Holiday rentals with outdoor seating near Rupp Arena

1st Boarding House in Lexington Most Histortic BNB

Welcome to Lexington’s oldest boarding house. Built in 1880 this massive landmark was constructed into rooms to accommodate train travelers. The property is found in the historic Woodward Heights, one block away from Rupp Arena and Lexington Center. Also, adjacent to the Lexington Brewing and Distilling Co. You can walk .5 miles the to downtown attractions or the distillery district. The home has been in our family for almost 40 years and, we are excited to welcome travelers, once again.

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!

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

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

Location! Beautiful Downtown Apt, Across from Rupp

Beautiful, fully renovated (2021) apt in a historic building on Spring Street--as close as you can be to Rupp Arena and the Convention Center. PARKING IS AVAIL. You can walk to everything! Coffee shops, restaurants/bars & anywhere in downtown Lexington! Extra spacious & outfitted with comfortable furnishings, plush linens, basic kitchen amenities & new appliances. The home includes WIFI and two ROKU Smart TVs. Enjoy your morning coffee from the comfort of your large, private porch.

Bright Dwntn Loft | Lng/Shrt Stay | Fast WiFi | 5*

Indulge in downtown living. Warm welcome and skilled support from hosts. Skylit loft; 1906 house. Urban feel. Maybe urbane, too! Quiet+privacy, 42 steps above the street. Ample free parking. Excellent work situation; superfast fiber wifi. Perfect for long stays. Enjoy nearby restaurants, breweries, coffee, more! Luxurious queen bed and plush-y couch, poplar and pine floors, sleek kitchenette, tile/glass shower, Roku TV, keyless entry. 6 to Rupp, 20 to airport. Not safe for children.

Graffiti Art Haus - Walk to Central Bank Arena

Industrial art haus just 3 blocks to Rupp Arena, a short walk to the Distillery District & only one block from Jefferson Street, with lots of dining & drinking options (West 6th Brewing)! Our guests will enjoy covered parking, luxury bedding, 2 smart TVs, a well-stocked kitchen & commercial laundry with sleeping arrangements for 4 people (1 king bed & 1 sofa bed). Whether you're in town for a concert, Keeneland, a wedding, graduation or work - this art haus is the ideal getaway!

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!

The Gainesway Suite-Near UK/Hospitals/Keeneland

A posh Guest Suite in popular Gainesway! Centrally located in a friendly, established neighborhood. Minutes to Lexington's best Concert Venues, Restaurants, UK, Rupp, Hospitals, and Shopping! Private entrance, luxurious and stylish furnishings, plus your own laundry room! Perfect for a night in town, traveling for a ballgame or show, visiting our famous distilleries and Keeneland! The suite is also equipped for longer stays, business travelers, you name it!