House holiday rentals in Middletown

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, 322 reviews

Home near the Highways

Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

The open living area showcases hardwood floors and features natural light from large windows. A leather couch is positioned beside a wooden coffee table. The modern kitchen includes a spacious island with bar seating for six, complemented by white cabinetry and stainless steel appliances.

4.98 out of 5 average rating, 297 reviews

The Lakehouse at Progress Park in Derby City

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The Lake 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.

5.0 out of 5 average rating, 266 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.

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, 260 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!

5.0 out of 5 average rating, 131 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

Step into Peppermint Cottage ( breakfast included) and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, 3 pools and YMCA. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and summer Friday food trucks with live music . Your Louisville adventure awaits !

4.91 out of 5 average rating, 160 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.

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, 138 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.

4.93 out of 5 average rating, 179 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.

Home in East Market District

Butchertown 1BR | Walk to NuLu | Free Parking

Stay in Louisville's Historic Butchertown, just steps from the restaurants, breweries, boutiques, and bourbon experiences of NuLu. This beautifully renovated first-floor 1-bedroom apartment combines historic character with modern comfort, featuring soaring 11-foot ceilings, exposed brick chimneys, a spacious open-concept living area, a fully equipped kitchen, dedicated workspace, Smart TVs, and free parking for a convenient city stay.

4.88 out of 5 average rating, 149 reviews

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, 189 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.

A large wooden dining table is centered in the room, surrounded by wooden chairs. Two framed vintage world maps hang on the walls, adding an earthy tone to the space. A simple vase with greenery sits atop the table, enhancing the natural decor.

4.98 out of 5 average rating, 212 reviews

"The Brook" - Louisville

Enjoy a stay at this spacious, beautifully decorated ranch home in East Louisville. Blending organic modern decor and intentional functionality, you will feel relaxed and right at home. The home is nestled in a quiet neighborhood and yet only 1 mile from the interstate - conveniently located, a drive anywhere isn't far. Bring your crew to town to experience a day at the horse track, a bourbon tour, or a Kentucky family getaway!

The entrance features a black door with an oval window, framed by decorative brick. Two potted topiaries are placed alongside the door, while a wicker chair with a patterned cushion sits to one side. Warm outdoor lighting is provided by wall-mounted lanterns.

4.92 out of 5 average rating, 113 reviews

...Happy Trails House in Derby City

4 bedroom, 2 full baths, 1 half bath, ( bedrooms on 2nd floor, none on 1st floor ). Our home is on a dead end street steps away to a walking trail, fenced yard, 2 patios, charcoal grill. Only 15 to 20 min. drive to Downtown, Churchill Downs, Hospitals, Airport, close to major highways. Near restaurants, shopping centers, grocery, liquor store etc. pets welcome with $10 fee per pet per night. Washer/dryer and dishwasher

Popular amenities for Middletown house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 107 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

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!

4.91 out of 5 average rating, 108 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

Superhost

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

4.83 out of 5 average rating, 105 reviews

4.89 out of 5 average rating, 137 reviews

Home in Taylorsville

#18 Kentucky Sunrise - Lakefront Home with spacuio

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.

4.95 out of 5 average rating, 37 reviews

The Getaway!

4.99 out of 5 average rating, 70 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

Superhost

A modern living space features a comfortable brown leather sofa and two accent chairs. A stylish area rug lies on the floor, while built-in shelves display decorative items and books. Natural light streams through large windows, illuminating the room's inviting atmosphere.

4.86 out of 5 average rating, 7 reviews

Luxury: Private Pickleball, Tennis, Pool, & Hottub

Weekly house rentals

An open kitchen area features warm wooden cabinetry and stainless-steel appliances. A dining table with black chairs is centered in the space, while a welcoming sign adorns the wall. Natural light brightens the room, highlighting the hardwood flooring and decorative elements.

4.92 out of 5 average rating, 133 reviews

Centrally Located•4 Bedrooms•2 Full Baths•Backyard

4.91 out of 5 average rating, 210 reviews

A welcoming living area features a brown leather sofa and a light-colored armchair, arranged around a circular coffee table. A large window allows natural light to fill the space, and a wall-mounted TV is positioned opposite the seating. A fan is mounted on the ceiling.

Home in Jeffersonville

Scandinavian Retreat: Cozy Stay near Louisville

The living area features a comfortable dark gray couch, an accent coffee table with a vintage trunk design, and two bright orange chairs. Natural light filters through large windows, accentuated by soft blue curtains. A colorful area rug adds warmth, with decorative wall art enhancing the space.

4.91 out of 5 average rating, 179 reviews

The Jungalow: 65" 4K TV, memory foam, kid-friendly

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.

4.88 out of 5 average rating, 243 reviews

Private EAST END gem, minutes to everything!

4.96 out of 5 average rating, 105 reviews

The living room features a classic design with rich green walls and a mix of hardwood and patterned flooring. Two ornate armchairs are positioned opposite a dark wood coffee table, with a leather sofa off to the side. Large windows allow natural light to fill the space.

Home in La Grange

The Lady Jinx Home - 3 BR/2.5 Bath - Entire Home

A spacious living area features a comfortable gray sectional sofa, accented by decorative pillows. A round coffee table sits at the center on a striped rug. Tall windows allow natural light to fill the room, while a brick fireplace adds warmth, complemented by wall decor.

4.95 out of 5 average rating, 103 reviews

Spacious 4 BD Home | 5 min to Airport • 6 min Expo

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.

4.94 out of 5 average rating, 181 reviews

The River's Edge Oasis, close to downtown

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, 348 reviews

Quiet Neighborhood Home With Outstanding Location

Private house rentals

A cozy TV room features a stone fireplace as its focal point, flanked by built-in shelves containing books and decorative items. A black armchair with a light throw sits invitingly in the corner, with warm wooden flooring throughout the space.

4.96 out of 5 average rating, 47 reviews

The Blackacre Getaway

4.93 out of 5 average rating, 14 reviews

Home in Jeffersontown

Bourbon Trail Estate | 3 Epic Acres | 7 Bed 6 Bath

4.93 out of 5 average rating, 42 reviews

An open kitchen and dining area features modern appliances and a spacious dining table with multiple chairs. Sunlight pours through large windows, offering views of the outdoor landscape. A cozy seating area with neutral-colored cushions and decorative pillows is positioned nearby.

Home in Crestwood

Garden House, a private getaway

4.93 out of 5 average rating, 28 reviews

Louisville Getaway

Superhost

A well-lit recreational room features a pool table at its center, surrounded by windows that allow natural light. Colorful pool balls are arranged on the table, and wall decor includes playful circular elements. A door leads to an outdoor space, enhancing accessibility.

Home in Jeffersontown

Safe, comfortable, convenient, hot tub, fire pit!

4.76 out of 5 average rating, 58 reviews

5.0 out of 5 average rating, 96 reviews

An open-concept living area features a cozy sofa and armchair, with light-colored walls and wooden beams above. The modern kitchen, equipped with stainless steel appliances and a spacious island, is complemented by bar seating and a view of the outdoors through a window.

Home in Crestwood

Briar Creek Cottage

4.97 out of 5 average rating, 36 reviews

Newly Renovated 5BR • 2 Living Rooms • Sleeps 10