Family-friendly vacation rentals in Middletown

Guest suite in Cherokee Triangle

A contemporary exterior features a striking navy blue facade with geometric accents. Two entrance doors are framed by lush greenery, including neatly trimmed shrubs and tall grasses. Large windows allow natural light to fill the interior, while architectural details highlight the property's modern design.

4.97 out of 5 average rating, 147 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Guest suite in Schnitzelburg

A compact seating area is presented with a gold quilted cover on a sofa bed, alongside a framed artwork and calendar on the wall. A round mirror is mounted nearby, and an air conditioning unit is discreetly placed above the comfortable seating.

4.83 out of 5 average rating, 245 reviews

TINY WUNDERHAUS - A Fun, Hometown Experience

Tiny Spaces are all the rave; Here's a chance to try one. In the heart of Louisville's historic Schnitzelburg, an up and coming area full of neat shotgun cottages, whitewashed, and many historic Louisville pubs. It's only 3.5 miles from downtown and approx. 2 from Churchill Downs. It has a full kitchen, bath, in-unit washer/dryer, and sleeping space for 3 adults. This apartment is sure to meet every vacation need. The comfort-tested mattresses are both new with 1.5 - 2in. memory foam toppers.

4.95 out of 5 average rating, 349 reviews

A charming log cabin is framed by lush green trees, showcasing a warm exterior with a stone chimney. Rocking chairs are placed on the front porch, surrounded by vibrant flowers and a neatly maintained garden path leading to the entrance.

Cabin in Louisville

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

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.

4.94 out of 5 average rating, 297 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.

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, 207 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!!

4.98 out of 5 average rating, 248 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.

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, 219 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.

4.81 out of 5 average rating, 679 reviews

An open loft space features a spacious bed with a blue accent blanket. A comfortable sofa sits opposite a stylish dining area, adorned with a round table set for six. Large windows allow natural light to brighten the wooden flooring and inviting decor.

Loft in Louisville

DerbyLoft Louisville

Enjoy the best of Louisville in our second floor loft, a studs-up renovation with modern amenities, full kitchen, and a beautiful bathroom. We're in a central location from which guests can easily tour the heart of Louisville. Private entrance Free parking on street Free Wifi 10min (0.5mi) walk to Churchill Downs 25min (1.5mi) walk to Cardinal Stadium 5min (1.8mi) drive to historic Old Louisville 6min (1.9mi) drive to KY Expo Center 12min (3.2mi) drive to Louisville Airport

4.97 out of 5 average rating, 328 reviews

The interior space of the Airstream showcases a modern design with reclaimed wood floors and white walls. A spacious kitchen features concrete countertops and various appliances. A cozy seating area includes a daybed, while the rear sleeping area is softly illuminated, creating a comfortable atmosphere.

Camper/RV in Louisville

The Grace Airstream at Progress Park in Derby City

Always wanted to experience the vintage airstream life? Here's your chance! The Grace is a 1974 Airstream Sovereign Land Yacht. All the amenities of a hotel, just on the water's edge. Enjoy your coffee in the hammock, spend your days hiking, fishing, swimming, kayaking or paddle boarding. A hidden gem, right in the city. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

4.97 out of 5 average rating, 246 reviews

A patio area features several blue chairs positioned on a textured surface, with a stone bench visible nearby. Lush green trees surround the space, providing a natural backdrop. In the distance, a red structure can be seen, framed by the greenery.

Guest suite in Prospect

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

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, 213 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.

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.

4.93 out of 5 average rating, 153 reviews

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.

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, 192 reviews

The cabin exterior is nestled within a wooded landscape, showcasing a wooden facade. A welcoming porch is framed by two Adirondack chairs, with stepping stones leading toward the entrance. Twinkling lights hang across the trees, enhancing the tranquil evening ambiance.

Cabin in Lawrenceburg

Chic Cabin w/ Trails, Hot Tub & Starry Nights

5 out of 5 average rating, 219 reviews

The exterior of the Shantyboathouse is presented, featuring a two-story blue structure with white trim and a welcoming patio area below. The backyard offers comfortable seating and a grill, while greenery lines the edges. The upper deck is accessible, providing additional outdoor space for relaxation.

Home in Butchertown

Butchertown & NuLu's Shantyboathouse

4.99 out of 5 average rating, 103 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

Apartment in Central Business District

A bright bedroom features a spacious bed with a red throw blanket and neatly rolled towels. Two bedside tables with stylish lamps flank the bed. Three abstract art pieces hang on the wall above, while large windows provide natural light and a view of the outside.

4.92 out of 5 average rating, 116 reviews

Elegant Apt – King Bed, Heated Pool, Gym + Hot Tub

A private hot tub is situated on a paved area, surrounded by a wooden fence for added privacy. Colorful flower pots with blooming flowers are positioned nearby, complementing the fresh green grass. Two red chairs sit in the backyard, inviting relaxation.

4.99 out of 5 average rating, 267 reviews

Fall Haven - King Beds, Hot Tub

4.97 out of 5 average rating, 350 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

4.92 out of 5 average rating, 119 reviews

A cozy outdoor firepit area is surrounded by Adirondack chairs, arranged in a circle on a gravel surface. Soft, warm lights hang overhead, illuminating the space against a serene, wooded backdrop, creating an inviting atmosphere for gatherings.

Villa in Prospect

Bourbon Trail, Firepit

4.98 out of 5 average rating, 174 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*Pewee Valley *HOT TUB

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 1,096 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

A cozy seating area features a daybed with colorful cushions and a contrasting metal chair. A gas fireplace is positioned beside a television, which is mounted above a decorative stone surround. Vintage decor elements, including signs and lamps, enhance the inviting space.

4.94 out of 5 average rating, 337 reviews

Highlands Lower Level Studio Guest Suite

Superhost

The exterior features a two-story white house with a red front door, surrounded by greenery. A concrete pathway leads to the entrance, and a spacious driveway complements the landscape. Soft outdoor lighting highlights the home's contemporary design during dusk.

Home in Simpsonville

4.91 out of 5 average rating, 127 reviews

Comfortable sleek home bourbon trail

4.92 out of 5 average rating, 180 reviews

A cozy living area is showcased with a vibrant purple sofa and a plush ottoman. A wooden television stand supports a flat-screen TV, while natural light floods in through a window. Colorful decor elements hang from the sloped ceiling, adding a playful touch.

Loft in Germantown

Germantown cozy apartment

4.95 out of 5 average rating, 746 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

A welcoming living area features a light blue wall and hardwood floors. A large sectional sofa is positioned next to a coffee table. A clock adorns the wall, and recessed lighting illuminates the space. The adjoining area includes a dining table visible in the background.

4.99 out of 5 average rating, 176 reviews

Newly Renovated Derby House

Guest suite in Kenwood Hill

A spacious living area features comfortable seating arrangements, including a blue fabric sofa and two patterned armchairs. A wooden coffee table sits centrally, with magazines and a small vase. The open kitchen area is visible in the background, equipped with modern appliances.

4.95 out of 5 average rating, 116 reviews

Walkout on wooded hillside by Airport and Downs

4.95 out of 5 average rating, 147 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

Family-friendly home rentals with a pool

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, 388 reviews

Cherokee Park Oasis with Private Entrance

4.91 out of 5 average rating, 137 reviews

A charming two-bedroom cottage is displayed, featuring a combination of gray siding and a peaked roof. The front porch is accessible via a small set of steps, surrounded by manicured grass and shrubs. Nearby trees provide a touch of greenery against a clear blue sky.

Cottage in Taylorsville

Best view of the lake two bed two bath cottage #4

Cottage in Spencer County

Aerial view captures Taylorsville Lake, surrounded by lush greenery and autumn foliage. The winding shoreline is visible alongside the marina with several boat docks. The community road runs beside the scenic landscape, providing a clear view of the serene water and rolling hills.

4.92 out of 5 average rating, 159 reviews

Peaceful Cottage Minutes from Lake Access

5 out of 5 average rating, 119 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

Peppermint Cottage Norton Commons w Breakfast

4.94 out of 5 average rating, 226 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

4.97 out of 5 average rating, 205 reviews

Cottage in Taylorsville

Luxury Retreat with Hot Tub

4.85 out of 5 average rating, 110 reviews

A view of the Ohio River is captured, featuring the downtown Louisville skyline in the background. A bridge spans the river, while a scenic waterfront area is visible with well-maintained greenery and a line of parked vehicles along the street.

Condo in Jeffersonville

Spacious Riverfront Condo Minutes from Downtown!