Vacation rentals with outdoor seating in Shepherdsville

4.99 out of 5 average rating, 104 reviews

Home in Springfield

Private Hot Tub + Bourbon + Fire Pit | Itinerary

Hot tub, Fire pit , Bourbon Trail Location, 10 Miles from Maker’s Mark and many more distilleries. Boutique style. Customized Complimentary Itinerary , Walkable restaurants, Fenced dog yard. The Kentucky Barrel House a unique retreat on the Bourbon Trail. Equipped kitchen, 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 KY Home. Fast WIFI, Fireplace (electric)

4.91 out of 5 average rating, 116 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, 109 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, 169 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

Townhouse in Elizabethtown

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.

4.98 out of 5 average rating, 281 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, 299 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.

5 out of 5 average rating, 116 reviews

A serene outdoor space is illuminated by string lights, creating a warm ambiance at night. Adirondack chairs surround a circular fire pit, with a charcoal grill nearby, set against a backdrop of greenery. The screened-in porch can be seen in the background.

Home in Bardstown

Bluegrass and Bourbon - Peace on the Bourbon Trail

Retreat to your peaceful hangout after a day of exploring all that Bardstown and KY have to offer! Relax by the fireplace and stream a movie on the 75" TV, cook a full meal in the well-stocked kitchen, create a unique cocktail with all the tools you could wish for, breathe fresh air on the screened-in porch that borders greenspace, challenge friends to poker in the game room, grill dinner on our charcoal grill, or roast hot dogs and s'mores on the firepit area. This must be the place.

Guest suite in Shepherdsville

The outdoor space features a concrete patio surrounded by colorful trees, showcasing a blend of autumn hues. A charcoal and gas grill is covered, positioned on one side of the patio. The entrance door to the lower-level unit is visible, offering a private and secure access point.

4.99 out of 5 average rating, 101 reviews

Private 1000 sq ft 1-bedroom lower level apartment

Relax in this beautiful wooded setting in Bourbon Country less than 4 miles from I-65. Private entrance into freshly painted 1-bedroom unit with new kitchen and 9' ceilings. Perfectly located near 19 Bourbon Distilleries, 4 Wineries, Bernheim Forest, Knob Creek Gun Range, Churchill Downs and other exciting destinations. Jim Beam Distillery & Forest Edge Winery are 7 min away. There is a seasonal (shared) concrete patio, deck and pool available in the warmer months.

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, 344 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.

4.98 out of 5 average rating, 229 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, 162 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

4.98 out of 5 average rating, 241 reviews

Dome in Mount Washington

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Popular amenities for Shepherdsville outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.86 out of 5 average rating, 199 reviews

A charming home is shown with a light-colored exterior, framed by dark shutters and manicured shrubs. A concrete path leads to the welcoming red front door. Lush greenery and flower beds enhance the outdoor space, complemented by a peaceful sky.

Home in Simpsonville

Charming 4 Bedroom classic home bourbon trail!

4.96 out of 5 average rating, 132 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✸

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, 328 reviews

Quiet Neighborhood Home With Outstanding Location

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, 244 reviews

"Call Me Old-Fashioned"in Derby & Bourbon Country!

4.98 out of 5 average rating, 154 reviews

The cabin is elevated on stilts, surrounded by trees, and features a wraparound screened-in porch. A wooden deck leads to the entrance, where a flag hangs proudly. Gravel pathways converge near outdoor seating areas with picnic tables, providing a welcoming outdoor space.

Home in Elizabeth

Cabin on Lake Close to Louisville Ky

A welcoming front porch features a decorative bench beside a wooden barrel. A planter with colorful flowers adds charm, while lush flowering plants provide a natural backdrop. Light filters through the greenery, creating a serene outdoor seating area.

4.94 out of 5 average rating, 140 reviews

Derby City Bourbon Bungalow - by Germantown & UofL

4.99 out of 5 average rating, 227 reviews

A light-filled dining area features a wooden table surrounded by white chairs. A blue area rug anchors the space, complemented by a chandelier above. A kitchen bar with seating is visible in the background, and large windows provide views of the surrounding trees.

Home in Bedford

Atoka Farms

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, 204 reviews

Newly Renovated Derby House

Apartment rentals with outdoor seating

4.86 out of 5 average rating, 290 reviews

A spacious bed is positioned in the center of the room, dressed in neutral bedding with a light blue throw at the foot. Two bedside lamps flank the bed, and a set of three cityscape prints hangs above, complementing the cozy atmosphere.

Apartment in Louisville

The Nest

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.

Apartment in Radcliff

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

4.94 out of 5 average rating, 357 reviews

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.

Apartment in Louisville

Lucky Horseshoe

4.94 out of 5 average rating, 736 reviews

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.

Apartment in Louisville

Charming Highlands apartment

4.92 out of 5 average rating, 195 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.

Apartment in Corydon

Deuward’s Den - In Historic Corydon, IN

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, 195 reviews

Falls City Loft - Free parking!

Apartment in Jeffersonville

A cozy living area features a black leather sofa with decorative pillows and a single red armchair. Double doors open to a spacious deck with a river view. A glass coffee table sits on a patterned rug, with a TV mounted on the wall and a small console table nearby.

4.98 out of 5 average rating, 320 reviews

Renovated Riverfront Apartment with Elevated Deck

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, 187 reviews

An Unhurried Stay in Butchertown · Steps from NuLu

Condo rentals with outdoor seating

Condo in East Market District

A spacious living area features a large sectional sofa and a coffee table, set on a textured area rug. A flat-screen television is positioned on an elegant TV stand, with large windows allowing natural light to illuminate the space.

4.99 out of 5 average rating, 114 reviews

Walk to Bourbon Trail | NULU Gem | Gated Parking

5 out of 5 average rating, 29 reviews

A spacious living area features large windows with natural light, complemented by a blend of seating including a stylish armchair and a plush sofa. Elegant decor includes a decorative rug and a coffee table, creating an inviting space that opens to a private balcony.

Condo in Louisville

Luxe PLACE Apt in Lucky 13 Duplex w/ Free Parking

4.83 out of 5 average rating, 155 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.

Condo in Louisville

Cherokee Park Hideaway

4.96 out of 5 average rating, 163 reviews

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.

Condo in Louisville

Hidden GEM, newly furnished in a safe, great area

4.96 out of 5 average rating, 289 reviews

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.

Condo in Saint Matthews

The Sweet Spot! - Live Like a Local

Condo 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, 145 reviews

The Old Fashioned~Luxury 1BR~Stay Nulu Marketplace

4.99 out of 5 average rating, 141 reviews

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.

Condo in Elizabethtown

“New” Downtown Modern Luxury Townhouse!