Family-friendly holiday rentals in Middletown

4.95 out of 5 average rating, 121 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.

KitchenIndoor spacesAmenities

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, 326 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.

KitchenIndoor spacesHeating

4.98 out of 5 average rating, 313 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.

KitchenIndoor spacesHiking

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, 253 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 out of 5 average rating, 263 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.

Indoor spacesKitchenWi-Fi

Campervan/RV in Louisville

The interior of the Airstream features a bright and modern layout. A well-equipped kitchen is visible on the left, including a stove and sink. A cozy sitting area with a light-colored couch is present, while a sleeping area is seen towards the back, adorned with soft bedding.

4.98 out of 5 average rating, 150 reviews

The Marie Airstream at Progress Park in Derby City

Marie is a 1996 Excella, perfect for groups, families, or midweek getaways.Skip the packing & extra costs - everything you need is already here. Maire 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. 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.

FamilyKitchenBeach

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, 233 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 spacesFamilyLocation

4.98 out of 5 average rating, 257 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.

FamilyKitchenAir conditioning

4.97 out of 5 average rating, 148 reviews

The bedroom features a spacious king-sized bed, adorned with decorative pillows, and a stylish ceiling fan above. A wooden chest sits at the foot of the bed, complemented by a desk and chair in the corner. Natural light enters through window treatments, illuminating the room.

Guesthouse in Louisville

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

KitchenIndoor spacesAccess

A stylish living area features a modern gray sofa accompanied by two blue accent chairs. A large flat-screen TV is mounted above a black fireplace. Natural light enters through multiple windows, which frame views of the surrounding greenery, enhancing the room's serene ambiance.

4.98 out of 5 average rating, 136 reviews

Charming Bungalow on 1.5 Acres in Amazing Location

Peaceful. Private. Clean. Comfortable. Convenient. Hummingbird is a charming updated bungalow in one of Louisville's most coveted neighborhoods. Nestled on 1.5 acres of a historic street, you'll enjoy a park-like setting teeming with wildlife. Private, yet offering easy access to shopping, dining, entertainment, and major highways, this hidden gem is sure to please. Whether here work, fun, or both, you’ll love your time at Hummingbird.

Indoor spacesFamilyDecor

A spacious living area features a large sectional sofa arranged around a circular coffee table. A neutral-colored wall holds a decorative fireplace, while soft lighting creates a relaxed setting. A television and desk are positioned on one side, enhancing the room's functionality.

4.97 out of 5 average rating, 188 reviews

Newly Updated: Spacious Suite/Private Entry

My guest suite is close to restaurants, business parks, shopping and easy access to highways. Guests love this place because of the big trees, green space and private entrance. The patio is great for sipping morning coffee, reading or enjoying an evening beverage. Beautiful, quiet neighborhood is perfect for a walk/run. This spacious, comfortable suite is good for couples, solo adventurers, business travelers and small families.

FamilyIndoor spacesQuiet

4.93 out of 5 average rating, 1,237 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

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.

Indoor spacesKitchenCheckout

Popular amenities for Middletown family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 102 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

Indoor spacesKitchenGetting around

4.98 out of 5 average rating, 259 reviews

A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.

Cabin in Lawrenceburg

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

KitchenIndoor spacesQuiet

4.91 out of 5 average rating, 148 reviews

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

KitchenFamilyWi-Fi

4.98 out of 5 average rating, 153 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 spacesAccuracy

4.97 out of 5 average rating, 384 reviews

The exterior of the estate features a charming porch adorned with potted plants and a flag. Sunlight filters through the surrounding trees, illuminating the stone and wood structure. A stone pathway leads through the lush green lawn, enhancing the inviting outdoor space.

Cabin in Henryville

Close to Louisville~Hot Tub~Fire Pit~Game Room

Indoor spacesKitchenTV

4.95 out of 5 average rating, 206 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

FamilyIndoor spacesLaundry

4.97 out of 5 average rating, 119 reviews

Cabin in Shepherdsville

Bourbon Cabin - Speakeasy/HotTub/Arcade/Derby

KitchenFamilyValue

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 spacesBackyard

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 122 reviews

3BR Home Near Zoo & Fairgrounds – Family-Friendly!

KitchenIndoor spacesNearby

Superhost

Apartment in Louisville

4.84 out of 5 average rating, 157 reviews

NEW! Cozy, Private Highlands Studio

Indoor spacesKitchenLocation

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, 343 reviews

Quiet Neighborhood Home With Outstanding Location

KitchenIndoor spacesLayout

4.94 out of 5 average rating, 750 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

Indoor spacesFamilySleep quality

Apartment in Saint Matthews

An exterior view of the private apartment building features a welcoming entrance with a covered porch and an attractive staircase leading to the second floor. Surrounding greenery enhances the setting. Designated parking spaces are visible, with wheelchair accessibility indicated.

4.95 out of 5 average rating, 110 reviews

Swanky Fully Equipped St. Matthews Apartment

FamilyIndoor spacesLayout

A comfortable living area features a light grey sofa and two matching armchairs, arranged around a circular coffee table on a textured area rug. A ceiling fan hangs above, and natural light filters through the large window, illuminating black and white framed photographs on the walls.

5 out of 5 average rating, 144 reviews

Quaint Highland's Bungalow

FamilyIndoor spacesComfort

A spacious living area features large windows allowing natural light to fill the room. A comfortable couch and a reclined chair offer seating, with a coffee table in front. A fireplace serves as a focal point, framed by decorative elements and bookshelves.

4.96 out of 5 average rating, 318 reviews

Home near the Highways

KitchenIndoor spacesLaundry

4.94 out of 5 average rating, 798 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

Indoor spacesKitchenBarbecue

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, 404 reviews

Cherokee Park Oasis with Pool and Hot Tub

FamilyIndoor spacesBathroom

5 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

KitchenFamilyWalkability

Apartment in Central Business District

A modern bedroom features a cozy king bed with soft linens, a comfortable sofa, and a patterned area rug. Natural light filters through the large windows, with a green plant adding a touch of nature. Soft lamps provide additional lighting, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 341 reviews

4th Street Suites - Deluxe King Bed Suite

KitchenFamilyDecor

4.95 out of 5 average rating, 222 reviews

Luxury Retreat with Hot Tub

FamilyIndoor spacesWalkability

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.

4.83 out of 5 average rating, 127 reviews

Lake Livin' & Bourbon Sippin'

FamilyIndoor spacesGetting around

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.

4.99 out of 5 average rating, 152 reviews

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

FamilyIndoor spacesBarbecue

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, 188 reviews

The Gathering Place

KitchenIndoor spacesBarbecue