Vacation rentals with a patio near Rupp Arena

A contemporary home features a striking combination of metal and wood exterior. Large windows allow natural light to fill the entryway. A small, landscaped area with shrubs frames the stone pathway leading to the entrance, creating an appealing facade.

4.89 out of 5 average rating, 157 reviews

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.

4.98 out of 5 average rating, 271 reviews

A spacious sleeping area includes a bed with a light-colored duvet, framed by large windows. A cozy seating area features a plush chair and small table, while an artwork with vibrant colors adds character to the wall. Warm wooden flooring enhances the inviting atmosphere.

Loft in Lexington

Spring Street Loft by Rupp-Covered Parking + Deck

Brand new 2nd-level loft with free covered parking spot beneath, a huge deck and outdoor dining option. Directly across Maxwell St. from Rupp Arena's parking lot-you can't get any closer! This single unit building was built on stilts to maximize outdoor space and downtown views. Your perfect oasis in the middle of the action includes a full kitchen, laundry room, bathroom, living area and Smart TV. Come for a concert or stay awhile, you'll have everything you need during your trip to Lexington!

4.91 out of 5 average rating, 187 reviews

Cottage w/Jacuzzi - centrally located, comfy beds!

Keep it simple at this peaceful and centrally-located house with hot, clean jacuzzi year-round (jets are old!). Comfy beds, cozy linens and a good sleep are the hallmark of our BnB. The focus is family, friends & interacting through good ol’ conversation. Plenty of room in kitchen for good meals! Lots of books in the library for a good read and art from local artists - all for sale. Close to downtown, campus, NOLI District and I-75 / I-64. Great stay for traveling professionals, nurses/doctors.

A charming brick home with a gabled roof is framed by lush green trees and landscaped garden beds. A stone pathway leads to the front porch, where two white chairs invite relaxation. The welcoming facade features multiple windows allowing natural light.

4.95 out of 5 average rating, 265 reviews

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.

4.89 out of 5 average rating, 334 reviews

The spacious living room is highlighted by elegant wooden trim and large windows that allow natural light to fill the space. A plush dark leather sofa is paired with armchairs, while a decorative fireplace serves as a focal point. A side table complements the refined decor.

Apartment in Lexington

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.

Guest favorite

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.

4.95 out of 5 average rating, 118 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!

Guest favorite

A spacious living room featuring a light-colored sectional sofa with ample seating, complemented by a dark wood coffee table. Large windows allow natural light to fill the space, framed by navy blue curtains. A ceiling fan enhances airflow in this modern area.

Condo in Lexington

4.91 out of 5 average rating, 106 reviews

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!

4.98 out of 5 average rating, 196 reviews

A classic bungalow features a welcoming front porch, framed by two trees and a well-maintained lawn. The home is set back from the sidewalk, showcasing a path leading to the entrance. A spacious fenced yard is visible to the side, providing a private outdoor space.

Bungalow in Lexington

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.

4.88 out of 5 average rating, 298 reviews

A private heated salt-water pool is surrounded by a spacious concrete deck, featuring two black lounge chairs for relaxation. Lush green trees provide a natural backdrop, enhancing the tranquil outdoor space. The pool's clear blue water invites enjoyment and leisure.

Guesthouse in Lexington

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

5 out of 5 average rating, 221 reviews

A private entrance is displayed, featuring a white door with glass panels above. Wood railing with modern iron designs surrounds a small porch area, creating an inviting entrance. The exterior wall is clad in gray siding, complemented by a stylish light fixture.

Guest suite in Lexington

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!

A cozy living area showcases a leather couch and a plush chair, inviting relaxation. A wooden coffee table sits in the center, while natural light filters through the windows with blinds. A minimalist artwork hangs on the green accent wall, enhancing the overall aesthetic.