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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!

City Chic Loft - Downtown

Discover urban living at its finest in this impeccably clean and stylish boutique. Nestled in the vibrant heart of downtown Lexington, enjoy proximity to trendy cafes, bars, and restaurants. Relax on a plush California King bed and take advantage of the full kitchen and laundry. Whether for short or long stays, this sparkling-clean haven offers style and convenience. Immerse yourself in the city's vibrant energy while having a peaceful retreat. Don't miss out on this unforgettable urban escape!

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!

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.

LUXURY Downtown Retreat 💙 w/ King Tempur-Pedic Bed

Welcome to your Kentucky Home This beautifully remodeled historic property is located in Downtown Lexington. Walk to Rupp Arena, several cool bars/breweries and upscale restaurants. King Tempur-pedic mattress with sleeper sofa. 2 smart TV's and high speed internet service. Beautiful kitchen with gas range and stainless steel appliances. * Rupp Arena - 1 mile * Keeneland Racetrack - 7 miles * Kentucky Horse Park - 8 miles * STR Reg #15062369-5 - Maximum occupants 4

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!

LUX W 6th Penthouse w/ Private Balcony - King Bed

Welcome to your Kentucky Home Experience this beautifully appointed Penthouse Condo located on popular West Sixth Street. Walk or Uber to the following: Rupp Arena, Convention Center, Lexington Opera House, Transylvania University, many nearby bars, breweries, and your choice of upscale or laid-back restaurants. * Rupp Arena 2 miles * Keeneland Racetrack 9 miles * Kentucky Horse Park 11 miles STR #15071157 - Max Guests: 8

Premium Downtown Apartment, Entire Space

Located in the heart of downtown Lexington, the apartment has a full kitchen and living room, separate king-size bedroom with its own bath, walk-in shower and heated floors. Overlooking the Pavilion, it’s perfect for everything from Thursday Night Live to the local Farmer's Market. The best or urban living and everything you want is right outside the front door.