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! 🥃✨

Indoor spacesFamilyAccess

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.

Indoor spacesKitchenView

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 spacesFamilyAccess

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!

FamilyIndoor spacesCheck-in

A bright living room features a dark tufted sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, and a large flat-screen TV is mounted above a white mantel. Two armchairs are positioned near a window, with natural light flowing into the space.

4.94 out of 5 average rating, 463 reviews

DOWNTOWN LOUISVILLE ⭐ Expo Center⭐ 3 BR, 2 BT

- 3 min drive to U of Louisville - 5 min drive to KY Expo Center - 7 min drive to Louisville Zoo This gorgeous 3-bed, 2-bath house is less than 4 miles from downtown Louisville. With its fully-equipped kitchen, spacious rooms & completely renovated kitchen, the house is the perfect base for large groups wanting to explore the city. Enjoy the wide variety of shops, restaurants, & bars nearby. Kentucky Derby fans love the close proximity to Churchill Downs. No Locals Please

FamilyIndoor spacesCheckout

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!

KitchenFamilyCheckout

4.91 out of 5 average rating, 373 reviews

The cabin exterior is constructed with natural wood logs, featuring a metal roof in a deep hue. Windows allow natural light to enter, with a covered porch area to the side. A paved driveway leads to the entrance, surrounded by natural greenery.

Cabin in Elizabethtown

The Cabin- private,cozy, firepit, hammock, pacman

Take a break and unwind at this peaceful oasis. Blurring the lines between structure and nature, this cabin retreat inspires a feeling of tranquility. The footprint compacts everything one could need- living, kitchen, bed, bathroom, washer/dryer, games and more. Enjoy the peaceful sounds of nature while napping in the hammock. Cook dinner over an open flame in the firepit. Test your skills to beat the high score on PacMan arcade or the foosball table.

Indoor spacesFamilyAccess

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.

KitchenFamilyWifi

4.93 out of 5 average rating, 110 reviews

Cabin in Bardstown

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

Welcome to your secluded sanctuary nestled within 10 acres of pristine land. Entering the cabin, you're enveloped in warmth and coziness. The interior is adorned with knotty pine walls, lending a rustic charm to the space. As the sun sets, casting a golden glow over the landscape, you gather around the fire pit with friends and family. Your cabin is a sanctuary where time stands still, and the beauty of nature surrounds you at every turn.

Indoor spacesFamilyAir conditioning

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.

4.85 out of 5 average rating, 144 reviews

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!

KitchenIndoor spacesDecor

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.

FamilyKitchenCondition

4.88 out of 5 average rating, 101 reviews

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.

KitchenFamilyGetting around

Popular amenities for Shepherdsville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 126 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

KitchenFamilyHot tub

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

Indoor spacesFamilyBathroom

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

KitchenIndoor spacesBiking

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

FamilyKitchenAir conditioning

A backyard is displayed, featuring a hot tub and a gas fire pit surrounded by four outdoor chairs. Patio heaters provide warmth, and the space is framed by a fence. The modern home is visible in the background, illuminated by evening light.

4.95 out of 5 average rating, 313 reviews

Hot Tub | Fenced-in Yard | King Bed | Walk to Nulu

KitchenFamilyQuiet

4.96 out of 5 average rating, 130 reviews

The image collage features various spaces of a stylish home. A cozy lounge area with a fireplace is shown, alongside an outdoor hot tub surrounded by greenery. The dining area is connected to a deck, and a game room with a bar creates an inviting entertainment space.

Home in Bardstown

StillHill: HotTub GameRoom Whiskey Lounge Acreage

FamilyIndoor spacesCheck-in

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

KitchenFamilyBathroom

Home in Washington County

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

KitchenFamilyPets

4.99 out of 5 average rating, 191 reviews

Family- and pet-friendly home rentals

Guest suite in Louisville

A cozy efficiency room features a spacious bed covered in patterned bedding and a comfortable couch. A mirror and decorative artwork adorn the walls, with bedside tables and soft lighting from lamps. The en-suite bathroom is partially visible in the background.

One Room Apartment with Private Off Street Parking

FamilyKitchenLong stay

4.96 out of 5 average rating, 185 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.

4.89 out of 5 average rating, 225 reviews

Lilly's Pad

KitchenIndoor spacesCheckout

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.

KitchenFamilyQuiet

Guest suite in Louisville

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.

Cute and Cozy Private Studio Getaway in Louisville

Indoor spacesFamilyCheck-in

4.82 out of 5 average rating, 203 reviews

4.84 out of 5 average rating, 209 reviews

A cozy bedroom features a spacious bed layered with decorative pillows and a patterned throw. Soft lighting is provided by bedside lamps, while a small bench sits at the foot of the bed. Natural light filters through sheer drapes over a window.

Home in Elizabethtown

The Nantucket Suites

KitchenFamilyQuiet

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

KitchenFamilyHospitality

4.87 out of 5 average rating, 109 reviews

4.98 out of 5 average rating, 165 reviews

Home in Elizabeth

Cabin in the Woods on Lake Close to Louisville Ky

Indoor spacesKitchenTV

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, 331 reviews

Parkside Pad - Iroquois Park

FamilyIndoor spacesAir conditioning

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 148 reviews

Cottage in Taylorsville

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

Indoor spacesKitchenView

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

KitchenIndoor spacesQuiet

4.91 out of 5 average rating, 107 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

Indoor spacesKitchenComfort

4.89 out of 5 average rating, 137 reviews

Home in Taylorsville

#18 Kentucky Sunrise - Lakefront Home with spacuio

KitchenFamilyRiver

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!

FamilyKitchenHospitality

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'

KitchenFamilyOutdoor spaces

4.99 out of 5 average rating, 154 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!

FamilyKitchenPool