House rentals near Rupp Arena

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, 911 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, 172 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

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, 268 reviews

Distillery House Downtown w/ Hot Tub and Fire Pit

The Distillery House is a historic c. 1898 Kentucky farm house in the heart of downtown. Incredibly rebuilt in 2019 from the ground up with a modern touch. Amazing amenities like no other stay in town: Fully stocked bourbon bar mixers to make your own craft cocktails! (no alcohol) Real bourbon still to learn the bourbon making process! Private 6 person hot tub and fire pit! Bikes to ride the historic legacy trail! Plush bathrobes, entertainment center and more! 3 blocks to downtown!

Superhost

A cozy sitting area features exposed wooden beams and a decorative fireplace. Colorful armchairs are arranged around a central table, with a large flat-screen TV mounted on the wall. Natural light filters through the windows, enhancing the elegance of the space.

4.9 out of 5 average rating, 161 reviews

Historic and elegant Morrison Cabin built in 1787

The 1787 Morrison Log Cabin is located in the Gratz Park Historic District in Downtown Lexington & is the oldest house in Lexington on its original site. It’s a short walk to wedding venues,historic sites,the Convention Center,Opera House,Rupp Arena & the best dining and nightlife Lexington has to offer. Convenient to the Horse Park. The house is great for couples, business travelers & families.The completely renovated 1805 Thomas January Hemp House located next door is also available to rent.

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, 141 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!

A dining area features a sturdy wooden table surrounded by several dark chairs. Natural light enters through multiple windows adorned with blinds. A large rug with colorful stripes adds warmth to the space, while modern cabinetry and appliances complete the inviting kitchen design.

4.98 out of 5 average rating, 336 reviews

Wilton Manor, walk to Burl & Distillery-pets ok

Enjoy great restaurants, bars, and music venues in Lexington within walking distance. This 1940 bungalow is in an up-and-coming neighborhood has an inviting open floor plan design with a gorgeous kitchen, three bedrooms, and one bath. The house is close to the Distillery District, 5 minutes to downtown/Rupp Arena (1.3 miles), 10 minutes to UK, and 15 minutes to the Horse Park by car. STR Reg #15075605-2 - Maximum occupants 6-Guests are prohibited from allowing more than maximum occupancy

A bright living space features two sofas, one in teal and one in cream, accompanied by a wooden coffee table. Artwork adorns the walls above a decorative fireplace. A large television is positioned in the corner, while natural light streams through the windows, enhancing the welcoming atmosphere.

4.88 out of 5 average rating, 129 reviews

Historic West Second Downtown Home

Step into a piece of local history in this beautifully preserved urban home, where classic architecture meets modern comfort. This centrally located retreat offers easy access to the city’s best dining, culture, and nightlife, yet feels like a quiet escape the moment you walk through the door. High ceilings, original details, and thoughtfully curated furnishings create a warm, welcoming atmosphere perfect for relaxing after a day of exploring. Enjoy being right in the heart of it all.

4.95 out of 5 average rating, 242 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 comfortable living area features a gray sectional sofa adorned with green and white cushions. A round coffee table sits at its center, topped with a vase of flowers. Soft lighting is provided by a chandelier above, and a television is mounted on a textured wall.

4.99 out of 5 average rating, 174 reviews

Historic Mansion in Heart of Downtown Lexington!

Located in the heart of historic downtown Lexington, the home combines original craftsmen woodwork from 1902, yet modern amenities to provide an upscale stay. Fully remodeled in 2018, the home is walking distance to Rupp Arena, both the University of Kentucky and Transylvania University's campuses, fine dining at Jeff Ruby's, Tony's, Frank & Dino's and many others, as well as event spaces at the Limestone Hall, the Grand Reserve, and the newly completed Lexington Convention Center!

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.

4.93 out of 5 average rating, 143 reviews

3 bed (2kings) 2.5 bath spacious remodeled home

Great find in downtown Lexington 3 bed 2.5 bath, with two huge king beds, and a queen mattress. Multiple queen air mattresses as well. Located less than half a block from Lexington’s greyline station (restaurants and market) and new limestone bay golf simulator and surrounded by everything the city has to offer. • 600 feet to the greyline station (food and market) and 250 feet to the golf simulator • 1.2 mi to Main Street • 1.9 mi to UK Center • 15 mins (7 mi) to Keeneland

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, 465 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: