House holiday rentals in Lexington

A modern kitchen features sleek dark cabinetry and stainless steel appliances, offering ample counter space. Natural light floods the room, highlighting the herringbone-patterned floor. A wooden dining table with white, upholstered chairs invites meals together, while decorative shelves accentuate the wall.

4.93 out of 5 average rating, 893 reviews

Updated 1910 charm! Walk to Rupp/near Keeneland!

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This renovated Victorian home in downtown Lexington is within walking distance of excellent dining, distilleries, and entertainment. Attend a concert/sporting event at nearby Rupp Arena (5 min walk), stroll through Gatton Park (2 min walk), view the horse races at Keeneland (10 min drive), tour the Alltech bourbon distillery around the block, or explore the offerings of downtown just outside your front door

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, 392 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 warm living area is highlighted by natural light from a front window. A cozy seating arrangement is set against a decorative fireplace. A wooden dining table stands nearby, with greenery and décor enhancing the space. A wooden ladder and plants add character to the room.

4.99 out of 5 average rating, 153 reviews

The Flower Pot

Welcome to The Flower Pot! Come and stay at our newly renovated mid century modern home complete with a record player collection and great natural sunlight. This location is a hidden gem in Lexington! HIGHLIGHTS: - One turn off main road for easy access to ALL attractions and necessities in Lexington - The Distillery District, Rupp Arena, Keeneland, Red Mile(Railbird Music Festival), UK Campus all approximately 10 MINUTES OR LESS - 1 King bed/ Two Queen Beds with smart TVs - New luxury bathroom

4.99 out of 5 average rating, 118 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

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

The living room features vaulted ceilings and an open layout. A sectional sofa and a reclining chair offer comfortable seating, while a coffee table sits centrally. Light hardwood flooring and soft wall decor contribute to a bright and airy ambiance. A large TV is mounted on a nearby wall.

4.99 out of 5 average rating, 144 reviews

Newly renovated upscale house with high ceilings

Get away and cozy in at this clean and comfortable two bed, two bath private home centrally located in a convenient, quiet neighborhood less than a five-minute walk to Kroger, restaurants, coffee, and a yoga studio. Easily accessible to Fayette Mall and UK by car. Fully equipped kitchen for cooking meals, reclining sofa for relaxing, 65" TV, books and games. One new Sealy king bed and a bunk bed with one double and two twin mattresses (one trundle). Washer and dryer available for your use.

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.

4.96 out of 5 average rating, 136 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, 483 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, 727 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.

A collage showcases various outdoor and indoor entertainment areas. A blue pool is surrounded by sun loungers. A hot tub is visible nearby. Inside, a game room features a pool table, air hockey, and arcade machine, highlighting multiple recreational options.

4.97 out of 5 average rating, 142 reviews

Central Lex Summer Pool Oasis: Hot Tub! Game Room!

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, the University of Kentucky, or just looking for a fun getaway, we have all the entertainment you need! Featuring a POOL, HOT-TUB, ARCADE, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary FULLY STOCKED coffee bar and take in the cozy sounds by our fire pit in the back yard!

4.95 out of 5 average rating, 239 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

A spacious outdoor area features a hot tub accompanied by two cozy lanterns on a patio beside a lush green lawn. Four adirondack chairs are arranged for relaxation, framed by the home's light-colored exterior and contrasting dark shutters.

4.95 out of 5 average rating, 352 reviews

Relaxing Hot Tub | S’mores Fire Pit | Garage

Stay in one of Lexington's most desirable neighborhoods: quiet, safe, & in a low-traffic cul-de-sac that's also close to everything! Create lasting memories with friends & family: - Make s’mores by the fire pit under the stars! - Relax in the hot tub after a long day of travel! - Fenced in yard! - Coffee Bar! Just minutes from favorite local restaurants, shopping, attractions, downtown events, & the interstate (I-75 or I-64). Registration #15076499dash1

A modern kitchen is equipped with stainless steel appliances and sleek countertops featuring a marble pattern. Bar stools provide seating at a breakfast bar, while a flat-screen television is mounted on the wall. Natural light illuminates the space, enhancing the open layout.

4.88 out of 5 average rating, 165 reviews

Luxurious 1-bedroom with free parking on premise

Historical home located in the heart of Lexington, Kentucky. Few minute walk to Woodland Park, Kroger, Starbucks, bars, and restaurants. Gas station right around the corner. A convenient 3 minute drive and you're in the middle of downtown Lexington. Rupp Arena (1 mi), Kroger Field (1.5 mi), Keeneland (7 mi), Kentucky Horse Park (10 mi), Buffalo Trace Distillery (26 mi). 1GB fiber optic wifi. (This home is a duplex.)

Popular amenities for house rentals in Lexington

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A large, heated swimming pool is visible at the center, surrounded by comfortable lounge chairs. Umbrellas provide shade for relaxation. A spacious outdoor area features a deck and is bordered by a lush green lawn, enhancing the inviting atmosphere for entertaining.

4.99 out of 5 average rating, 97 reviews

Close to Everything! Beautiful two-story home

5 out of 5 average rating, 64 reviews

A modern house is set against a scenic backdrop, featuring a landscaped yard with lush greenery. A swimming pool is positioned prominently, accompanied by lounge chairs for relaxation. A slide is also visible at the pool's edge, providing a recreational feature for guests.

Home in Nicholasville

Cliff House

Superhost

A two-story home is set in a serene outdoor space, featuring a spacious patio area by the pool. Lush greenery surrounds the space, and a flower pot with colorful blooms sits on a nearby table, enhancing the peaceful atmosphere.

4.68 out of 5 average rating, 65 reviews

Private for 4 No cleaning fee Discounts up to 20%

A spacious living area is centered around a decorative stone fireplace, complemented by a large flat-screen television mounted above. Comfortable leather seating and a wooden coffee table are arranged on a patterned area rug, with natural light entering through a nearby window.

4.87 out of 5 average rating, 47 reviews

My Old Kentucky Home

4.99 out of 5 average rating, 96 reviews

A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.

Home in Midway

The Bees Wing

A refreshing pool is surrounded by a wooden deck, featuring lounge chairs and a table with an umbrella. Floating toys are visible in the clear water, while lush greenery and trees provide a natural backdrop to the inviting outdoor space.

4.99 out of 5 average rating, 156 reviews

POOL/ game room! 8 beds 2 baths 3 bedrooms

4.87 out of 5 average rating, 39 reviews

A refreshing inground pool is set against a backdrop of rolling hills and greenery. Lounge chairs under umbrellas provide seating options. Decorative pink flowers in planters frame the pool area, while large inflatable floats add a playful touch to the water.

Home in Versailles

Sugar Hill Farm-Gorgeous Farmhouse w FirePit

4.95 out of 5 average rating, 121 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

Weekly house rentals

A comfortable family room is shown, featuring a cozy sofa set facing a white brick fireplace with a mounted TV above. Light-colored walls brighten the space, while an adjoining area reveals a dining area with a warm wooden floor and modern furnishings.

4.94 out of 5 average rating, 275 reviews

Close to downtown, can walk to UKgames!15.690.63-1

The Bourbon Room is presented with a king-size bed adorned with white linens and a mustard yellow throw. Two bedside tables with lamps flank the bed, while framed bourbon-themed artwork adds character to the light blue walls.

4.98 out of 5 average rating, 249 reviews

Bourbon Trail - 1Mi. To Downtown - Rupp - UK

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.

4.89 out of 5 average rating, 236 reviews

Perfect for Traveling Professionals & Vacation!

4.97 out of 5 average rating, 79 reviews

The exterior of the property showcases a spacious backyard with well-maintained grass, an outdoor fire pit surrounded by seating, and a hot tub visible beneath the deck. Soft lighting provides illumination as the sky transitions into dusk, highlighting the inviting atmosphere of the outdoor space.

Home in Versailles

Luxe Bourbon Trl~Game Rm~Golf Sim~Hot Tub~Fire Pit

A bourbon bar setup is featured, showcasing a wooden barrel labeled 'THE DISTILLERY' alongside a copper bourbon still. A drink is placed on the counter, surrounded by cocktail mixers, herbs, and sugar cubes. Natural light filters through a nearby window, highlighting the scene.

4.96 out of 5 average rating, 263 reviews

Distillery House Downtown w/ Hot Tub and Fire Pit

5 out of 5 average rating, 59 reviews

The Coffee House

A brick house is showcased with a well-manicured lawn, surrounded by green shrubbery and a small red-leafed tree. A driveway leads to a parked blue vehicle, while trees in the background add natural beauty to the setting.

4.98 out of 5 average rating, 171 reviews

Quiet neighborhood close to everything!

A cozy living area is designed with a combination of gray sofas and circular chairs surrounding a wooden coffee table. A gas log fireplace is framed by built-in shelves displaying decorative items, while natural light floods the space through large windows.

4.97 out of 5 average rating, 143 reviews

Golf Simulator | Hot Tub | Game Room | Firepit |

Private house rentals

An updated kitchen showcases stainless steel appliances and quartz countertops, complemented by blue cabinetry. A central island includes a gas cooktop. A dining area is featured, equipped with a table that seats six. Natural light floods the space through multiple windows.

4.93 out of 5 average rating, 68 reviews

Walk to Rupp Arena/3Bedroom/Parking

A bright corner nook is adorned with navy blue walls and floral wallpaper, creating a cozy ambiance. Two white tables with matching chairs are surrounded by comfortable seating featuring colorful cushions. Natural light enters through the large window, softly illuminating the space.

4.96 out of 5 average rating, 96 reviews

Cozy Pink House Near Downtown Lexington

4.9 out of 5 average rating, 29 reviews

Boutique 609 walk to restaurants and Rupp Arena

The living room features a comfortable sectional sofa, paired with a light-colored armchair. A dark coffee table sits in the center, accentuated by a decorative wooden piece. Natural light enters through the window, illuminating the soft hues of the furnishings and the wall art.

4.98 out of 5 average rating, 63 reviews

Roundtable Ranch

A modern kitchen features a large island with seating for four, adorned with stylish wooden stools. The sleek cabinetry is complemented by stainless steel appliances and pendant lighting. Natural light floods the space through large windows, providing a bright and airy ambiance.

5 out of 5 average rating, 33 reviews

Luxurious 3 BR Distillery District Townhouse

A cozy living area features a soft gray sofa paired with a minimalist floor lamp against a wall adorned with artwork. Natural light filters through horizontal blinds, casting gentle shadows across the space, while decorative plants add subtle greenery.

4.94 out of 5 average rating, 71 reviews

Berry Blessed/ Historic Bracktown

A spacious living room is presented, featuring a beige sofa, two brown armchairs, and a wooden coffee table on a patterned rug. A flat-screen TV is mounted on the wall, with a fireplace visible to the left. Natural light floods the room through large windows.

4.98 out of 5 average rating, 87 reviews

Hamburg Haus | King Suite|Garage |Horse Park 20min

An entryway and living area are shown, featuring a sleek black console table with decorative items, including a candle holder and vase. A cozy rug lies under a wooden coffee table, while a large television is mounted above a mantel. Artwork of a horse adorns the wall.