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

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!

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

Cozy, cute 2BR townhouse near downtown, businesses
Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

Top Shelf the only Airbnb in KY above a Distillery
The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

Arcadium Downtown KING BED Easy Parking 1st Floor
Located in a Victorian home this apartment is perfect for a trip into Lexington! Located just a block away from the Central Bank Center, the location is great. The beds are comfortable and the space is great for a night in or a quick walk downtown. We are located just minutes from Keeneland. UPDATE: Just added a 4player Arcade Emulator machine, with up to 5,000 games to keep you entertained. This custom arcade is a gamer’s dream, featuring thousands of console games and classic arcade games.

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 Downtown Apt - 1 block from Rupp
Walk to Rupp & all downtown has to offer from this cozy 1 bedroom apartment located on the first floor. The space 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 staying booking with us, welcome! We look forward to hosting you again soon. If you have stayed with us before, thanks for your loyalty.

My Old Kentucky Home-Downtown LEX's Premier Stay!
Welcome to My Old Kentucky Home downtowns premier Kentucky themed Air B&B. The best Airbnb in Lexington for a romantic or relaxing getaway! No detail or amenity was spared; private hot tub, plush bath robes, back deck, fire pit, patio and garden with views of the city. Full bourbon bar mixers provided to make your cocktails! ( no alcohol ) Central downtown-1 block from Rupp arena and 3 blocks from UK campus! For a video tour visit the last picture to see the link !

Cozy DT Loft in Victorian Home Great Location
Inside my historical home on a beautiful street in downtown Lexington. Located walking distance to many attractions. *Do not book if live in the Lexington Area without my approval. *Must be 21 years old to book *Free street parking *I allow 3 guests with added fee but do not recommend for more than 2 days. *My prices have gone up only because I have had bad luck with the guests that have booked with lower prices. I do now give discounts to my 5 star repeat guests!

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.

Uptown comfy Queen bed condo Central LEX
Enjoy a stylish experience at this centrally-located Airbnb. You will find your stay located in a nice quiet neighborhood right in the heart of town where you can get to many of the sights quickly both by foot, car and even a scooters that you’ll find around town and can be used via smart phone app. You will love your time spent visiting all Lexington and the surrounding areas have to offer from this prime area top floor condo!

*Gorgeous Hideout | Close to Everything*
Our Newly One Bedroom Apartment is conveniently located near University of Kentucky, Transylvania, National Avenue Warehouse District, The Legacy Trail, Restaurants, Fine Dining & Nightlife. Martine's Pastry conveniently located two doors down. 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.
Popular amenities for holiday rentals near Rupp Arena
Apartment rentals with wifi

Lexington's Artistic Bunker / 1BR Downtown Condo

*Bluegrass Getaway*

The FLAT at Bell Place - Downtown/Horse Park

💙The FLAT @ the LEX w/ Parking-Horse Park-Bourbon

The Retreat - Bluegrass Country Starts Here

Private Condo Downtown, Walk to Rupp Arena

Comfort meets luxury in this city condo!

HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator
Family-friendly house rentals

The Rosewood Cottage of Lexington I Elegant & Cozy

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

Distillery District Diamond-pet friendly

Maryland Luxury Downtown Manor

Quaint little farm house close to Keeneland/horses

Game room! 6 beds 2 baths

Midcentury Downtown in Warehouse Block District

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

"The Corner Pocket" -Fun in the Heart of Lexington

Canopy of trees

Swanky Boho - Downtown

The Guesthouse on Lime

10 minutes from Keeneland,airport, downtown and UK

Cozy Broadway Apartment

Downtown Dream Digs-Second Story

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

Walk to Rupp Arena/3Bedroom/Parking

3 bdTownhouse Downtown

Centrally Located Lex Apartment!

Cozy studio with private pool and firepit

Modern & Unique Shipping Container

Cozy Kenwick Bungalow in the Heart of Lexington

Victorian Apt Downtown Lexington

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




