Family-friendly vacation rentals in Shepherdsville

4.98 out of 5 average rating, 125 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! 🥃✨

KitchenFamilyHiking

4.99 out of 5 average rating, 107 reviews

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!

FamilyIndoor spacesHospitality

A modern kitchen space features white cabinetry and open shelving, displaying neatly arranged dishes and plants. A breakfast bar with four metal stools offers a casual dining area, complemented by a window that allows natural light to brighten the room.

4.97 out of 5 average rating, 263 reviews

502 House @ Progress Park w/ Game Room

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The 502 house 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. Show up, settle in, and start relaxing. 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.

FamilyKitchenCheckout

4.99 out of 5 average rating, 593 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!

Indoor spacesKitchenCondition

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.

4.99 out of 5 average rating, 259 reviews

"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!

Indoor spacesFamilyLocation

5.0 out of 5 average rating, 102 reviews

A spacious living area features a comfortable brown sofa and a wooden coffee table, complemented by a ceiling fan. A dining set occupies one corner, while equestrian-themed artwork adorns the walls. Natural light enters through sliding glass doors, enhancing the overall ambience.

Home in Radcliff

Cozy, 3 bedroom home 4 miles from Fort Knox

Discover a cozy home just 4 miles from Fort Knox, offering a personal driveway and high-speed fiber Wi-Fi. With three comfortable bedrooms accommodating up to 6 guests, including a queen, a twin trundle, and two full-size beds. Plus, you're conveniently situated 4.6 miles from the Patton Museum and 4.4 miles from the Chaffee gate/Visitor Center. Experience comfort, convenience, and proximity to local attractions. Your perfect Fort Knox getaway awaits!

Indoor spacesKitchenAccuracy

4.98 out of 5 average rating, 263 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.

FamilyKitchenWalkability

4.95 out of 5 average rating, 104 reviews

A spacious green yard is visible, bordered by trees. A circular driveway leads to a single-story house with a covered front porch. Surrounding grass is neatly mowed, offering ample space for outdoor activities.

Home in Elizabethtown

Secluded country getaway

Bring the whole family to this great place with lots of room for fun.There is a large yard for the kids to play. It has an upstairs exercise room over the garage.A large back porch for grilling or relaxing.There is a wood fire pit plus a gas one too. Plenty of room inside.Easily sleeps 10. It is located close to the interstate and E-town Sports park. A large yard for outside activities. It is quiet and peaceful located on 6 .5 acres.

FamilyKitchenLocation

4.97 out of 5 average rating, 111 reviews

The front of the home features a welcoming porch area with two chairs placed beside a small table. Lush green grass and decorative plants frame the porch, which is complemented by a large shade tree. The entrance is marked by a wooden door with clear glass panels.

Home in Elizabethtown

The North Mantle House

THIS IS THE ONE! Welcome to The North Mantle! Less than 1.2 MILES from downtown Elizabethtown! 3 MILES to Bluegrass Sportsplex and ONLY 7 MILES to Ford BlueOval Battery Park. Centrally located w/plenty of parking! Our completely renovated place accommodates up to 8 guests comfortably! Open floor plan offers 3 bedrooms & 2 full bathrooms. The fully equipped kitchen has an island with seating for 2 and a dining table with seating for 8.

Indoor spacesFamilyCleanliness

Superhost

Home in Shepherdsville

Cedar Forest House

Enjoy the location convenience this quaint home has to offer. The Cedar Forest house is a 3 bedroom home located 0.2 miles from the I-65 exit and a short distance to many nearby attractions including bourbon distilleries, wineries, and Bernheim Forest. During your stay, guests can enjoy the two sitting rooms, each with their own smart TV, and stocked with board games. Pets are welcome for an additional pet fee.

FamilyKitchenDecor

4.88 out of 5 average rating, 101 reviews

4.97 out of 5 average rating, 381 reviews

A cozy cabin is framed by lush greenery, featuring a wrap-around porch with decorative lights. Large windows offer an inviting glimpse into the interior, while a wooden exterior blends harmoniously with the natural surroundings. A spacious lawn enhances the serene atmosphere of the property.

Cabin in Hardin County

Cabin at Calico Springs

Welcome to The Cabin at Calico Springs, located on 150 acres with nine natural springs, a stream that runs year round, hiking trails, and beautiful forests. This cozy cabin features a great room with living, dining, and kitchen space. There is a private bathroom. The loft has a queen, a bunk bed (2 twins) and a twin. The downstairs has a wrap around porch with room for dining, swinging, and relaxing.

Indoor spacesFamilyWalkability

Apartment in Shepherdsville

A spacious living area features a mix of seating options, including a black leather sofa and a brown couch, centered around a coffee table. Wall art and memorabilia adorn the light-colored walls, and a ceiling fan provides airflow in the bright room.

Blast from the Past

This unit has a very spacious layout. It has all type of memorabilia from the past which will bring back all types of memories. It has 1 king and 2 queen beds with a roll out bed in the closet for that extra quest. This is one half of a duplex. It has plenty of parking and is located on our Venue property. Check out our guide book for local attractions and mileage

KitchenFamilyGetting around

4.91 out of 5 average rating, 148 reviews

Popular amenities for Shepherdsville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 110 reviews

Cabin in Bardstown

Cabin*Hot-Tub*Pickleball*Speakeasy* Bourbon Trail

Indoor spacesFamilyView

A jacuzzi hot tub is illuminated by blue lights, creating a serene ambiance. The steam gently rises from the surface of the water, suggesting warmth and relaxation. Surrounding the tub, wooden decking and softly glowing lights add to the inviting atmosphere.

4.89 out of 5 average rating, 159 reviews

Parkside Retreat

FamilyIndoor spacesGetting around

4.85 out of 5 average rating, 104 reviews

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

FamilyIndoor spacesAccuracy

4.95 out of 5 average rating, 137 reviews

A spacious deck is highlighted by several green Adirondack chairs and a picnic table beneath a wooden pergola with string lights. A hot tub is visible nearby, with a natural setting of trees in the background and a colorful sky at dusk.

Cottage in Hudson

Hot Tub, Large game area, book fall dates today!

Indoor spacesFamilyCondition

4.88 out of 5 average rating, 181 reviews

A covered outdoor space features a hot tub and comfortable seating arrangements. Styled with a patterned rug, the area is enhanced by string lights overhead. A secure wooden fence surrounds the backyard, ensuring privacy and safety for guests.

Home in Jeffersonville

Best of the Ville’s Modernised

FamilyKitchenOutdoor spaces

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.

4.92 out of 5 average rating, 298 reviews

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

KitchenFamilyQuiet

4.99 out of 5 average rating, 120 reviews

Home in Springfield

Fall Bourbon Escape | Hot Tub + Fire Pit

Indoor spacesKitchenOutdoor spaces

Home in Washington County

#1 Bourbon Trail POOL&GAME ZONE! Keenland! Hottub!

FamilyKitchenPets

4.99 out of 5 average rating, 191 reviews

Family- and pet-friendly home rentals

Superhost

A cozy studio room features a spacious bed with dark linens, situated beside large windows with dark drapes. A compact dining table and chairs are positioned near a kitchenette and a gray couch adds additional seating. A refrigerator is also visible in the background.

Guest suite in Louisville

Cute and Cozy Private Studio Getaway in Louisville

KitchenFamilyAir conditioning

4.82 out of 5 average rating, 203 reviews

4.96 out of 5 average rating, 105 reviews

Home in Elizabethtown

Old Maple House - 1901 charmer on Bourbon Trail

KitchenIndoor spacesNearby

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.

4.89 out of 5 average rating, 225 reviews

Lilly's Pad

KitchenIndoor spacesGrill

4.99 out of 5 average rating, 114 reviews

A country farmhouse is set on a gentle hill, surrounded by lush green grass and trees. The building features a light-colored exterior, a front porch, and a staircase leading to the entrance. The clear blue sky enhances the peaceful rural setting.

Farm stay in Loretto

Knobview. Peaceful 3 BR Farm House on Bourbon Trl.

KitchenIndoor spacesLocation

4.98 out of 5 average rating, 165 reviews

Home in Elizabeth

Cabin in the Woods on Lake Close to Louisville Ky

KitchenIndoor spacesGetting around

4.92 out of 5 average rating, 1255 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

KitchenIndoor spacesHospitality

Guest suite in Brandenburg

A two-story house is shown from the driveway, featuring a covered front porch with white railings. The front yard is grassy, and an American flag flies on a pole. A paved driveway leads to a two-car garage, with two vehicles visible inside.

Private Basement on 7 Acres in the Country

KitchenIndoor spacesPool

4.87 out of 5 average rating, 109 reviews

4.97 out of 5 average rating, 152 reviews

An aerial view captures the property surrounded by lush farmland. The layout includes a swimming pool and neighboring structures, featuring manicured lawns and ample greenery. A winding driveway leads through the landscape, emphasizing the spaciousness of the 72-acre setting.

Farm stay in Raywick

Missy’s unique stays on the bourbon trail .

KitchenIndoor spacesPool

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 164 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

FamilyKitchenValue

4.95 out of 5 average rating, 114 reviews

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 spacesKitchenCondition

4.91 out of 5 average rating, 148 reviews

Cottage in Taylorsville

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

FamilyKitchenTV

4.84 out of 5 average rating, 128 reviews

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'

FamilyIndoor spacesLayout

4.95 out of 5 average rating, 212 reviews

A comfortable living room showcases a mix of upholstered furniture, including a plaid sofa and recliners. Natural light enters through the dressed windows, highlighting wooden floors. A coffee table rests in the center, and decorative lamps provide ambient lighting.

Home in Lebanon

Downtown Abode Your home away from home.

FamilyIndoor spacesWalkability

4.89 out of 5 average rating, 137 reviews

Home in Taylorsville

#18 Kentucky Sunrise - Lakefront Home with spacuio

FamilyKitchenQuiet

4.99 out of 5 average rating, 155 reviews

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 spacesFamilyBackyard