enjoy. Located 0.2 miles from I-65 and minutes away from grocery stores and restaurants. Forest Edge Winery, James Beam Distillery, and MillaNova Winery are a 10-15 minute drive and many other attractions are nearby. You and your pets can "wine down" at Wyandot!

Popular amenities for Shepherdsville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 125 reviews

A well-lit pathway leads to an outdoor fire pit area surrounded by blue chairs. The scene features a wooden deck overlooking a wooded landscape, with a colorful sunset in the background, enhancing the peaceful atmosphere of the retreat.

Home in Mammoth Cave

Select June Dates Available! Sunsets + Stargazing

4.98 out of 5 average rating, 233 reviews

A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.

Cabin in Lawrenceburg

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

Superhost

A welcoming exterior view of a stylish house features a covered front porch with seating and decorative elements. The spacious interior showcases a cozy living area with comfortable seating and art on the walls. A well-maintained outdoor space includes a putting green. Natural light brightens the rooms.

Home in Jeffersonville

4.98 out of 5 average rating, 139 reviews

Walking Bridge, Putt Putt House

4.97 out of 5 average rating, 130 reviews

The log cabin is set on a hillside surrounded by trees, featuring a red metal roof and large windows. A wooden deck leads to the entry, providing views of the Ohio River and nearby farmland. The natural setting contributes to a peaceful ambiance.

Cabin in Leavenworth

BIG TIMBER RIVER CABINS, "The Hawk's Nest"

Home in Washington County

4.99 out of 5 average rating, 182 reviews

Bourbon Trail Summer POOL-ZONE! GameRm! Fish!

4.95 out of 5 average rating, 197 reviews

An outdoor fire pit area is surrounded by Adirondack chairs arranged in a circular pattern. Warm string lights hang overhead, illuminating the space, while the house stands in the background against a vibrant sunset sky.

Home in Pewee Valley

Bourbon Trail*Tesla EV charger* HOT TUB

4.94 out of 5 average rating, 111 reviews

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

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.

4.93 out of 5 average rating, 183 reviews

The Gathering Place

Family- and pet-friendly home rentals

4.86 out of 5 average rating, 195 reviews

A charming home is shown with a light-colored exterior, framed by dark shutters and manicured shrubs. A concrete path leads to the welcoming red front door. Lush greenery and flower beds enhance the outdoor space, complemented by a peaceful sky.

Home in Simpsonville

Charming 4 Bedroom classic home bourbon trail!

4.91 out of 5 average rating, 186 reviews

A spacious living area displays a mix of comfortable seating options, including a sofa, armchair, and patterned rug. A vibrant mural above the fireplace adds a pop of color. The adjoining kitchen is visible in the background, enhancing the open layout of the space.

Home in Shelby Park

Colonel Lou Lou's

4.93 out of 5 average rating, 1,197 reviews

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

4.91 out of 5 average rating, 324 reviews

The exterior of a charming single-story house is shown, featuring a covered porch and stone columns. Lush green bushes frame the entrance, and two seats are visible on the porch. A modest yard surrounds the house, with a clear sky above.

Home in Clifton Heights

Quiet Neighborhood Home With Outstanding Location

4.98 out of 5 average rating, 154 reviews

The cabin is elevated on stilts, surrounded by trees, and features a wraparound screened-in porch. A wooden deck leads to the entrance, where a flag hangs proudly. Gravel pathways converge near outdoor seating areas with picnic tables, providing a welcoming outdoor space.

Home in Elizabeth

Cabin on Lake Close to Louisville Ky

4.89 out of 5 average rating, 217 reviews

A single-story brick home is featured, surrounded by well-maintained landscaping. A paved driveway leads to a two-car garage, and a basketball hoop is positioned on the right. The yard offers a grassy area with neatly trimmed bushes and trees providing light shade.

Home in Louisville

Lilly's Pad

4.93 out of 5 average rating, 288 reviews

An open living space features a wall-mounted TV opposite a sectional sofa. A bar-height dining table with seating for four is positioned beside the sofa. Light walls and large windows contribute to a bright atmosphere, while decorative wall art adds visual interest.

Home in Iroquois

Parkside Pad - Iroquois Park

4.89 out of 5 average rating, 179 reviews

An open-concept apartment features a kitchen island with seating for four, surrounded by bright yellow walls. Natural light highlights the living area, where comfortable seating is arranged. Decorative elements, including framed artwork and potted plants, enhance the inviting atmosphere.

Farm stay in Raywick

Adorable studio with fireplace. Bourbon trail

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 155 reviews

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

4.91 out of 5 average rating, 143 reviews

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

Apartment in Central Business District

A modern living area features a light gray sofa adorned with decorative pillows and a plaid throw blanket. Two red armchairs complement the space, which is anchored by a dark coffee table. A colorful piece of wall art and large windows allow natural light to fill the room.

4.97 out of 5 average rating, 184 reviews

King Suite | Golf Sim · Pool · Hot Tub · Parking

5 out of 5 average rating, 125 reviews

An outdoor seating area is displayed, featuring two white armchairs and a stone-top coffee table, arranged on a green and white striped rug. String lights illuminate the space, which is bordered by tall green shrubs and a wooden fence.

Home in Prospect

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

4.94 out of 5 average rating, 236 reviews

The exterior of a spacious carriage house is shown, featuring a stone facade and a grey roof. Three garage doors are visible, along with multiple windows framed in green shutters. A large tree provides shade to the front porch, which invites a sense of coming home.

Cottage in Shelbyville

Cozy Cottage on Firefly Farm

4.95 out of 5 average rating, 215 reviews

Luxury Retreat with Hot Tub

Superhost

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.

4.83 out of 5 average rating, 120 reviews

Lake Livin' & Bourbon Sippin'