Family-friendly vacation rentals in Shepherdsville

4.98 out of 5 average rating, 123 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 spacesKitchenAccuracy

4.96 out of 5 average rating, 114 reviews

A modern cabin features a large deck surrounded by lush greenery, showcasing expansive glass windows that provide ample natural light. The structure has a sloped roof and is partially nestled among tall trees, highlighting the serene forest setting.

Cabin in New Pekin

Anjuna House - a Scandi riverfront forest getaway

Welcome to the enchanting retreat of "Anjuna," nestled among a sprawling forest in the heart of southern Indiana. This modern 4-bedroom, 3 bathroom luxury cabin features 14' floor-to-ceiling windows, and 1000+ sqft deck! Outside there are 12 acres of forest to explore, an outdoor shower and a tranquil river which meanders through the property. Anjuna is near Knobstone trail, Marengo Cave, and the bourbon trail in Louisville. Bring family, friends or just yourself to relax or explore at Anjuna!

KitchenIndoor spacesWifi

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, 257 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!

KitchenIndoor spacesBackyard

4.99 out of 5 average rating, 589 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!

KitchenIndoor spacesAir conditioning

The exterior view of the red-themed house is shown, emphasizing the sloped roof and welcoming front porch. A spacious deck features seating options and a grill. Lush greenery surrounds the area, contributing to a peaceful outdoor environment.

4.99 out of 5 average rating, 124 reviews

Colonial Hideout | Close to fairgrounds!

Ready for a relaxing stay in Louisville, Kentucky?! Welcome to a wonderfully homey stay minutes away from the KY Expo Center & Kentucky Fair Grounds. Perfect for hitting the Kentucky Bourbon Trail, heading to one of Louisville's many events, or heading to a game at the KFC Yum! Center. The property & driveway can easily manage horse trailers and car trailers if you’ve got a lot to haul. We look forward to hosting you! Family Ready: Pack n Play, High Chair, Plastic Plates & Cups

KitchenIndoor spacesGrill

4.98 out of 5 average rating, 164 reviews

Home in Elizabeth

Cabin in the Woods on Lake Close to Louisville Ky

Escape to Little Cedar Lodge, a secluded lakefront cabin just 20 minutes from downtown Louisville. Enjoy beautiful lake views from the huge screened porch, a guest favorite for relaxing among the trees and watching abundant wildlife. This warm, wood-filled A-frame sleeps up to 10 with 2 queen bedrooms plus a spacious loft. Enjoy 2 full baths, a fully stocked kitchen, open living area, fireplace (electric) and plenty of parking. Peaceful, private and close to everything!

KitchenFamilyComfort

Guest suite in Shepherdsville

The outdoor space features a concrete patio surrounded by colorful trees, showcasing a blend of autumn hues. A charcoal and gas grill is covered, positioned on one side of the patio. The entrance door to the lower-level unit is visible, offering a private and secure access point.

4.99 out of 5 average rating, 101 reviews

Private 1000 sq ft 1-bedroom lower level apartment

Relax in this beautiful wooded setting in Bourbon Country less than 4 miles from I-65. Private entrance into freshly painted 1-bedroom unit with new kitchen and 9' ceilings. Perfectly located near 19 Bourbon Distilleries, 4 Wineries, Bernheim Forest, Knob Creek Gun Range, Churchill Downs and other exciting destinations. Jim Beam Distillery & Forest Edge Winery are 7 min away. There is a seasonal (shared) concrete patio, deck and pool available in the warmer months.

KitchenIndoor spacesTV

Place to stay in Shepherdsville

A spacious sleeping area features a king bed with a soft beige quilt and matching pillows. Two bedside lamps provide warm lighting beside wooden nightstands. The ceiling is accented by textured panels, and the cozy carpet extends across the floor.

4.89 out of 5 average rating, 347 reviews

A Little Bit of Kentucky

A unique loft apartment near Louisville, Bardstown and just across the river from Indiana. This is attached to our Wedding venue for the convenience of anyone who is coming in for a wedding. It has its on separate entrance away from the venue so you wont be bothered by anyone. We are more than willing to accommodate you in any way we can. Let us know what you need and we will do our best to meet your needs. Check our guide book for local attractions and mileage

Indoor spacesKitchenCondition

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 spacesKitchenValue

4.98 out of 5 average rating, 260 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.

FamilyIndoor spacesAir conditioning

4.93 out of 5 average rating, 107 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.

FamilyKitchenComfort

Superhost

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, 142 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!

Indoor spacesKitchenOutdoor spaces

Popular amenities for Shepherdsville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.84 out of 5 average rating, 103 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

KitchenFamilyHospitality

4.98 out of 5 average rating, 157 reviews

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

Walking Bridge, Putt Putt House

FamilyIndoor spacesLocation

4.9 out of 5 average rating, 125 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

Indoor spacesKitchenLayout

4.93 out of 5 average rating, 106 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

KitchenIndoor spacesTV

4.94 out of 5 average rating, 112 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

KitchenFamilyWifi

4.96 out of 5 average rating, 128 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 spacesBackyard

Superhost

A stylish corner of the room features a unique black bench against a textured green wall, contributing modern design elements. A small black side table holds decorative items, while a patterned throw pillow rests on the bench. The space is illuminated by natural light from nearby windows.

Home in New Albany

4.88 out of 5 average rating, 188 reviews

GreenHouse New Albany

FamilyKitchenPets

A charming two-story gingerbread home features a red brick facade and a distinctive gabled roof. The exterior includes front steps leading to the main entrance and a porch area with seating. Lush greenery and a neatly maintained lawn are present, adding to the home's welcoming appearance.

4.88 out of 5 average rating, 262 reviews

Why Not Stay in Louisville? (up to 9 guests)

FamilyIndoor spacesLocation

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 1247 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

Indoor spacesFamilyBreakfast

4.94 out of 5 average rating, 200 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

KitchenFamilyAccess

4.84 out of 5 average rating, 206 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

Indoor spacesKitchenCheck-in

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.

4.87 out of 5 average rating, 109 reviews

Private Basement on 7 Acres in the Country

FamilyKitchenSleep quality

4.91 out of 5 average rating, 114 reviews

A dining area is illuminated by a unique light fixture hanging from a high ceiling. A round table set for dining is surrounded by wooden chairs. Stairs lead to an upper level, and windows allow natural light to enhance the space.

Bungalow in West Point

Historic river town, hiking, biking trails.

KitchenFamilyLaundry

The kitchen features a warm wood countertop complemented by white cabinets and shelves. A stainless steel sink and dishwasher are visible, along with a Keurig coffee maker. Natural light filters through the window, illuminating neatly arranged dishes and kitchen supplies.

4.98 out of 5 average rating, 179 reviews

Two Bedrooms walking to Expo Center & KY Kingdom!

KitchenIndoor spacesDecor

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, 326 reviews

Parkside Pad - Iroquois Park

FamilyIndoor spacesLocation

4.97 out of 5 average rating, 140 reviews

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

Indoor spacesKitchenHospitality

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 113 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!

KitchenFamilyAccess

Home in Washington County

4.99 out of 5 average rating, 191 reviews

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

KitchenFamilyValue

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

Indoor spacesFamilyAmenities

4.94 out of 5 average rating, 189 reviews

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.

Cottage in Taylorsville

The Gathering Place

FamilyIndoor spacesAir conditioning

4.95 out of 5 average rating, 223 reviews

Cottage in Taylorsville

Luxury Retreat with Hot Tub

FamilyKitchenGrill

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.

4.9 out of 5 average rating, 331 reviews

4th Street Suites - Opulent King Bed Suite

Indoor spacesKitchenLayout

5.0 out of 5 average rating, 130 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

Indoor spacesKitchenParks