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, 387 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.

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, 378 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.

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

Home in Historic Western Suburb

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!

Townhouse in North Limestone

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.

4.98 out of 5 average rating, 298 reviews

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, 719 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**

Apartment in North Limestone

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

4.95 out of 5 average rating, 257 reviews

A spacious bedroom features a comfortable bed with plush linens, complemented by a decorative area rug. Natural light enters through two windows, illuminating the room. An air conditioning unit is mounted on the wall, and a stylish lamp stands beside the bed.

Apartment in Lexington

Location! Beautiful Downtown Apt, Across from Rupp

Beautiful, fully renovated (2021) apt in a historic building on Spring Street--as close as you can be to Rupp Arena and the Convention Center. PARKING IS AVAIL. You can walk to everything! Coffee shops, restaurants/bars & anywhere in downtown Lexington! Extra spacious & outfitted with comfortable furnishings, plush linens, basic kitchen amenities & new appliances. The home includes WIFI and two ROKU Smart TVs. Enjoy your morning coffee from the comfort of your large, private porch.

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, 232 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

5 out of 5 average rating, 128 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 spacious bedroom features a large bed with neutral-toned bedding, flanked by two wooden nightstands with table lamps. Natural light filters through two windows, and an abstract painting is displayed above the bed, adding a touch of color to the serene space.

4.92 out of 5 average rating, 207 reviews

Bright Cozy Stay| Fenced Yard| Near I-75 Horsepark

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

4.97 out of 5 average rating, 154 reviews

A spacious backyard is shown, featuring well-maintained green grass and tall trees providing shade. A hot tub and outdoor dining area are placed next to the house. A colorful playground is visible in the background, adding to the inviting atmosphere of the outdoor retreat.

Home in Georgetown

Luxe Hot Tub + Playground | Near KY Horse Park

4.95 out of 5 average rating, 118 reviews

An open-concept living area features high ceilings supported by dark beams. A comfortable sofa and a rug are positioned on the wood floor, while a kitchen with colorful bar stools is visible in the background. Large windows allow natural light to fill the space.

Home in Georgetown

Modern Farmhouse/20 acres/9 miles from Horse Park

A single-story home is shown, featuring a wooden ramp leading to the front entrance. The exterior is painted in light colors, complemented by dark window shutters. Lush green grass surrounds the property, and a tree with red leaves is visible nearby, adding color to the scene.

4.88 out of 5 average rating, 238 reviews

Liggett Lounge: Great location for ALL occasions

4.9 out of 5 average rating, 153 reviews

Keenland Special - 1 Mi to UK & Downtown & Rupp

4.94 out of 5 average rating, 228 reviews

Spacious King Suite | Horses, Fire Pit, Garage

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

4.81 out of 5 average rating, 101 reviews

The spacious living area features elegant furnishings, including a dark sectional sofa and a patterned armchair. A plush ottoman sits in the center, with a decorative tray placed atop. Large windows allow natural light to fill the room, highlighting the hardwood floors and original architectural details.

Apartment in Georgetown

Secretariat @The HoM- KY Horse Park, Ark, Downtown

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

4.86 out of 5 average rating, 222 reviews

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.

Apartment in Lexington

*Luxury One Bedroom Apt| Downtown Lexington*

4.92 out of 5 average rating, 114 reviews

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.

Apartment in Lexington

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

Apartment in North Limestone

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

Condo in Historic Western Suburb

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.

4.98 out of 5 average rating, 58 reviews

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, 163 reviews

Bourbon Trail R&R

Condo in Historic South Hill

Rye'd Away Unit 505

Condo in Historic Western Suburb

4.94 out of 5 average rating, 164 reviews

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.