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, 907 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, 171 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!

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, 140 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 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.

4.91 out of 5 average rating, 672 reviews

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

This home has been completely renovated with flawless finishes and top of the line appliances. This is for the UPSTAIRS only. (No one else lives at the residence & is solely for Airbnb) 10 minutes from Keeneland & a few miles from hospitals. Convenient location to shopping and restaurants. Clean and comfortable living spaces. This is a chefs kitchen, that has double doors to a walk out patio. The bathroom has a Bluetooth fan. I’ve provided everything to make your trip enjoyable as possible.

4.98 out of 5 average rating, 492 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

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, 128 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.

4.91 out of 5 average rating, 304 reviews

NoLi Bungalow w/ King Bed - Horse Park, Keeneland

Welcome to your Kentucky Home Amazing beds, modern kitchen, fast WIFI in a beautifully designed space located in the vibrant, artistic NoLi district. This up and coming neighborhood is located North of Limestone (NoLi) w/ delicious restaurants, bars, bakeries and coffee shops nearby. * Rupp Arena 3 miles * Keeneland Racetrack 9.5 miles * Kentucky Horse Park 11 miles * STR Reg #15071157-5 - Maximum occupants 4 - Guests are prohibited from allowing more than maximum occupancy *

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, 142 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 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, 114 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, 464 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: