House vacation rentals 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.

4.96 out of 5 average rating, 401 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 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, 922 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 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, 185 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, 128 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.

4.98 out of 5 average rating, 499 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, 736 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.

4.98 out of 5 average rating, 143 reviews

A charming cottage exterior is framed by lush greenery and mature trees. The light gray siding is complemented by white columns at the entrance. A brick walkway leads to the front door, bordered by neatly manicured bushes and seasonal flowers.

Home in Georgetown

Quaint cottage on scenic horse farm

Welcome to the Cottages at Oxford Springs Farm. Enjoy a quiet stay in the largest cottage of our 3 newly remodeled rental properties, all located on this beautiful, small working thoroughbred farm. Views from every window capture the beauty of the bluegrass. Conveniently located only 10 miles from the Ky Horse Park, 5 mi from the quaint historic town of Georgetown, and 30 minutes from some of Kentucky’s greatest bourbon distilleries. For wildcat fans, Rupp Arena is only 15 minutes away.

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, 149 reviews

Football SZN Pool Oasis:HotTub! GameRm! Keeneland!

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, 244 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

The exterior of a charming black house is seen with a wooden deck and string lights overhead. A fire pit with seating is positioned nearby on a gravel area, while a colorful playhouse stands in the yard, surrounded by expansive green grass.

4.95 out of 5 average rating, 160 reviews

Close to UK, great outdoor space 15.690.63-2

Absolutely adorable update ideally located within a mile from UK and Kroger Field, and a short walk to the vibrant Southland corridor. Open floor plan with three full bedrooms, including a master suite, and a full basement equipped for recreation or work. Fully fenced backyard retreat is the perfect place to gather for food and drinks by the fire. This cozy gem is the ideal place to experience all that Lexington has to offer. Per city ordinance we cannot allow more than 6 guests.

A cozy living area displays a comfortable sofa, complemented by a light gray wall. A coffee table sits centrally, with a television mounted on a light wood stand. Natural light filters through two large windows, dressed with blue curtains.

4.88 out of 5 average rating, 119 reviews

Cozy 1-bedroom in Lexington

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.)

A welcoming front porch features a solid door with an address number visible. A small, potted evergreen plant stands next to the door. A black chair with a red cushion is positioned nearby, alongside a geometric decorative table. The porch floor is finished in dark wood.

4.93 out of 5 average rating, 466 reviews

Big Rock Cottage

Charming Cottage located in Downtown Lexington. Completely remodeled - clean and pristine. Two bedrooms and two full baths. Fully equipped kitchen, Waher / Dryer and large back porch. Only 1/2 a block away from Legacy Trail and walking distance to Rupp arena and all downtown activities. Please note that this is located downtown you will see diversity both in culture and socio-economic status. :1506321-1:

Popular amenities for Lexington house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

A large, in-ground pool reflects the surroundings, framed by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a spacious deck attached to the house. The inviting outdoor space is ideal for relaxation and enjoyment.

4.84 out of 5 average rating, 141 reviews

4 BR 3 Bath 9 beds! Hot Tub, Pool, Movie room!

4.99 out of 5 average rating, 103 reviews

Close to Everything! Beautiful two-story home

4.98 out of 5 average rating, 169 reviews

POOL/ game room! 8 beds 2 baths 3 bedrooms

4.99 out of 5 average rating, 105 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

4.83 out of 5 average rating, 178 reviews

A hot tub is illuminated with blue LED lights, creating a serene atmosphere in a cozy corner. The tub features multiple seating positions and control buttons for easy adjustments. A wooden bench is placed nearby, offering a place to relax before or after use.

Home in Lawrenceburg

Restful Bourbon Trail Lodge with Pool and Hot Tub

4.96 out of 5 average rating, 25 reviews

Home in Paris

Bluegrass Bourbon Retreat/Pool/ Downtown Paris

4.89 out of 5 average rating, 45 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

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.

4.88 out of 5 average rating, 56 reviews

My Old Kentucky Home

Weekly house rentals

4.92 out of 5 average rating, 131 reviews

A charming exterior view of a single-story home is framed by a white picket fence, with a small seating area accessible by the entrance. Trees with autumn foliage create a colorful backdrop, and a clear blue sky enhances the welcoming appearance of the residence.

Home in Georgetown

The Clayton House | Chic & Cozy

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, 371 reviews

Relaxing Hot Tub | S’mores Fire Pit | Garage

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, 145 reviews

Maryland Luxury Downtown Manor

A cozy living area showcases a leather couch and a plush chair, inviting relaxation. A wooden coffee table sits in the center, while natural light filters through the windows with blinds. A minimalist artwork hangs on the green accent wall, enhancing the overall aesthetic.

4.88 out of 5 average rating, 200 reviews

El Retro- Mid Century Ranch near Horse Park & Rupp

4.97 out of 5 average rating, 339 reviews

A bedroom features a spacious bed with layered bedding and decorative pillows. Flanking the bed are two bedside tables with lamps. Sheer curtains allow soft light to filter in, creating a serene ambiance in the space.

Home in Chevy Chase

Chevy Chase Charmer

5.0 out of 5 average rating, 122 reviews

Home in Frankfort

Bourbon Central Waterfront Luxe near Buffalo Trace

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, 249 reviews

Perfect for Traveling Professionals & Vacation!

A modern kitchen is visible, featuring light gray cabinetry and a central island with seating. Stainless steel appliances and a sleek hood above the stove are included. A dining area with a round table and elegant chandelier is situated in the background, illuminated by natural light.

4.98 out of 5 average rating, 210 reviews

Winterberry Drive Entire house

Private house rentals

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.

4.93 out of 5 average rating, 147 reviews

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

4.97 out of 5 average rating, 131 reviews

The master bedroom features a spacious bed with a dark blue bedspread, complemented by light-colored pillows. Exposed wooden beams add a rustic touch to the ceiling. A large area rug sits beneath the bed, enhancing the room's warmth. A framed artwork is displayed on the wall.

Home in Georgetown

Springside Equine Getaway

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, 323 reviews

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

The cottage exterior is framed by lush greenery and a neatly maintained lawn, featuring a charming porch with rocking chairs. A stone pathway leads up to the entrance, surrounded by trees and open space, providing a serene rural setting.

4.94 out of 5 average rating, 178 reviews

Charming Cottage Home on a Horse Farm in the City!

4.93 out of 5 average rating, 220 reviews

Hot Tub | Walkable | Patio | Fire Pit | Game Room

A charming exterior of a single-story home is displayed, featuring dark blue siding and a welcoming front porch. Neatly trimmed shrubs frame the entrance, and an American flag hangs by the door. Sunlight bathes the scene, highlighting the surrounding greenery.

4.98 out of 5 average rating, 185 reviews

Cheerful and Cozy in the Heart of Chevy Chase!

4.99 out of 5 average rating, 111 reviews

The outdoor space features a DIY pickleball court, surrounded by well-maintained grass and bordered by planters. A gazebo and hot tub are visible adjacent to the brick house, while tall trees provide a serene backdrop to the inviting courtyard area.

Home in Midway

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

A modern living area features a comfortable brown sofa with decorative pillows and a round coffee table. Large windows with sheer curtains allow natural light to fill the space. A flat-screen TV is mounted above a white fireplace, and a stylish wicker chair adds additional seating.