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! 🥃✨

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!

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, 264 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.

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, 260 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!

4.99 out of 5 average rating, 594 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!

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!

4.98 out of 5 average rating, 264 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.

4.97 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.

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.

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.

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

4.91 out of 5 average rating, 150 reviews

Superhost

The exterior of a single-story home is shown, featuring a wooden porch with a railing. The brick facade is complemented by a grassy area and trees in the background. A concrete walkway leads to the entrance, enhancing accessibility.

Home in Elizabethtown

Kentucky Comfort House

3 bedrooms one bath 1,100 sf nice covered decks to sit out and enjoy yourself. 6 miles to sports park 7 to Bluegrass sports facility. Close to shopping and mall. Beautiful place to take a break. 3 bed’s California king, queen, twin xl.

4.8 out of 5 average rating, 142 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

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

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

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!

4.88 out of 5 average rating, 182 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

4.99 out of 5 average rating, 122 reviews

Home in Springfield

Bourbon + HotTub + FirePit "Fall Magic"

4.98 out of 5 average rating, 120 reviews

The game room features a poker table surrounded by comfortable chairs, accented by modern lighting. An outdoor hot tub is enclosed by a wooden deck, inviting relaxation. A fire pit area with several Adirondack chairs presents a cozy gathering spot. A billiards table is positioned under stylish light fixtures.

Home in Bardstown

Bourbon Basecamp: 1.5 Acres, Game + Movie Room 3BR

4.91 out of 5 average rating, 108 reviews

An outdoor space features a large swim spa hot tub beside a wooden bar with four stools. A gazebo is adorned with seating for relaxation. A stone pathway leads towards the backyard, with a manicured lawn and trees bordering the property.

Home in Clarksville

10 min to Lou~Huge Hot Tub~Fenced Backyard~Games

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 106 reviews

Home in Elizabethtown

Old Maple House - 1901 charmer on Bourbon Trail

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, 226 reviews

Lilly's Pad

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

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

4.87 out of 5 average rating, 109 reviews

4.98 out of 5 average rating, 167 reviews

Home in Elizabeth

Cabin in the Woods on Lake Close to Louisville Ky

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 .

4.94 out of 5 average rating, 202 reviews

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

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.

4.94 out of 5 average rating, 332 reviews

Parkside Pad - Iroquois Park

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

5.0 out of 5 average rating, 131 reviews

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

Home in Washington County

Bourbon Trail Pool&Game Zone! Keeneland! 3 acres!

4.99 out of 5 average rating, 192 reviews

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!

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!

4.84 out of 5 average rating, 129 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'

Apartment in Central Business District

A spacious living area is depicted, featuring a comfortable gray sofa with decorative pillows positioned next to a side table. A modern kitchen with sleek cabinetry and stainless steel appliances is visible in the background. Large windows allow for ample natural light, illuminating the wood-style flooring.

4th Street Suites - Opulent King Bed Suite

4.9 out of 5 average rating, 338 reviews