
Places to stay near Rupp Arena
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Top-rated vacation rentals near Rupp Arena
Guests agree: these stays are highly rated for location, cleanliness, and more.

The Loft @ West Second
Book the 2nd floor Loft of this beautiful historic house. Located on West 2nd St. with easy on street parking. Walkable to downtown off ofJefferson 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.

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!

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!

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

175 LEX - Walkable Downtown Condo & Stunning View!
Offering unparalleled views of Downtown Lexington, immerse yourself into living like a local at 175 LEX! Condo 501 has recently been renovated featuring all the modern-day amenities a guest would desire when visiting Central KY. Residing on the 5th floor, this condo-hotel features one bedroom with a queen-sized bed, living room with sleeper sofa, full kitchen w/ quartz and private washer/dryer. Walkable to Rupp Arena, local restaurants like Carson's, coffee shops, retail shops, & more!

Canopy of trees
Enjoy this peaceful and centrally-located apartment. Across the street from the historic Henry Clay estate. Just a few miles from Rupp arena, Uk, stadium and downtown. A short drive to the horse park. Walking distance to restaurants. There is a $50 per pet fee. Please be sure to include pet in your booking. This is a one bedroom with a queen bed. The couch folds into a sleeper and there are curtains for privacy.. Street parking only. The back and driveway are our private areas

Hidden Gem|One Bedroom Apt Downtown Lexington
Our One Bedroom Apartment is conveniently located near Downtown Lexington; University of Kentucky, Transylvania, Thoroughbred Park, The Legacy Trail, Restaurants, Fine Dining & Nightlife. It is a Guest Favorite for many travel nurses! They call it their favorite tucked away spot. Martine’s Pastry conveniently located next door. Walk-able to nearby yoga studios, Historic Lyric Theater, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Approximately, 5 miles from I-75\I-64.

Downtown Digs-Spacious Loft
This beautiful historic home in downtown Lexington is just a few minutes walk to several downtown attractions, Transylvania University, countless delicious local cafes and bars, a 20 minute walk to Rupp Arena and 25 minute walk to The University of Kentucky. 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.

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.

Heart of downtown.A block from court house.
This is a modern apartment in the heart of downtown. 1880 year old building, with a popular bar on the ground floor. It can be very noisy on Friday and Saturday nights from 10pm-2.30 am. We are ideally located for Rupp Arena, the Convention Centre, the Opera House, Kentucky Theatre and lots of great local restaurants. There is street metered parking outside $1 / hour Mon-Fri 8am to 5pm and free after 5pm and on weekends.

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.)

💙The FLAT @ the LEX w/ Parking-Horse Park-Bourbon
Historic charm w/ modern comforts in this immaculate downtown first floor flat. Positioned at the entrance to Town Brach Distillery, this beautiful home is walkable to incredible restaurants and bars downtown Lexington - Don’t park in the front of the house, they will issue a ticket. * Rupp Arena 0.5 miles * Keeneland Racetrack 5.5 miles * Kentucky Horse Park 8 miles * STR Reg #15062369-2 - Maximum occupants 4
Popular amenities for vacation rentals near Rupp Arena
Condo rentals with wifi

Historic Downtown Condo

*Bluegrass Getaway*

Lexington's Artistic Bunker / 1BR Downtown Condo

Thoroughbred Retreat Unit 803

The FLAT at Bell Place - Downtown/Horse Park

2BR/2BA Condo in Downtown LEX!

Top Shelf the only Airbnb in KY above a Distillery

Comfort meets luxury in this city condo!
Family-friendly house rentals

Golf Simulator | Hot Tub | Game Room | Fire Pit

Horse Central-Be our Guest!

The Rosewood Cottage of Lexington I Elegant & Cozy

KY & Bourbon & Horses, Oh My! Close to Keeneland

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

Maryland Luxury Downtown Manor

Midcentury Downtown in Warehouse Block District

Cottage w/Jacuzzi - centrally located, comfy beds!
Apartment rentals with air conditioning

The Guesthouse on Lime

High style on the Bourbon Trail

10 minutes from Keeneland,airport, downtown and UK

Nonie's Abode

Cozy Broadway Apartment

The Blue House and Gardens: Unit 2

Comfy Retreat steps from UK/Chandler Hospital

Haven on High Street Private Apt Historic Home
Other great vacation rentals near Rupp Arena

Centrally Located Lex Apartment!

Downtown Townhome. Private Garage + Walk to Rupp.

Cozy Kenwick Bungalow in the Heart of Lexington

Victorian Apt Downtown Lexington

Mulberry Hill

Apt 1

Downtown/UK, Private, Quiet (Local ID 15067121)

Luxury 2 bedroom condo close to downtown and UK




