Holiday rentals with a patio near Rupp Arena

Mid-Century 3 BR In Heart of Downtown Lex

New contemporary home w/in walking distance to Rupp Arena, several breweries, coffee shops, restaurants & Transylvania University. Less than 2 miles to UK campus, 15 mins to Keeneland & the Ky Horse Park. We provide luxurious bedding, plentiful amenities, a chef's kitchen w/ stainless cookware, granite countertops & island. Stream your favorite channels using our hi-speed wifi on the 55" smart TV in the living room or the 43" smart TVs in each bedroom. (No cable.) Easy check-in w/ keyless entry.

3BR-4 Beds-2BA close to UK/Chevy Chase/Downtown

Newly renovated 1930's home- walk to UK Campus, Chevy Chase, 1/2 mile to Kroger Field Tailgating. Approx 1 mile to downtown, 15 min to Keeneland and Airport. First floor boasts brand new kitchen, dining room, living room and one bedroom with attached full bath with standup shower. Upstairs with 2 bedrooms and full bath off hallway. All queen beds, 1 tempurpedic, one memory foam and 1 regular mattress. Basement with bonus bedroom/game area, queen bed. 2 washer/dryer sets in unfinished portion.

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.

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, kitchen 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!

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

Cozy Kenwick Bungalow in the Heart of Lexington

Welcome to your home away from home in Kenwick, one of Lexington's favorite neighborhoods! This classic bungalow has 3 bedrooms (queen beds in 2 rooms and 2 twin beds in another room) plus a bright basement room with a sleeper sofa. Sit outside on the covered front porch or sit on the back deck and enjoy the fenced in yard. Kenwick is centrally located and is an easy drive to many popular destinations including downtown, UK, the bourbon trail, the Kentucky Horse Park, and Keeneland.

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!

Sunset Over Lex-Downtown w Deck at Rupp Arena

Spacious, light-filled apartment across from Rupp Arena, walkable to downtown and UK's campus. The bedroom features a king sized Sealy mattress and plush bedding. Enjoy a gorgeous bathroom, full kitchen, and huge second level deck overlooking Rupp. Located in a historic building but newly renovated, top to bottom. Equipped for remote work or relaxation with high speed internet and a Smart TV. Free parking for easy access to conventions, concerts, and games.

Lexington KY | 2Mi to Downtown, Kroger Field & UK

💸 Save 15% – We Waive Airbnb Service Fees! ★ 2 mi to Rupp Arena • 2 mi to Kroger Field ★ 1 mi to University of Kentucky • 1 mi to Downtown Lexington Nestled near Woodland Park in the coveted Chevy Chase neighborhood, our home blends urban convenience with serene park views. Stroll to top restaurants, local breweries, and coffee shops—all just minutes away. Enjoy the best of Lexington—perfect for exploring, dining, and entertainment!