Holiday rentals with a washing machine and dryer near Rupp Arena

Restored charm! Walk to Rupp. Easy Keeneland drive

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 or sporting event at nearby Rupp Arena (5 minute walk), watch the horse races at Keeneland (10 minute drive down the road), tour the bourbon distillery right around the corner, or explore the unique offerings of downtown Lexington. Stay in the heart of it all!

The Flat @ West Second

Book the First floor of this beautiful historic house. Located on West 2nd St. with easy on street parking. Walkable to downtown just off Jefferson St with shops and restaurants. Hop skip or jump to the new Gatton Park. Easy walk to Rupp Arena, The Civic Center, Triangle Park and all that Downtown Lexington has to offer. Sweet access to The Bourbon Trail! The University of Kentucky is less than 2 miles away, KY Horse Park, The Bluegrass Airport, and Keeneland are all within a 15 minute drive.

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

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

Penthouse @ 175 LEX -Walk to Rupp Arena on Main St

Offering unparalleled 270-degree views of Downtown Lexington on Main Street with a private balcony! The Penthouse is newly constructed featuring a full kitchen with quartz countertops & breakfast bar, dining table, balcony, 3 bedrooms each with queen-sized beds, two bathrooms, full living room with two sleeper sofas and private washer/dryer. Located in the heart of Lexington, walkable to Rupp Arena, Keeneland and Carson's, there isn't a more convenient spot to stay close to the action!

Cozy Downtown Apt - 1 block from Rupp

Walk to Rupp & all downtown has to offer from this cozy 1 bedroom apartment located on the first floor. The space outfitted with a Smart TV, plush linens and towels, brand new washer/dryer, all new appliances, basic kitchen amenities and free off street parking on the premises for an effortless stay in Downtown Lexington. If this is your first time staying booking with us, welcome! We look forward to hosting you again soon. If you have stayed with us before, thanks for your loyalty.

Swanky Boho - Downtown

Discover a trendy and stylish bohemian-inspired oasis. Immerse yourself in the vibrant and artistic ambiance, perfect for a memorable stay. Relax amidst eclectic decor, embrace the laid-back bohemian lifestyle, and indulge in the inviting atmosphere. With modern amenities and a prime downtown location near hip cafes, coffee shops, and nightlife, this is the ultimate choice for those seeking the boho-chic vibe. Unforgettable memories await in this captivating retreat.

The Prohibition - Downtown Lex

Welcome Flappers and Gents to 1928 the height of the Roaring 20's! The Prohibition is a historic Victorian home in the heart of Downtown Lexington, walkable to everything! Your stay will transport you to the greatest time and party in history! Victorian and Art-Deco Antiques and Décor Flapper and Gent Cloths for Photos Hidden Speak Easy Bed Room Bourbon Mixing Bar (No Alcohol) Private Hot tub Scavenger Hunt Bicycles Private Parking and Entrance So much more!

Lovely Downtown Apt 1 Block from Rupp!

Walk to Rupp and all downtown has to offer from this cozy, one bedroom apartment. The space is outfitted with a Smart TV, plush linens and towels, brand new washer/dryer, all new appliances, basic kitchen amenities and free off street parking on the premises for an effortless stay in downtown Lexington. If this is your first time booking with us, welcome! We look forward to hosting you again soon. if you have stayed with us before, thanks for your loyalty.

Wildcat Den Downtown Rupp Arena *King*Sized*Bed*

Welcome to our Wildcat Den! Whether you are a UK fan or just traveling through Lexington this air bnb offers you comfort, tranquility, with a little bit of UK whimsy! The king bed is very comfortable made with 100% cotton sheets. And the blue sofa is made to melt into! And the location is walking distance or a quick (inexpensive) Uber ride to downtown restaurants and nightlife. Best of all it is ONE BLOCK OVER from the Central Bank Center/ Rupp Arena!

Downtown Dream Digs-Second Story

This beautiful historic home in downtown Lexington is just a few minutes walk to several downtown attractions, including Rupp Arena, Transylvania University, the University of Kentucky, and countless delicious local cafes and bars. The area is loaded with charm, the neighborhood is full of victorian architecture, and a park sits less than a block away. It is a 15 minute drive to the Kentucky Horse Park and 14 minute drive to Keeneland