Vacation rentals with outdoor seating in Lexington

A private entrance is framed by trees displaying vibrant autumn foliage, adding bursts of red and orange. A gravel driveway leads toward a gated entrance, while fallen leaves create a colorful carpet along the pathway. Clear blue skies provide a bright backdrop.

4.95 out of 5 average rating, 388 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

A stylish bedroom features a spacious bed with light grey bedding and a decorative throw. Natural light fills the room from multiple windows, complemented by a ceiling fan and wooden beams above. A small seating area and a blue dresser add functional elegance.

4.92 out of 5 average rating, 289 reviews

Sunset Over Lex-Downtown w Deck at Rupp Arena

Spacious, light-filled apartment across from Rupp Arena, walkable to downtown and UK's campus. The bedroom features a king sized Sealy mattress and plush bedding. Enjoy a gorgeous bathroom, full kitchen, and huge second level deck overlooking Rupp. Located in a historic building but newly renovated, top to bottom. Equipped for remote work or relaxation with high speed internet and a Smart TV. Pioneer Split Units for AC and Heat. Free parking for easy access to conventions, concerts, and games.

4.95 out of 5 average rating, 256 reviews

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.

Condo in Lexington

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

A spiral slide in vibrant burgundy extends from a wooden ceiling to the floor, creating a playful focal point in the space. Natural light filters through windows, illuminating the smooth wood flooring and surrounding area, which includes modern appliances and a stylish chair.

4.95 out of 5 average rating, 133 reviews

Maryland Luxury Downtown Manor

Our Maryland Manor was designed to be a true Home away from Home.. with an indoor Slide for extra Fun!! Grab coffee, sit in the sleeping porch and slide back down for a refill! A creative, historic oasis perfect for exploring downtown Lexington! Located Downtown, Minutes walk to Rupp, Dining, Galleries, Night Life and Next Door to the Apiary. Paired with Off Street Parking and a large backyard, this stylish place to stay is perfect for group trips. We can’t wait to welcome you to our Home!

4.98 out of 5 average rating, 298 reviews

A spacious living area features a comfortable sofa and a cozy chair, complemented by a geometric patterned rug. A coffee table sits in the center, with natural light illuminating the space. The open layout leads to a kitchen visible in the background, enhancing the inviting atmosphere.

Townhouse in Lexington

Explore Bourbon Trail ♥Downtown & Free Parking

#15066671-2 Two spacious bedrooms, each with its very own full on-suite bathroom – think of it as a double dose of hotel-style comfort for the price of one! Not only is our place a cozy haven, but it's also nestled within a vibrant neighborhood...a leisurely stroll away from over a dozen restaurants, bars, craft breweries, a lively farmers market, & the opera house. If you peek out the window, you'll catch a glimpse of the charming Transylvania University campus, which is just a block away.

4.98 out of 5 average rating, 471 reviews

Distillery District Diamond-pet friendly

This 1948 bungalow in an up-and-coming neighborhood has two bedrooms/one bath. This house has all the updates you could ask of modern living including internet access, TVs with Roku, and keyless entry. Each bedroom has blackout curtains, ceiling fan and bedside power station. The bath is fully stocked with essential personal care items. The fenced-in back yard has a deck and a fire pit. STR Reg #15075605-1. Maximum occupants 4-Guests are prohibited from allowing more than maximum occupancy

4.97 out of 5 average rating, 720 reviews

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.

4.88 out of 5 average rating, 251 reviews

A spacious living room is highlighted by a large chandelier and a classic fireplace. Elegant furniture includes a gray sofa and two armchairs surrounding a coffee table. Natural light streams through tall windows, and the rich area rug adds warmth to the inviting space.

Townhouse in Lexington

The Statesman / Walk to Rupp / Superb Deck

The Statesman, in the heart of Lexington, allows opportunity to experience the conveniences of downtown by foot. This 3-story (stairs only) historic townhouse has undergone a face lift, having spared no expense with high end finishing. Enjoy modern day conveniences while maintaining the old-world charm. **Located above a local bar Henry Clay's Public House; noise is a potential on the second-floor bedroom/living room (3rd floor is less disturbed) from the live music; no parties allowed**

5 out of 5 average rating, 121 reviews

The exterior of The Dew Drop In is framed by two large trees, showcasing a well-manicured lawn. The house, painted in light colors, is set back from the foreground, with a wraparound porch visible. A wooden fence outlines the property, enhancing the natural setting.

Farm stay in Midway

Saxony Farm - The Dew Drop In

Nestled in the heart of Kentucky's Bluegrass region, The Dew Drop In, (newly constructed in 2018) is located on Saxony Farm, a working Thoroughbred horse farm, family-owned and operated for over 50 years. More than just a place to rest your head, guests will experience a home-away-from-home location, & enjoy the peace and quiet of farm life, all within striking distance of downtown Lexington, KY's Bourbon Trail, locally-owned restaurants, shops and numerous family-friendly activities.

A custom California King wooden bed is featured within an immersive room, surrounded by dark hues and dramatic lighting. Adjacent is a unique chair and a traditional rug, enhancing the room's historical charm and fantasy theme.

4.98 out of 5 average rating, 542 reviews

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

4.92 out of 5 average rating, 289 reviews

Two outdoor bathtubs are positioned on a wooden deck, surrounded by trees and views of the creek. An Adirondack chair sits nearby, providing a space for relaxation while enjoying the natural surroundings.

Treehouse in Georgetown

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

4.94 out of 5 average rating, 233 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

Popular amenities for Lexington outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

The exterior of a charming ranch home is displayed, featuring a brick facade and a two-car garage. A well-maintained driveway leads to the entrance, framed by landscaping including shrubs and small flower beds. Sunlight brightens the scene with a clear blue sky above.

4.92 out of 5 average rating, 137 reviews

Lovely 3 Bdrm Home w/Free Parking Close to I-75

The exterior of the home features natural stone accents, complemented by brown shutters on the windows. A well-maintained lawn with shrubs and seasonal foliage enhances the inviting entry. A concrete driveway provides parking, while a wooden deck is visible at the side of the house.

4.99 out of 5 average rating, 123 reviews

Creekside cabin in city. King bed. Walk in shower

5 out of 5 average rating, 129 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

A modern kitchen features light-colored cabinetry and a granite countertop, equipped with stainless steel appliances. A window with soft yellow curtains allows natural light to brighten the space. Decorative tile backsplashes add a subtle touch, while a rug enhances the floor area.

4.9 out of 5 average rating, 658 reviews

KY & Bourbon & Horses, Oh My! Close to Keeneland

A charming brick home with a gabled roof is framed by lush green trees and landscaped garden beds. A stone pathway leads to the front porch, where two white chairs invite relaxation. The welcoming facade features multiple windows allowing natural light.

4.95 out of 5 average rating, 298 reviews

3BR-4 Beds-2BA close to UK/Chevy Chase/Downtown

An inviting exterior view showcases a modern building at dusk, featuring warm light from hanging fixtures. A raised planter with vibrant greenery adorns the front, complemented by a wooden railing along the entrance, with a paved sidewalk lined by trees.

4.88 out of 5 average rating, 309 reviews

IT WAS ALL A DREAM - Modern Luxury in downtown LEX

4.99 out of 5 average rating, 116 reviews

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.

Home in Frankfort

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

4.91 out of 5 average rating, 569 reviews

A living room is filled with natural light, featuring a mix of comfortable seating options, including a leather couch and a fabric sofa. A coffee table holds magazines, and a TV is positioned against a wall. Nearby bookshelves display books and decorative items.

Home in Castlewood

The Cottage @ Castlewood Park

Apartment rentals with outdoor seating

4.93 out of 5 average rating, 106 reviews

The entrance to the 4th Street Retreat features a welcoming sign and a green door framed by beige siding. Natural light brightens the space, which is complemented by a small porch area. A colorful doormat adds a friendly touch to the entryway.

Apartment in Danville

Welcome to 4th Street Retreat

4.85 out of 5 average rating, 150 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

4.89 out of 5 average rating, 179 reviews

A wooden railing overlooks a serene river, with trees lining the opposite bank. A cozy plaid blanket drapes over the railing, alongside a glass decanter and two glasses, capturing the golden hues of a sunset.

Apartment in Winchester

Riverview 2 … enjoy the view !

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, 162 reviews

Nonie's Abode

The kitchen features modern white cabinetry and stainless-steel appliances, including a microwave and refrigerator. A double sink is positioned beneath a wall art piece, and a small decorative plant adds a touch of greenery to the countertop. Light reflects off the surfaces, enhancing the clean look.

4.86 out of 5 average rating, 223 reviews

*Luxury One Bedroom Apt| Downtown Lexington*

An aerial view captures a two-story house with a dark roof and a white exterior, positioned next to a well-maintained lawn. A concrete driveway leads to the entrance, with paths of grass lining the edges. Surrounding buildings and greenery are also visible.

4.92 out of 5 average rating, 114 reviews

Victorian Apt Downtown Lexington

4.87 out of 5 average rating, 365 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

A charming blue house with a welcoming orange door features a covered front porch that is flanked by two supportive columns. A brick walkway leads through lush greenery and vibrant flowers, enhancing the inviting entrance to the home.

4.93 out of 5 average rating, 105 reviews

The Blue House & Gardens: Unit 1

Condo rentals with outdoor seating

4.98 out of 5 average rating, 58 reviews

A welcoming bedroom features a spacious bed layered with neutral and earthy-toned bedding. A round mirror reflects natural light from the window, enhancing the room's brightness. A comfortable chair and a sleek dresser are positioned beside the bed, while an area rug adds warmth to the hardwood floor.

Condo in Lexington

Historic Downtown Condo

A dark gray sofa with decorative pillows sits against a light wall. A round wall clock is positioned above the sofa, displaying an elegant design. A patterned area rug in muted tones lies beneath the furniture, complementing the overall decor.

4.75 out of 5 average rating, 121 reviews

Capital City Condo #2

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, 22 reviews

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

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.

4.93 out of 5 average rating, 164 reviews

Bourbon Trail R&R

Condo in Historic South Hill

Rye'd Away Unit 505

4.94 out of 5 average rating, 164 reviews

Condo in Lexington

Graffiti Art Haus - Walk to Central Bank Arena

A light gray sofa is positioned against a pale wall, featuring blue and patterned decorative pillows. A round wall clock above the sofa displays natural wood tones. A coffee table with a dark wood finish rests in front, accompanied by a woven basket and a small decorative item.

4.59 out of 5 average rating, 246 reviews

Capital City Condo #6

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.