Holiday rentals with a patio in Middletown

4.99 out of 5 average rating, 185 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

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

Guest suite in Jeffersonville

An outdoor fire pit is surrounded by several wooden chairs, providing a gathering space for relaxation. The calm waters of the Ohio River reflect the night sky, with soft lights from boats creating a serene atmosphere. Low greenery and gentle clouds frame the scene.

4.95 out of 5 average rating, 233 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

4.9 out of 5 average rating, 102 reviews

The front view of the newly renovated house features a white exterior with black trim and a central entrance. A brick porch with inviting planters frames the entryway, while a navy-colored door adds contrast to the facade.

Home in Jeffersonville

Little Luxury in Jeffersonville

VisitJeff & Louisville and stay in this newly renovated home! 1 Bed/1 bath. Fenced in patio area & private driveway. Walk to parks, dining & shopping in downtown Jeffersonville. High ceilings, quaint space, modern ammenities! New chef's kitchen, dining table, island seating, queen size bed, comfy couch, LUXURY bathroom w stand alone soaker tub, shower & plenty of vanity space! Perfect for 2 guests (and or a child ) Washer and dryer. We live near by & have another Air B N B across the street!

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

After a beautiful drive along a tree-lined-canopied road, you will find Mint Julep Villa, located on a private 1.3 acre lot and just one street over from the Ohio River. Mint Julep Villa, is tastefully decorated for you and your family to enjoy your stay in the Louisville and Prospect KY area. No matter if it's the Bourbon trails, the Kentucky Derby, the numerous concerts and the many other attractions to draw you to Kentucky, Mint Julep Villa will be a place you'd be attracted to as well.

4.99 out of 5 average rating, 203 reviews

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.

Home in Louisville

"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!!

4.99 out of 5 average rating, 243 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.

Apartment in Central Business District

The living area features a modern design, anchored by a dark leather sofa adorned with colorful throw pillows. Two elegant armchairs flank a low, wooden coffee table. A large black-and-white artwork adorns the wall above, while natural light filters through large windows, illuminating the warm, earthy tones.

4.94 out of 5 average rating, 121 reviews

4th Street Suites - Serene King Bed Suite

Live the best of Louisville in this sleek 1‑bed, 1‑bath downtown retreat! Perfect for couples, families, or friends, it features a cozy king bed, 2 rollaways, a fully stocked kitchen, and a bright living area. Enjoy morning coffee or evening drinks on your private balcony, stroll to nearby restaurants and bars, then relax by the pool or hot tub, play a round in the golf simulator, or unwind with a game of pool. Your launchpad for adventure—or a quiet, stylish escape when it’s time to rest!

4.91 out of 5 average rating, 204 reviews

The home's inviting facade features white clapboard siding and large front windows adorned with classic trim. A welcoming entrance is highlighted by a beautiful door, surrounded by potted flowers and greenery. The well-maintained yard includes a small walkway that leads to the entrance.

Home in Highlands

Cheerful, centrally located 2 bedroom shotgun home

This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

4.92 out of 5 average rating, 195 reviews

A modern kitchen area features stainless steel appliances, including a refrigerator and dishwasher, complemented by white cabinetry. A cozy living space is visible with a comfortable sofa and a coffee table, while natural light enters through a sliding glass door leading to a small balcony.

Apartment in Clarksville

Modern stay overlooking downtown

Forget your worries in this Luxury spacious and serene space. Make yourself at home! Relax in the unique 1Bedroom Queen size bed with Restaurants and smoothie bar in building! you’ll be close to Restaurants alongside the Ohio river, Kfc Yum Center, Downtown Walking bridge , Deserts , bars , music and more! Great wifi, meeting rooms open 24/7 charging stations for your electric vehicle! Last but not least Beautiful overlook of downtown Louisville on charming rooftop patio!

4.84 out of 5 average rating, 103 reviews

A cozy living area features a light beige sectional sofa adorned with a white pillow and a brown accent pillow. A sleek stainless steel refrigerator stands beside modern kitchen cabinetry. Two framed artworks depicting serene waves are displayed on the wall, enhancing the inviting space.

Apartment in Clarksville

Beach Vibe close to Museum Row

Grand Opening!!! The beach vibes here are amazing 🤩! This special place is close to everything, making it easy to plan your visit. Only 2.7 mile away you will enjoy everything Downtown Louisville has to offer from a Bourbon Experience, great places to eat, bars, museums, arts, theater, music on Main Street also known to locals as Whiskey Row and Museum Row. Enjoy the local Indiana scene in Downtown Jeffersonville or Downtown New Albany with food and fun!

4.98 out of 5 average rating, 141 reviews

A comfortable sleeping area features a well-made bed with soft linens and a decorative throw pillow. Two bedside tables with turquoise lamps provide soft lighting. Tall curtains frame the window, allowing natural light to fill the space while offering a glimpse of greenery outside.

Apartment in Louisville

Haus on Speed, charming 2nd floor apartment

Welcome to the Haus on Speed! Please note that if you have mobility issues, the apartment is on the 2nd floor and you will need to be able to climb about 20 carpeted steps. There are also 6 exterior steps when walking up from the sidewalk. Walk to anything from our charming 100+ year old Highlands home in one of Louisville's more vibrant & loved neighborhoods! This home is thoughtfully furnished to include all the comforts you could need during your stay.

4.99 out of 5 average rating, 170 reviews

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.

Home in Louisville

"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!

Popular amenities for Middletown Holiday Houses with Outdoor Verandahs

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

Apartment in Shepherdsville

A spacious living area features a black leather sectional sofa and a wooden bar with stools. Tile flooring extends throughout the room, which is illuminated by ceiling lights. Walls are decorated with framed artwork, and there are double doors leading to a closet.

4.92 out of 5 average rating, 145 reviews

For the ones who serve

5 out of 5 average rating, 20 reviews

Apartment in Brooks

Cozy Studio in Brooks

Apartment in New Albany Downtown Historic District

An open-concept kitchen area showcases modern cabinetry and stainless steel appliances. A curved counter with seating for three is highlighted, alongside a stove and stylish light fixtures. The room is brightened by natural light, creating a welcoming and functional space.

4.99 out of 5 average rating, 113 reviews

Luxury 1BR Apt w King Bed near Louisville KY

4.97 out of 5 average rating, 71 reviews

A spacious great room features a comfortable sectional sofa and two patterned armchairs, arranged around a round glass coffee table. A wall-mounted television and decorative shelves are seen in the background. Natural light enters through multiple windows, illuminating the stylish decor and flooring.

Apartment in Louisville

second floor 1 bedroom + office W/D & easy parking

4.97 out of 5 average rating, 78 reviews

A modern living area is showcased, featuring a blue sofa positioned toward a wall-mounted television. A bright, colorful wall art piece adds a touch of character. Natural light filters through large windows, offering a view of the balcony area.

Apartment in Clarksville

Studio Apt Near Downtown Louisville

Apartment in Central Business District

A living area features a dark leather sofa and a patterned area rug. A coffee table sits at the center, with a teal cup on top. Light fills the space from large glass doors that open to a balcony, and a modern kitchen is visible in the background.

4.96 out of 5 average rating, 145 reviews

Falls City Loft - Free parking!

4.87 out of 5 average rating, 159 reviews

A modern kitchen and living area feature hardwood flooring and natural light from large windows. The kitchen includes a central island with two barstools, stainless steel appliances, and a convenient laundry area. A cozy couch with decorative pillows provides a comfortable seating option.

Apartment in Vine Grove

Vine Grove with fire pit/play set

Apartment in Central Business District

A light-filled living area features a comfortable sofa adorned with soft throw pillows and a cozy blanket. A modern coffee table displays a decorative arrangement of flowers, while a colorful artwork of a tree enhances the inviting atmosphere. Large windows provide views of the surrounding buildings.

4.96 out of 5 average rating, 124 reviews

Downtown Chic Apt – King Bed, Gym, Pool & Hot Tub

Holiday House Rentals with a Verandah

4.94 out of 5 average rating, 123 reviews

A vibrant bedroom is presented with a spacious bed dressed in a white comforter. A decorative headboard is paired with side tables featuring lamps. The walls are adorned with colorful art, enhancing the room's character, while natural light filters through a window with sheer curtains.

Home in New Albany

Bright, fun, and colorful home

4.81 out of 5 average rating, 149 reviews

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.

Home in Camp Taylor

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

4.99 out of 5 average rating, 128 reviews

A modern living area is presented with a grey sofa accented by patterned cushions. A light marble coffee table is centered on a patterned rug. A potted plant adds a touch of greenery, while natural light streams through window treatments, illuminating the space.

Home in Jeffersonville

Lil Blue-Cheerful, fully renovated & updated home

4.92 out of 5 average rating, 289 reviews

A cozy living room features large windows dressed in light curtains, allowing natural light. A flat-screen television is mounted above a brick fireplace. A small table with potted plants sits beside a comfortable armchair, and a wooden coffee table occupies the center of the space.

Home in Camp Taylor

Camp Taylor Hideaway Close to Audubon Hospital

4.92 out of 5 average rating, 141 reviews

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.

Home in Louisville

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

4.96 out of 5 average rating, 246 reviews

A modern living area is furnished with a green sofa adorned with cushions. Above, framed botanical artwork decorates the wall. An open kitchen is visible, featuring stainless steel appliances and light wood shelving, complemented by a small dining table.

Home in New Albany

The Green House in Downtown

4.92 out of 5 average rating, 159 reviews

The kitchen features modern appliances, sleek cabinetry, and a large island with bar seating. A pendant light hangs above, highlighting the open space. Wooden beams adorn the ceiling, adding character to the area. Natural light streams through the window, enhancing the neutral color palette.

Home in Germantown

Germantown gem w/ private parking & fenced in yard

Home in Smoketown Jackson

An inviting open-air living room features a pool table with colorful billiard balls awaiting play. Plush velvet couches in green and gold surround a circular coffee table, set against a backdrop of exposed brick walls. The space is brightened by large windows and artistic wall decor.

4.94 out of 5 average rating, 217 reviews

"Blue Grass" Pool Table Retreat - Plush Comfort

Holiday condos with a patio

4.92 out of 5 average rating, 59 reviews

The living room features a cozy arrangement with a light-colored sectional sofa and a coffee table on a decorative rug. A flat-screen TV is mounted above a modern fireplace, while built-in shelves display various decorative items. The kitchen is visible in the background.

Condo in Highlands

Perfect Location! Huge Space in Walkable Highlands

4.93 out of 5 average rating, 169 reviews

A dining area features a modern table surrounded by orange chairs, placed on a textured rug. Wall art with floral designs adds color to the space, while a mounted television is visible. A small side table with decorative items is positioned nearby.

Condo in Jeffersonville

Cozy penthouse with entertainment and food nearby

Condo in Cherokee Triangle

A modern kitchen is visible, featuring stainless steel appliances and navy blue cabinetry. Natural light floods the space through large windows, illuminating a dining table with seating for four. A cozy living area is adjacent, furnished with a gray sofa and a patterned area rug.

5 out of 5 average rating, 7 reviews

Luxury 1-Bed Oasis In Heart Of Highlands W/ Free P

Condo in Central Business District

5 out of 5 average rating, 21 reviews

Bitters Suite-New on Bourbon Trail! BRAND NEW!

Condo in Cherokee Triangle

A cozy bedroom is presented, featuring a spacious bed covered with a handmade quilt. Two bedside tables with lamps flank the bed, while natural light enters through window treatments on either side. A ceiling fan adds comfort to the serene space.

4.94 out of 5 average rating, 17 reviews

Cherokee Park / Highlands Charm

Condo in East Market District

A spacious living area features large windows allowing natural light to fill the room. A modern gray sofa is accompanied by two green accent chairs. A stylish coffee table sits in the center on a textured rug. A gallery wall displays a collection of framed black and white photographs.

4.94 out of 5 average rating, 83 reviews

2BR | 2BA - Downtown Apt in NuLu w Private Parking

4.8 out of 5 average rating, 5 reviews

A two-story building is shown, featuring a covered porch that wraps around the front. The exterior walls are painted white, contrasted by black trim. A large yard and open fields surround the property, with clear blue skies overhead.

Condo in New Castle

The Bunker