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, 897 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, 159 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, 265 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, 139 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, 666 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, 488 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 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, 240 reviews

Perfect for Traveling Professionals & Vacation!

Traveling professionals, relocation guests, vacation guests, this is the perfect house for you! This 3 bedroom 2 bath ranch-style home w/ a garage has a gourmet kitchen and an open floor plan. Perfectly located in the heart of Lexington in a family-friendly neighborhood near Trader Joes, hospitals, restaurants, the Summit Shopping Center, Fayette Mall and a short trip to Keeneland or downtown Lexington. This is the perfect home away from home. All are welcome! Pet Friendly, per request!

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, 127 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, 300 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 *

4.95 out of 5 average rating, 239 reviews

Spacious King Suite | Horses, Fire Pit, Garage

The whole family will enjoy staying in a quiet & safe neighborhood that’s close to everything! There's lots of room for fun and you'll love the large, private patio and fenced-in backyard featuring a fire pit and hammock hung under the trees. You'll have easy access to favorite local restaurants, shopping, attractions, Kentucky Horse Park, Keeneland, Rupp Arena, downtown events, & the interstate (I-75 or I-64) within minutes. Registration No. 15078410 “dash” 1

A cozy living area features a blue sofa with striped cushions, complemented by a wooden coffee table. A television is positioned against the wall. Natural light brightens the space, and an open layout connects to the kitchen area in the background.

4.84 out of 5 average rating, 308 reviews

Jefferson's Downtown Cottage/Walk to W6th Brewery

Location, Location, Location. This charming historic 2Bedroom & 2Bath home has been completely remodeled. Built in 1890, this property features all the amenities a guest could ask for. Located within steps of West Sixth Brewery, two restaurants Smithtown Seafood & County Club and a Lextran Trolley pickup, guests are able to Live Like A Local. Experience Kentucky in the heart of Lexington while staying only 5 minutes from Rupp Arena!

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.