Holiday rentals with outdoor seating in Versailles

4.99 out of 5 average rating, 192 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)

4.98 out of 5 average rating, 276 reviews

A porch overlooks the serene Kentucky River, featuring a wood breakfast bar with counter stools. Rocking chairs provide a cozy seating area, framed by lush greenery and views of the river's banks. Sunlight filters through the trees, enhancing the tranquil setting.

Cottage in Wilmore

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

5 out of 5 average rating, 111 reviews

Cabin in Frankfort

Bourbon Trail log Cabin! Hot tub~hiking~game shed!

🌲FOR CHRISTMAS- home is transformed into cozy holiday cabin retreat! 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 plenty of fun 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!

5 out of 5 average rating, 114 reviews

The home is nestled amidst a backdrop of gently rolling hills, framed by trees showcasing autumn foliage. A welcoming front porch is visible, accompanied by a small staircase leading to the entrance. Large windows allow natural light to filter into the living space.

Home in Versailles

Birdsong Valley on Bourbon Trail

Great central location on Bourbon Trail. Close to Lexington, airport, Keeneland, Ride the Rails, Horse Park, Shakertown, many other attractions. You will love our 3 bedroom charming home on 2.2 beautiful acres in peaceful community. Perfect for couples, friends, families, singles to explore distilleries, horse farms, quaint small towns of Versailles, Midway, Lawrenceburg, country backroads, much more. OR relax, enjoy nature, butterflies, birds, deer. Let us make lodging highlight of your visit.

Guesthouse in Nicholasville

Lush green grass frames the scene, with two flowering trees prominently in the foreground. A wooden fence lines the area, leading to a cottage that is partially obscured by the trees. Natural light brightens the surroundings on a clear day.

4.98 out of 5 average rating, 369 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Townhouse in Meadowthrope

The living room is showcased, featuring a comfortable full-size sofa and two armchairs. The walls are adorned with framed artwork, and a coffee table sits in the center. Soft lighting creates a welcoming atmosphere, complemented by colorful area rugs underfoot.

4.88 out of 5 average rating, 505 reviews

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

4.98 out of 5 average rating, 466 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!

4.97 out of 5 average rating, 702 reviews

The entrance to the historic Buffalo Springs Distilling Company is showcased, featuring sturdy stonework and a wooden door. A sign hangs above the entrance, indicating the building's name. Nearby, green grass is visible, hinting at the surrounding area.

Home in Stamping Ground

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

4.94 out of 5 average rating, 302 reviews

A spacious glamping tent is set among vibrant greenery, featuring a conical roof and large entrance. Natural light filters through the trees, casting soft shadows on the wooden deck. The scene captures a peaceful ambiance, inviting guests to relax in nature.

Treehouse in Georgetown

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

4.98 out of 5 average rating, 197 reviews

A well-equipped kitchen features a spacious wood island with two upholstered stools. Modern appliances, including a gas range and sleek cabinetry, complement the space. Natural light streams through the windows, enhancing the inviting atmosphere, while tasteful decor adds a touch of character.

Loft in Frankfort

The Loft - Cozy Retreat in Historic Downtown

Experience the warmth and charm of The Loft your top-rated fall retreat just 8 minutes from downtown. Stroll to the Capitol, see the autumn sights, and take in Horse Country nearby. Snuggle into a cozy bed, curl up on the couch, and enjoy modern touches in your private second-floor hideaway. With parking at the door and a hygge-inspired vibe, it’s perfect for crisp days and cozy nights. Just minutes from 13 distilleries, The Loft is your ideal base for a stylish Bourbon Trail escape.

4.95 out of 5 average rating, 219 reviews

A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.

Home in Versailles

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

4.98 out of 5 average rating, 132 reviews

A well-maintained backyard area is highlighted by a green hammock suspended between trees. The brick apartment is elevated with a wooden deck and stairs leading to the entrance. Surrounding the space, manicured shrubs and grass create a peaceful outdoor environment.

Guesthouse in Frankfort

Treetop Hideaway

Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

Popular amenities for Versailles outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

Superhost

A charming backyard features a spacious patio area with a BBQ grill and seating under a sunshade. Lush green grass surrounds the patio, enhancing the outdoor setting. The home is painted in a deep blue, complemented by a colorful sunset creating a serene backdrop.

Home in Lawrenceburg

4.83 out of 5 average rating, 109 reviews

Bourbon Trail/8 mins to distilleries/Fenced Yard

4.93 out of 5 average rating, 289 reviews

A spacious bedroom features a comfortable bed dressed in soft bedding. Natural light is provided by a window, and a ceiling fan offers airflow. A wooden dresser and two nightstands add functionality, while tasteful decor pieces enhance the inviting ambiance.

Home in Nicholasville

Cali King beds w/ Koi pond Oasis. 15 min from LEX

4.98 out of 5 average rating, 243 reviews

A charming two-story house features a blue exterior with stone accents and a welcoming front porch. Green grass and well-maintained landscaping frame the walkway, while blooming flowers add a touch of color. The home is situated in a peaceful neighborhood.

Home in Frankfort

Blue’s Bourbon Bungalow

4.99 out of 5 average rating, 167 reviews

A living area features a dark leather sectional sofa and a patterned accent chair, providing ample seating options. A low coffee table sits on a colorful area rug, while natural light fills the space through nearby windows. A door leads to the exterior.

Home in Lexington

Horse Central-Be our Guest!

4.89 out of 5 average rating, 209 reviews

A spacious living area features a comfortable grey sofa and armchairs arranged around a white coffee table. Light-colored curtains frame large windows, while a dining area with a dark wood table is visible in the background, alongside a modern kitchen with stainless steel appliances.

Home in Lexington

Perfect for Traveling Professionals & Vacation!

4.97 out of 5 average rating, 153 reviews

A bright living area features a light-colored sofa and two beige armchairs arranged around a glass coffee table. Natural light enters through two large windows, complemented by white curtains. A green front door adds a pop of color to the welcoming space.

Home in Kenwick

The Rosewood Cottage of Lexington I Elegant & Cozy

5 out of 5 average rating, 106 reviews

A dining area features a round wooden table set with glassware and green accents. A striking mural of bourbon barrels lines one wall, illuminated by a modern pendant light, while a doorway leads to other spaces in the home.

Home in Frankfort

*Long Pour: Your Luxury Downtown Bourbon Home*

4.91 out of 5 average rating, 191 reviews

Home in Lexington

Cottage w/Jacuzzi - centrally located, comfy beds!

Apartment rentals with outdoor seating

4.84 out of 5 average rating, 148 reviews

A spacious living area features a dark sectional sofa and a round coffee table set on a decorative area rug. Natural light floods through the large bay windows with white drapes, illuminating the contrasting hardwood flooring and the cozy dining set nearby.

Apartment in Georgetown

Man O'War @ The HoM- KY Horse Park, Ark, Historic

4.98 out of 5 average rating, 212 reviews

A spacious living area features a light-colored sofa accompanied by decorative orange cushions. A coffee table with a woven texture sits on a textured area rug. Large sliding doors open to the patio, framed by a vibrant mural and greenery, enhancing the natural light.

Apartment in Lexington

"Uptown Retreat" - Cozy Fireplace & Sauna

5 out of 5 average rating, 137 reviews

A vibrant seating area features a plush red sofa adorned with decorative pillows. A light marble side table sits nearby, complemented by an intricate metal screen and lush greenery. Warm lighting from hanging fixtures enhances the inviting atmosphere of the space.

Apartment in Lexington

Swanky Boho - Downtown

Apartment in Meadowthrope

A cozy living area features a striped sofa and two armchairs, creating a comfortable seating arrangement. Two lamps provide soft lighting, while a wooden side table holds a small plant. The hardwood floor is complemented by a large area rug, enhancing the warm atmosphere.

4.95 out of 5 average rating, 156 reviews

Nonie's Abode

4.86 out of 5 average rating, 354 reviews

A well-appointed bedroom features a spacious bed dressed in white linens and an array of decorative pillows. Natural light filters through sheer curtains, illuminating the room. Two bedside lamps provide additional lighting, and a wall art piece adds a touch of elegance.

Apartment in Frankfort

The Grey Lady- 300YD from BT Distillery

Apartment in Woodward Heights

The living area features a comfortable gray sofa paired with two orange accent chairs. A dark coffee table sits in front, complemented by a large, colorful artwork on the wall. A flat-screen TV is positioned on a wooden stand, with plants adding a natural touch.

4.98 out of 5 average rating, 342 reviews

Downtown Apartment in Victorian Home

4.94 out of 5 average rating, 141 reviews

The cozy living area features a comfortable recliner chair and a plush sofa, complemented by a decorative area rug. A dining table for two is positioned near the window, illuminating the space with natural light. The room is styled with artwork and a TV stand.

Apartment in Richmond

Simply sweet - Entire 1 bed upstairs apt near EKU

4.96 out of 5 average rating, 388 reviews

A spacious living area features a neutral-colored sofa with decorative pillows, paired with a wooden coffee table. Art pieces adorn the walls, and a ceiling fan circulates air. A large window allows natural light to fill the room, highlighting the hardwood flooring.

Apartment in Richmond

Luxury on Main / East

Condo rentals with outdoor seating

Condo in Historic South Hill

An open living area features wooden ceilings, large windows dressed with patterned curtains, and stylish seating options. A mix of modern and vintage furniture creates a cozy space, complemented by decorative rugs and a dining area adorned with a chandelier.

5 out of 5 average rating, 20 reviews

The Big Blue Wave - 2-Bedroom Condo by Rupp Arena

An open living area features large glass doors that provide views of the greenery outside. Industrial elements, such as exposed beams and metal accents, complement a cozy seating arrangement with a sectional sofa and wooden coffee table. A dining table with bar stools is visible in the background.

4.95 out of 5 average rating, 239 reviews

Top Shelf the only Airbnb in KY above a Distillery

4.94 out of 5 average rating, 160 reviews

A living area features two dark couches adorned with decorative pillows, situated around a wooden coffee table. Soft lighting is provided by two table lamps. A small desk with an office chair is positioned in the corner, while a patterned rug anchors the space.

Condo in Frankfort

Bourbon Trail R&R

4.88 out of 5 average rating, 136 reviews

The exterior of the condo is displayed, featuring a brick facade and a welcoming green door under a gabled roof. Two windows flanking the door allow natural light, and a small pathway leads to the entrance, complemented by neatly maintained greenery.

Condo in Shelbyville

Work, Family and Friends and Bourbon

4.93 out of 5 average rating, 150 reviews

Graffiti Art Haus - Walk to Central Bank Arena

A sitting area features a gray couch, a secretary's desk with a padded chair, and a flat-screen TV mounted on the wall. An artwork titled 'The Nude' hangs beside a window, allowing natural light to fill the space. Antique hardwood floors are visible.

4.95 out of 5 average rating, 56 reviews

Federico's Historic Studio - Downtown

A light-colored sofa is adorned with decorative navy and yellow pillows, positioned in a bright living area. A yellow throw blanket is casually draped over one armrest. The background includes a kitchenette and large windows allowing natural light to fill the space.

Condo in Frankfort

4.63 out of 5 average rating, 192 reviews

Capital City Condo #8

A cozy corner is highlighted by a vintage poster of 'The Queen's Gambit' by Walter Tevis. A wooden table features a chessboard, while a textured gray chair is positioned nearby, complemented by two elegant lamps casting a soft light. A patterned curtain adds visual interest.