Holiday rentals with outdoor seating in Shepherdsville

4.98 out of 5 average rating, 233 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)

4.99 out of 5 average rating, 102 reviews

Home in Springfield

Bourbon Trail + Events + Hot Tub +Walk 2 Dine

Charming, spotless, and historic yet modern, a few words from 5-star reviews! The Kentucky Barrel House a unique retreat on the Bourbon Trail. Take a dip in the hot tub- grab a towel from the warmer, chat by the firepit. Pet-friendly, fenced yard. Equipped kitchen, or walk to downtown restaurants. Minutes to: Maker’s Mark, Willett, Bardstown Bourbon, Heaven Hill, Beam and many more. Near Cornerstone Acres Events, The Grove At Silverton Hill, My Old Kentucky Home. Celebrate National Bourbon Week!

4.9 out of 5 average rating, 112 reviews

An outdoor living space features a hot tub beneath a wooden pergola, with water cascading gently. Comfortable seating is arranged nearby, facing a cozy firepit. Bright orange doors lead to the interior, surrounded by lush greenery and a privacy fence.

Home in Coxs Creek

The Barrel Proof Bungalow

This stylish 3 bedroom 2 bathroom home on the "Kentucky Bourbon Trail" has been a labor of love and full remodel down to the studs. The Barrel Strength Bungalow is centrally located between Interstate 65 (Jim Beam) and Bardstown's city center. A unique outdoor living space with one of a few hot tubs in Bardstown area Airbnb's. Also offers a firepit, outdoor grill and patio area. More than 15 distilleries within an hour's drive and approximately 30-35m to Downtown Louisville and Churchill Downs.

4.97 out of 5 average rating, 103 reviews

Cabin in Shepherdsville

Bourbon Cabin - Speakeasy/HotTub/Arcade/Derby

🏡 Bourbon Trail Hideaway – A spacious 5BR, 3.5BA log cabin on 6 private acres, just 9 mins from Jim Beam! 🍂 Blending rustic charm with modern comforts, this retreat features a Brand NEW speakeasy lounge, hot tub, fire pit, wraparound decks, arcade games, and a well-stocked kitchen. Enjoy breathtaking sunsets, fast WiFi, plush seating, Smart TVs, and a cozy ambiance, plus luxurious beds, spa-like bath, and plenty of space to relax or entertain. Perfect for groups, couples & bourbon lovers! 🥃✨

Place to stay in Vine Grove

A cozy bedroom features a spacious bed with crisp white linens and decorative pillows. Above the bed, a vibrant artwork of a cow adds a touch of character to the room. A bedside lamp and a small blue nightstand provide additional comfort.

4.99 out of 5 average rating, 166 reviews

Fort 5400

Rustic 1 bedroom unit on 6 acres. Beautiful creek a couple hundred yards from your door with lovely sunsets. Vaulted living room, dual reclining sofa, 50 inch ROKU TV & dinette. Kitchenette with full size refrigerator, microwave, and Keurig coffee maker. King size bed, cozy electric fireplace, 32 inch ROKU TV and closet with washer/dryer. The grounds are shared with one other tenant. FT Knox-6.2 Miles Elizabethtown Sports Park-15 miles Church Hill Downs-36 miles Boundary Oak Distillary-7 miles

Superhost

A cozy living area is highlighted by a large, plush bean bag chair and a comfortable sofa. A wall-mounted TV is positioned near a small table. Light-colored walls contrast with the dark furniture, while natural light enters from a nearby doorway.

Townhouse in Elizabethtown

4.98 out of 5 average rating, 275 reviews

Bear-BnB - Relaxing Bear Themed Space

You will be close to everything in Elizabethtown when you stay at this newly remodeled, centrally-located place with a Bear theme. Unique amenities unlike any experience Including: 1Gb Fiber with WiFi, 55" QLED TV, Nest Thermostat with Smoke & Carbon Monoxide, LoveSac Sactional with LoveSac SuperSac coined the ":Bear Chair", Keurig D-Duo Coffee, premium Therapeutic brand mattresses. Full Laundry, and Flywheel Exercise Bikes, Weber Natural Gas Grill and Outdoor Seating area. Included Laundry

4.98 out of 5 average rating, 290 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.

Farm stay in Elizabethtown

4.99 out of 5 average rating, 144 reviews

Mini Cow Cottage! Peaceful Farm Getaway

Come enjoy this peaceful private getaway in a beautiful country setting that is still close to town and the bourbon trail. The cottage offers two bedrooms (one king, one queen) and one bath with an open floor plan, fully stocked kitchen, W/D, front and back covered porches, and don't forget the animals! We have mini Highland cattle, a horse, 3 very friendly barn cats, and spacious natural surroundings. There is also a walking trail along the woods, and a beautiful pond. Dogs welcome too!

4.89 out of 5 average rating, 217 reviews

A single-story brick home is featured, surrounded by well-maintained landscaping. A paved driveway leads to a two-car garage, and a basketball hoop is positioned on the right. The yard offers a grassy area with neatly trimmed bushes and trees providing light shade.

Home in Louisville

Lilly's Pad

Relax and unwind in between all your Louisville activities. We are close (4.4miles) from SDF airport ,and I65 and the Gene Snyder Freeway are less than 8miles away. There are a plethora of activities from shopping to entertainment venues such as horse racing at historic Churchill Downs, Louisville Zoo, Kentucky Kingdom amusement park, Muhammad Ali museum and childhood home, Louisville Slugger Museum, Valhalla golf club, and 36 Bourbon Distilleries as well as cave exploring and fishing.

Place to stay in Shepherdsville

A spacious sleeping area features a king bed with a soft beige quilt and matching pillows. Two bedside lamps provide warm lighting beside wooden nightstands. The ceiling is accented by textured panels, and the cozy carpet extends across the floor.

4.89 out of 5 average rating, 342 reviews

A Little Bit of Kentucky

A unique loft apartment near Louisville, Bardstown and just across the river from Indiana. This is attached to our Wedding venue for the convenience of anyone who is coming in for a wedding. It has its on separate entrance away from the venue so you wont be bothered by anyone. We are more than willing to accommodate you in any way we can. Let us know what you need and we will do our best to meet your needs. Check our guide book for local attractions and mileage

Guest suite in Coxs Creek

A cozy living area is furnished with a spacious sectional couch and a leather armchair. A wooden coffee table holds magazines. Light-colored walls are complemented by framed artwork, and a pass-through window connects to the kitchenette area.

4.99 out of 5 average rating, 228 reviews

★Jenny's Place - Basement Suite, Private Entrance★

Welcome to Kentucky & Bourbon Country! Jenny's Place includes your own private lower-level walkout suite, with all the amenities, nestled in a quiet subdivision. We are centrally located near many events and activities, including the Bourbon Trail, Four Roses Bottling (5 min away), Jim Beam Distillery (10 min away) and Bernheim Forest (10 min away). We are conveniently located 15 minutes from Bardstown, the Most Beautiful Small Town in America. Come see us!

4.96 out of 5 average rating, 160 reviews

The cottage is nestled among lush greenery, showcasing a unique design with corrugated metal and concrete. A wooden deck leads to the entrance, surrounded by neatly arranged flower beds. Windows provide ample natural light while blending harmoniously with the woodland surroundings.

Cottage in Coxs Creek

Bourbon Way Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS

Popular amenities for outdoor seating rentals in Shepherdsville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.91 out of 5 average rating, 183 reviews

A spacious living area displays a mix of comfortable seating options, including a sofa, armchair, and patterned rug. A vibrant mural above the fireplace adds a pop of color. The adjoining kitchen is visible in the background, enhancing the open layout of the space.

Home in Shelby Park

Colonel Lou Lou's

4.98 out of 5 average rating, 128 reviews

A spacious living area features a comfortable gray sofa, wooden coffee table, and two stylish chairs. A wall-mounted television is visible, complemented by decorative shelves. Natural light enters through windows, while recessed lighting enhances the modern ambiance. The hardwood look flooring adds warmth to the space.

Home in Elizabethtown

✸ Bright, Modern 3BR | Etown Sports Park 1.8 mi✸

4.91 out of 5 average rating, 323 reviews

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.

Home in Clifton Heights

Quiet Neighborhood Home With Outstanding Location

Superhost

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

4.98 out of 5 average rating, 137 reviews

Walking Bridge, Putt Putt House

4.96 out of 5 average rating, 163 reviews

An outdoor fire pit surrounded by light blue chairs is situated in a green backyard, offering a welcoming space for gatherings. Trees and soft grass create a tranquil environment, enhanced by evening lighting.

Home in Louisville

Near Expo • Churchill Downs • Downtown • Cozy

5 out of 5 average rating, 114 reviews

A spacious living room showcases a sectional sofa adorned with yellow accent pillows. A wooden coffee table sits atop a striped rug, while a mounted TV and an electric fireplace provide modern comforts. Natural light enters through the large windows, enhancing the inviting atmosphere.

Home in Bardstown

Bluegrass and Bourbon - Peace on the Bourbon Trail

4.99 out of 5 average rating, 202 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

4.98 out of 5 average rating, 138 reviews

The exterior of the home features a charming white façade with black accents, complemented by a small set of steps leading to the front door. Lush green grass surrounds the property, and a gravel pathway is lined with decorative stones and small shrubs.

Home in Springfield

Bourbon Trail Schoolhouse

Apartment rentals with outdoor seating

A spacious living area is equipped with a comfortable sectional sofa and accent chairs arranged around a decorative area rug. A flat-screen TV is mounted above a cozy fireplace, with natural light streaming through large windows. A small nook offers a seating space for relaxation.

4.93 out of 5 average rating, 122 reviews

Cozy Bardstown Rd Apt | W/D, Fast WiFi, Parking

4.99 out of 5 average rating, 122 reviews

A comfortable living area features a soft beige couch and a matching armchair positioned around a dark wood coffee table. A plush area rug enhances the warmth of the wood flooring. A workspace with a desk and lighting can be seen in the background.

Flat in Radcliff

Blue Moose Studio 7 miles from KNOX, 9 to E-town

A charming duplex is depicted with a well-maintained lawn featuring vibrant greenery and flowers. Two entrance doors are visible, flanked by large windows that allow natural light. A gentle slope leads up to the property, enhancing its inviting presence.

4.94 out of 5 average rating, 355 reviews

Lucky Horseshoe

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.

4.94 out of 5 average rating, 732 reviews

Charming Highlands apartment

4.92 out of 5 average rating, 194 reviews

The modern kitchen features dark cabinetry, a spacious island with a double sink, and a tray containing snacks. Ambient lighting is provided by hanging pendant fixtures. Stainless steel appliances, including a microwave and refrigerator, enhance the contemporary design, while the open layout connects to the living area.

Flat in Corydon

Deuward’s Den - In Historic Corydon, IN

Flat 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, 191 reviews

Falls City Loft - Free parking!

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.

4.98 out of 5 average rating, 162 reviews

Haus on Speed, charming 2nd floor apartment

Flat 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, 186 reviews

An Unhurried Stay in Butchertown · Steps from NuLu

Apartment rentals with outdoor seating

4.83 out of 5 average rating, 153 reviews

A unique wooden chair with a flowing design is positioned against a white wall, featuring a mounted longhorn skull above it. The space is highlighted by dark wooden beams and flooring, creating a contrasting visual effect.

Apartment in Louisville

Cherokee Park Hideaway

Apartment 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.

4.98 out of 5 average rating, 50 reviews

Cherokee Park / Highlands Charm

Apartment in Crescent Hill

A two-story brick duplex is seen with white window trim and dark shutters. Lush green grass surrounds the property, complemented by neatly arranged rocks and low shrubs. The front door is accessible via a short set of steps, highlighted by sunlight filtering through nearby trees.

4.96 out of 5 average rating, 161 reviews

Hidden GEM, newly furnished in a safe, great area

Apartment in Saint Matthews

A spacious, walk-in shower is enclosed in glass, showcasing stylish Carrara marble walls and a built-in bench. Multiple shower fixtures, including an overhead showerhead, are visible. A plush gray towel is hung neatly on a glass panel, enhancing the modern and elegant design.

4.96 out of 5 average rating, 286 reviews

The Sweet Spot! - Live Like a Local

Apartment in East Market District

A colorful mural featuring vibrant horses adorns the exterior wall of the NULU Marketplace. The artwork is complemented by geometric shapes and bright colors, adding visual interest to the building's facade. Small trees and landscaping enhance the inviting atmosphere of the marketplace.

4.96 out of 5 average rating, 144 reviews

The Old Fashioned~Luxury 1BR~Stay Nulu Marketplace

Apartment in Elizabethtown

A modern townhouse features a two-story brick exterior with arched columns and large windows. A covered deck extends from the second floor, providing outdoor seating. A wrought-iron railing surrounds the deck, while access is available via a short ramp leading to the entrance.

4.99 out of 5 average rating, 139 reviews

“New” Downtown Modern Luxury Townhouse!

Apartment in Central Business District

An open living area features exposed brick walls and hardwood flooring, enhanced by natural light from large windows. A spacious leather couch is complemented by a wooden coffee table and two ceiling fans. The kitchen showcases a granite island and modern appliances.

4.9 out of 5 average rating, 278 reviews

Downtown Condo | Private 1 CAR Garage & Balcony