Vacation rentals with a patio in Shelbyville

4.98 out of 5 average rating, 251 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

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)

The exterior of the remodeled house is framed by lush trees, showcasing a welcoming deck with ambient lighting. A traditional barrel sauna is positioned nearby, blending with the natural surroundings. The inviting façade reflects warm tones, enhanced by the soft glow of the setting sun.

4.99 out of 5 average rating, 124 reviews

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

4.97 out of 5 average rating, 184 reviews

The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.

Home in Lawrenceburg

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

4.99 out of 5 average rating, 159 reviews

A paved driveway stretches into the distance, flanked by lush green grass and a large tree. Wooden fencing borders the property, offering views of rolling hills and a colorful sunset sky above.

Farm stay in Frankfort

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & campfires.

4.99 out of 5 average rating, 122 reviews

Backyard Bourbon Retreat

Your family will be close to everything when you stay at this centrally-located place. This is a beautiful two bedroom two full bath home packed with a ton of amenities! Only minutes from several distilleries such as Buffalo Trace, Jim Beam, Woodford Reserve, Ancient Age and Four Roses just to name a few! There is a fully fenced in yard with a deck looking into a 1/4 acre landscaped backyard. Great for sitting back and relaxing with a Kentucky beverage. Welcome to the Backyard Bourbon Retreat!

4.98 out of 5 average rating, 306 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.

4.99 out of 5 average rating, 566 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!

Superhost

Home in La Grange

4.91 out of 5 average rating, 139 reviews

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

A charming exterior view of a two-story bungalow features blue-green siding and a welcoming front porch. American flags are displayed, while flower beds with various plants enhance the landscaped front yard. The stone walkway leads to the entrance, inviting visitors to approach the home.

4.98 out of 5 average rating, 101 reviews

The Crafty Bourbon Bungalow Apartment

The Crafty Bourbon Bungalow Apartment is located in the historic district of Frankfort just three blocks from the Capitol and within walking distance of downtown shops and restaurants. We are in the heart of horse and bourbon country with easy access to local distilleries and racetracks. The apartment has a private entrance, one parking space, two bedrooms with queen beds, one bath with claw tub/shower combo, kitchenette and an eating and sitting area.

4.97 out of 5 average rating, 155 reviews

Two wooden Adirondack chairs are positioned around a stoned fire pit, overlooking a tranquil lake. The scene features lush greenery and a group of ducks gently swimming in the water, complemented by a boathouse and kayaks in the background.

Cabin in Lawrenceburg

Bourbon Trail Bliss by the Lake, HotTub, Kayaks

Welcome to Your Ultimate Lakeside Retreat! Nestled on the renowned Bourbon Trail in the heart of The Kentucky Bluegrass, our spacious cabin offers a perfect blend of tranquility and adventure, while providing a place to connect with the people that mean the most. Whether you're a couple, a family, or a group of friends, there is something for everyone. Savor your memories like a perfect glass of aged whiskey at Bourbon Bliss by the Lake.

4.98 out of 5 average rating, 157 reviews

Home in Bagdad

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

Brand-new luxury farmhouse on 5 private acres in the heart of Kentucky bourbon country. This 4BR retreat sleeps 12 and is built for unforgettable group getaways, with a massive game room, full bar, pool table, shuffleboard, foosball, poker table, 85” TV, covered 6-person hot tub, huge firepit, outdoor games, and a fully stocked chef’s kitchen. Minutes from Buffalo Trace, Bulleit, and Jeptha Creed. Send us a message with any questions!

5.0 out of 5 average rating, 153 reviews

A log cabin is set against a vibrant sunset, highlighting its wooden exterior and spacious porch. Lush green grass surrounds the cabin, complemented by flower beds and gravel pathways. The rear showcases windows and entrance doors that invite natural light into the home.

Cabin in Frankfort

Sip on bourbon in the hot tub! +hiking & game shed

A charmingly unique taste of KY waits for you at this peaceful log cabin! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plentiful amenities on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!

Popular amenities for Shelbyville patio rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

Apartment in Central Business District

A spacious living area is highlighted by expansive floor-to-ceiling windows, offering views of the cityscape. Modern furnishings include a sectional sofa, a coffee table, and stylish chairs. A decorative light fixture hangs overhead, complementing the wood flooring and neutral-toned walls.

4.92 out of 5 average rating, 138 reviews

Location! Corner downtown condo!

4.99 out of 5 average rating, 108 reviews

A cozy bedroom features a spacious bed with a textured white coverlet. An illuminated headboard casts a soft glow, while a decorative tray with a candle and a small plant is placed on the bed. Black and white accents enhance the calming atmosphere.

Apartment in Clarksville

Flawlezz Stays

4.98 out of 5 average rating, 171 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

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, 200 reviews

Falls City Loft - Free parking!

4.99 out of 5 average rating, 135 reviews

A cozy living area features large windows allowing natural light to fill the space. A comfortable gray sofa is complemented by accent chairs. A coffee table sits in front of the seating area, and a modern kitchen island with a sleek countertop is in the foreground.

Apartment in New Albany

Downtown Luxury 1BR Apt near Louisville KY

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.

4.93 out of 5 average rating, 174 reviews

For the ones who serve

Apartment in East Market District

An inviting entryway showcases an assortment of framed artwork and photographs. A wicker chair is positioned beside a small table with a lamp. The view opens to a warm living area filled with natural light, with soft decor and a glimpse of a dining space in the background.

4.97 out of 5 average rating, 190 reviews

An Unhurried Stay in Butchertown · Steps from NuLu

Superhost

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

4.84 out of 5 average rating, 126 reviews

Beach Vibes 2 mile to Whiskey Row Bourbon City

House rentals with a patio

4.96 out of 5 average rating, 122 reviews

The image collage features various spaces of a stylish home. A cozy lounge area with a fireplace is shown, alongside an outdoor hot tub surrounded by greenery. The dining area is connected to a deck, and a game room with a bar creates an inviting entertainment space.

Home in Bardstown

StillHill: HotTub GameRoom Whiskey Lounge Acreage

4.99 out of 5 average rating, 107 reviews

A serene sunset is captured over rolling hills, where the sun casts warm orange and yellow tones across the sky. Wispy clouds are visible, enhancing the natural beauty of the horizon. The foreground features lush greenery, creating a peaceful ambiance.

Home in Floyds Knobs

Home with Breathtaking View

4.93 out of 5 average rating, 111 reviews

A covered patio is presented with a round table and four chairs, surrounded by flower pots. The space is enclosed by brick walls, with multiple large windows providing natural light. A well-maintained lawn offers a peaceful outdoor environment.

Home in Lawrenceburg

Comfort in the Bluegrass

4.97 out of 5 average rating, 110 reviews

The exterior of the home features brick siding with white trim and dark blue shutters. Lush green grass surrounds the property, complemented by mature trees. A set of steps leads to the front door, which is framed by small hedges on either side.

Home in La Grange

The Squirrel's Nest - 3 bed/2 bath with hot tub

4.99 out of 5 average rating, 210 reviews

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.

Home in Louisville

Newly Renovated Derby House

The exterior of the home features a welcoming porch with rocking chairs framed by neatly trimmed hedges. A manicured lawn with shrubs enhances the inviting approach to the entrance. Surrounding trees provide a natural backdrop, contributing to the overall charm of the property.

4.93 out of 5 average rating, 251 reviews

Wilkinson's Wheated Oasis/ 1.3 Mi to Buffalo Trace

4.96 out of 5 average rating, 232 reviews

A cozy living area features a large sectional sofa and a colorful area rug. Natural light enters through two windows, illuminating the room. A ceiling fan enhances airflow, and decorative elements include a shelf with framed artwork.

Home in La Grange

Little Blue Cottage on Main Street, La Grange KY

5.0 out of 5 average rating, 129 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

Condo rentals with a patio

4.96 out of 5 average rating, 270 reviews

A stylish living area features a warm, orange-brown sofa and a black armchair, complemented by a vibrant area rug. Exposed brick walls and modern cabinetry create a cozy yet contemporary vibe. Natural light fills the space, filtered through dark curtains.

Condo in Jeffersonville

The Greatest penthouse in the heart of city

Condo in Central Business District

The rooftop patio features a relaxing seating area with wicker furniture, including a couch and a stylish hanging chair. A coffee table sits in the center, complemented by potted greenery. The space is surrounded by a decorative railing and offers an inviting atmosphere for outdoor enjoyment.

4.95 out of 5 average rating, 140 reviews

Downtown Penthouse Loft- Free Parking & Elevator

Superhost

A living area showcases a combination of modern and rustic elements. A leather sofa faces a brick wall with a decorative sign. A vibrant area rug adds color, while a blue armchair and a wooden coffee table provide seating and surface space. A breakfast bar is visible in the background.

Condo in Louisville

4.8 out of 5 average rating, 121 reviews

Nulu/Butchertown 2 BR, along urban bourbon trail

4.88 out of 5 average rating, 68 reviews

The living room features a light-colored sofa and armchair, complemented by wooden side tables. A large wall-mounted TV and a ceiling fan are visible, along with a plush area rug. Natural light comes from the door leading to an outdoor space.

Condo in Crestwood

Luxury Apartment/Near Louisville/EV Charger

4.98 out of 5 average rating, 61 reviews

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.

Condo in Louisville

Cherokee Park / Highlands Charm

4.91 out of 5 average rating, 46 reviews

The panoramic view showcases the illuminated Louisville skyline at night, reflecting in the water below. Various colored lights from buildings create a vibrant display against the dark sky, while the bridge structure adds depth to the scene.

Condo in Jeffersonville

BEST View of Louisville

Condo in Central Business District

A spacious living area is highlighted by original exposed brick walls and large windows that allow natural light to fill the space. A round wooden dining table is surrounded by six chairs. Comfortable seating is arranged nearby, complemented by modern lighting fixtures.

5.0 out of 5 average rating, 41 reviews

Corner Penthouse at the Historic Levy Building