Holiday rentals with a patio near Rupp Arena

Downtown Rupp Arena 2Bed/1Bath cozy home

KENCANTO-Kentucky Enchanted: 2 Queen beds and 1 bath. Convenient location, minutes from Rupp Arena and downtown Lexington. Jefferson Street, a block away, has several great restaurants, coffee shop, brewery, and our favorite gelato shop. Drinks, dinner and dessert in a 5 minute walk. From concerts at Rupp, shows at Lexington Opera house, to just dinner on the town and a restful nights sleep. This is your destination. Enchant your stay in Kentucky. Two Exterior security cameras onsite 24/7.

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

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!

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.

Good times on Woodbine! Close to UK/Downtown.

Fully renovated home in the southland neighborhood which provides 4 bedrooms (2 kings, 2 queens) and 2 ½ baths. Additionally, the first floor offers a spacious living and dining room, den and a new kitchen which includes all the essentials to make your visit a pleasant one. Centrally located and minutes to downtown, UK Campus, Kroger Field, hospitals, and the Distillery District. Plus, it is just 10 minutes from historic Keeneland and the airport. Premises ID/Local Registration #15082967-1

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!

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 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.

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.

El Retro- Mid Century Ranch near Horse Park & Rupp

Welcome to “El Retro.” Unwind in this comfortable Mid-Century Modern Home with a dedicated office space. When it’s time to relax, sit back on a comfy leather couch, watch your favorite shows or movies on a Smart TV, or cook delicious meals in our fully stocked kitchen. Don't worry about cleaning up after your stay! Our cleaners will take care of everything! Pet fee is an additional $150, due to extra cleaning! Premises ID/Local Registration #15085095-1

5BR/3.5BA house close to UK/Downtown/Chevy Chase

Newly renovated 2100 sq foot house, Located in the heart of Lexington, near Woodland Park and walkable to many destinations. 1 mile to downtown/Rupp Arena, 2 blocks to Chevy Chase, 15 min walk to UK campus or tailgating at Kroger Field. Under 20 min drive to KY Horse Park, airport and Keeneland. Grocery and restaurants within a few blocks. Onsite TANDEM parking in driveway for up to 5 cars or 4 trucks/SUVs. Multiple sets of 1/2 stairs throughout house.

Luxurious 1-bedroom with free parking on premise

Historical home located in the heart of Lexington, Kentucky. Few minute walk to Woodland Park, Kroger, Starbucks, bars, and restaurants. Gas station right around the corner. A convenient 3 minute drive and you're in the middle of downtown Lexington. Rupp Arena (1 mi), Kroger Field (1.5 mi), Keeneland (7 mi), Kentucky Horse Park (10 mi), Buffalo Trace Distillery (26 mi). 1GB fiber optic wifi. (This home is a duplex.)