Family-friendly holiday rentals in Jeffersontown

4.96 out of 5 average rating, 112 reviews

A spacious living area is furnished with a dark sectional couch and two wooden coffee tables. A dining table with four chairs is positioned nearby. The room features light wood flooring and is complemented by a window and an air conditioning unit.

Guesthouse in Louisville

Breakfast At Tiffany's

This private detached in-law suite with driveway access will make you feel like your staying with family. An open plan living area let's you relax and feel at home while enjoying a modern kitchen, spacious shower, and cozy bedroom with a vaulted ceiling and exposed brick. We're located within walking distance of Charlie Vettiner Golf Course and Park so if you have an early tee time, a long game, or come into town for a Pickle Ball tournament, you're welcome to stay with family in our suite.

Indoor spacesKitchenAccuracy

Guest suite in Louisville

A colorful living area is furnished with a patterned sectional sofa and a round glass coffee table. Natural light enters through multiple windows, illuminating the artful wall decor. A kitchenette area with modern appliances is visible in the background, enhancing the space's functionality.

4.95 out of 5 average rating, 320 reviews

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

FamilyIndoor spacesAmenities

4.98 out of 5 average rating, 299 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.

Indoor spacesKitchenQuiet

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, 244 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 spacesGetting around

4.99 out of 5 average rating, 547 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!

KitchenFamilySleep quality

5 out of 5 average rating, 257 reviews

An updated kitchen features stainless steel appliances, including a fridge and microwave, complemented by white cabinetry. A central island with metal stools provides additional workspace. A wooden cabinet displays dishware, and decorative plates are mounted on the wall, enhancing the room's functional design.

Home in Middletown

Perfect for Work or Play, Close to Everything!

Whether you're here for work or play, our Airbnb offers the perfect base for your Kentucky adventures! Welcome to your home away from home! Nestled in the quiet suburbs, our modern & spacious retreat offers the perfect blend of comfort & convenience. Whether you’re here to explore the famous Bourbon Trail, work remotely, or simply unwind, you’ll find everything you need right here! Close to shopping, dining, entertainment, major highways, top bourbon distilleries and downtown Louisville.

FamilyIndoor spacesAmenities

A spacious living area features a comfortable gray sofa adorned with decorative cushions, positioned next to large windows offering expansive water views. A glass coffee table rests on tiled flooring, surrounded by light-colored decor accents. Natural light fills the space, enhancing the serene atmosphere.

4.96 out of 5 average rating, 178 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

FamilyKitchenParking

A cozy living room is presented with a dark sofa facing a white-brick fireplace. Above the fireplace, a flat-screen television is mounted. Two armchairs flank the fireplace, while a small ottoman completes the seating arrangement. Light-colored drapes frame the windows, and artwork decorates the walls.

4.87 out of 5 average rating, 236 reviews

Private EAST END gem, minutes to everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

FamilyIndoor spacesHospitality

4.91 out of 5 average rating, 145 reviews

Home in Jeffersontown

Spacious Louisville getaway with private backyard!

Welcome to your Louisville retreat, designed with large groups in mind. Set in a quiet, residential neighborhood, this spacious home offers a calm, serene atmosphere ideal for unwinding together. With 5 comfortable bedrooms and multiple living areas, it easily accommodates up to 16 guests. Enjoy a fully equipped kitchen, a cozy fireplace, and a private backyard perfect for relaxed mornings and peaceful evenings—ideal for families and group getaways seeking comfort and quiet.

FamilyIndoor spacesDecor

Guest suite in Louisville

The inviting bedroom features a spacious bed with white linens and a soft green throw. A mounted projector is positioned on the ceiling, with greenery-patterned wallpaper creating a serene ambiance. Two bedside tables with lamps and a bench at the foot of the bed enhance functionality.

4.99 out of 5 average rating, 227 reviews

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

Indoor spacesKitchenWalkability

4.92 out of 5 average rating, 168 reviews

The exterior of the home features a light beige facade with a metal roof and a vibrant red front door. Two shrubs frame the entrance, and the porch is accessed by three steps, providing a welcoming approach. Clear skies and lush greenery enhance the setting.

Home in Middletown

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

FamilyKitchenAccuracy

Campervan/RV in Louisville

The interior of the Airstream showcases a modern layout with a cozy dining area featuring a dark table and beige seating. A spacious bed is visible in the background, complemented by neutral tones and warm lighting. Large windows allow natural light to fill the space.

5 out of 5 average rating, 154 reviews

The GiGi Airstream, Lakeside at Progress Park

This Gigi is a 2022 Airstream Flying Cloud w/ all the bells and whistles. Everything you need is already here. Perfect for groups, families, or midweek getaways. 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 bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

Indoor spacesFamilyOutdoor spaces

Popular amenities for Jeffersontown family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.91 out of 5 average rating, 144 reviews

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

KitchenFamilyAccess

4.98 out of 5 average rating, 145 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

KitchenIndoor spacesCheck-in

5 out of 5 average rating, 262 reviews

The exterior of Deerview Cabin features a wooden porch with a welcome sign, surrounded by hanging plants and potted greenery. A rustic metal roof contrasts with the natural wood siding. Chairs are placed on the porch, inviting relaxation in a serene rural setting.

Home in La Grange

Romantic country getaway with hot tub

FamilyKitchenLong stay

4.97 out of 5 average rating, 134 reviews

A relaxing outdoor seating area features a framed gas fire pit at the center, surrounded by plush seating. Scenic water views are complemented by string lights and the warm hues of sunset, creating a tranquil atmosphere for evening gatherings.

Home in Jeffersonville

Upscale Waterfront w/Sauna Cinema HotTub Pet Views

FamilyIndoor spacesDecor

4.95 out of 5 average rating, 199 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

KitchenFamilyHiking

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

KitchenIndoor spacesCheckout

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.

4.94 out of 5 average rating, 186 reviews

The Gathering Place

FamilyIndoor spacesSleep quality

The cottage features a two-story structure with a light gray exterior and a welcoming entrance. A front staircase leads to a covered porch area, framed by well-maintained shrubs and greenery. Large windows provide natural light to the inviting living spaces within.

4.89 out of 5 average rating, 149 reviews

Lake Refuge near Louisville & Bourbon Trail #52

Indoor spacesKitchenLaundry

Family- and pet-friendly home rentals

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.

4.92 out of 5 average rating, 198 reviews

Colonel Lou Lou's

FamilyIndoor spacesBackyard

A light-filled living space showcases a comfortable grey couch adorned with colorful cushions. A wooden coffee table with decorative bowls sits in front, while an open kitchen area is visible in the background, featuring modern appliances and bright cabinetry.

4.9 out of 5 average rating, 120 reviews

2BR Home Near Zoo & Fairgrounds – Family-Friendly!

FamilyIndoor spacesCondition

A cozy living area features a gray sofa adorned with blue cushions and a decorative throw pillow. A light-colored armchair with a floral pattern complements a round coffee table, while a plant and lamp are positioned on a side table. Natural light enters through the windows.

4.83 out of 5 average rating, 165 reviews

Sugar Maple Corner: 5min to KY Expo Center and Zoo

FamilyKitchenGetting around

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.

4.91 out of 5 average rating, 328 reviews

Quiet Neighborhood Home With Outstanding Location

KitchenIndoor spacesOutdoor spaces

4.94 out of 5 average rating, 737 reviews

A bright living area features a coral-colored sofa adorned with patterned cushions. Two wooden side tables flank the sofa, with lamps providing soft lighting. A television sits on a wooden cabinet across from a gray armchair, while a decorative rug adds warmth to the hardwood floor.

Apartment in Louisville

Charming Highlands apartment

FamilyIndoor spacesCleanliness

4.88 out of 5 average rating, 224 reviews

A wooden sign is displayed on a wall, featuring the text 'Welcome to Our Nest' in an elegant cursive font. The sign has a rustic design with a whitewashed finish, and a pink ribbon is tied at the top for hanging.

Loft in Crestwood

Welcome to the Nest!

KitchenFamilyLaundry

4.95 out of 5 average rating, 781 reviews

A front porch is featured, constructed of wood, with a round table set for four. Decorative flowers are arranged in a vase at the center. Sunlight filters through the open roof, illuminating the surrounding greenery visible beyond the railing.

Farm stay in La Grange

The Cottage at StoneLedge 2 bedroom/1bath

FamilyKitchenCondition

Apartment in East Market District

A cozy living area is highlighted by a collection of framed artworks and wall decor, reflecting a mix of styles. A gray sofa sits in front of a vibrant red door, while a person stands on a ladder, adjusting the arrangement of the art pieces.

4.97 out of 5 average rating, 251 reviews

Historic Braden Suite in heart of NuLu action

KitchenIndoor spacesCheck-in

Family-friendly home rentals with a pool

Guest suite in Louisville

A heated saltwater swimming pool is surrounded by a concrete patio and lush greenery. The area features a spacious cabana with seating, a chaise lounge, and colorful pool floats. Nearby, a small garden and manicured lawn enhance the outdoor setting.

4.96 out of 5 average rating, 397 reviews

Cherokee Park Oasis with Pool and Hot Tub

FamilyKitchenValue

A split-level home is displayed, featuring a combination of brick and siding. A well-maintained garden with vibrant flowers lines the front. A mature tree provides shade, and the house is accented with dark shutters beside the windows. A welcoming sign is visible in the yard.

4.94 out of 5 average rating, 31 reviews

The Getaway!

FamilyKitchenPool

4.96 out of 5 average rating, 158 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

FamilyIndoor spacesCondition

5 out of 5 average rating, 127 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

Indoor spacesKitchenCondition

4.94 out of 5 average rating, 237 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

KitchenIndoor spacesWi-Fi

4.98 out of 5 average rating, 59 reviews

A colorful living area features a striking red ceiling and vibrant wall art depicting a circus theme. Seating includes a gray sofa, a round dining table, and unique patterned chairs. Large windows allow natural light to fill the space, enhancing the playful decor.

Home in Prospect

CIRCO LOCO - uNCommon Stay

KitchenIndoor spacesAccess

4.95 out of 5 average rating, 218 reviews

Luxury Retreat with Hot Tub

FamilyIndoor spacesPool