Vacation rentals with a patio near Rupp Arena

Victorian Apt Downtown Lexington

Cozy Downtown Retreat - Walk to Rupp Arena & Dining! Welcome to your ideal Lexington getaway! Nestled downtown, our cozy retreat is the city's best at your doorstep. A short walk from Rupp Arena, it's perfect for sports fans, concert-goers, and culture lovers. Enjoy a comfortable stay with a modern living area, fully-equipped kitchen, and plush bed. With top dining, shopping, and nightlife nearby, plus high-speed Wi-Fi and free parking, our home offers everything you need. Book your stay today!

Cottage w/Jacuzzi - centrally located, comfy beds!

Keep it simple at this peaceful & centrally-located house with hot, clean jacuzzi year-round (jets are old!). Comfy beds, cozy linens & 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 & art from local artists - all for sale. Close to downtown, campus, NOLI District, New Circle, I-75/I-64. Great stay for traveling professionals, nurses/doctors.

Sunset Over Lex-Downtown w Deck at Rupp Arena

Spacious, light-filled apartment across from Rupp Arena, walkable to downtown and UK's campus. The bedroom features a king sized Sealy mattress and plush bedding. Enjoy a gorgeous bathroom, full kitchen, and huge second level deck overlooking Rupp. Located in a historic building but newly renovated, top to bottom. Equipped for remote work or relaxation with high speed internet and a Smart TV. Pioneer Split Units for AC and Heat. Free parking for easy access to conventions, concerts, and games.

Downtown 2BR | Walk to Rupp · Porch · Parking

Centrally Located 2-Bedroom in Downtown Lexington! Step into a charming 1910 second-floor apartment in the heart of downtown — walk to Rupp Arena, the Lexington Opera House, restaurants, and nightlife. Fully stocked kitchen with gas stove, air fryer, and all cookware. Keurig, coffee, and tea provided. Smart lock entry, private covered porch, washer/dryer with detergent, and thoughtful extras stocked throughout. Perfect for game days, Keeneland, or a Lexington getaway. Premise ID:11032400-1

1st Boarding House Lexington / Free Late Checkout

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.

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!

Creekside- Bourbon Trail Oasis

Welcome to Creekside, a unique vacation experience nestled in the heart of Versailles, KY. Steeped in nature, Creekside offers majestic views of the river with peaceful waterfalls. In the evening, gather round the crackling fire pit, creating memories under the stars. When you're ready to explore, you'll find downtown Versailles is just a 10-minute drive away. For bourbon lovers, we are just 25 minutes from the famous Woodford Reserve. We now have Starlink wifi to always keep you connected!

Great Location - 2 Mi. to Downtown - Rupp - UK

📍 Prime Location - Chevy Chase / Ashland Neighborhood 🚶 0.05 mi to restaurants, breweries & coffee shops 🌳 1 block to Woodland Park 🎓 1 mi to UK & Downtown 🏀 2 mi to Rupp Arena & Kroger Field ✈️ 5 mi to Blue Grass Airport Perfect for UK game days, concerts, bourbon tours, business travel, or a weekend getaway while enjoying one of Lexington's most walkable neighborhoods. 🏡 Renovated 1900s home with a Speakeasy & Flapper theme 📺 Smart TVs • 🛜 Fast Wi-Fi • 🚗 Plenty of parking

Modern Townhome Close to UK

Welcome to this modern townhome, located in the desirable Chinoe neighborhood. Steps away from Chinoe Shopping Center, you'll find a supermarket, salon, and several restaurants. It's just a quick drive to Kroger Field, and a short drive to the heart of downtown. So whether you're here to place a bet at the Keeneland racetrack, attend a concert at Rupp Arena, tour one of our many bourbon distilleries, or cheer on the Wildcats, you'll find that this townhome is in a convenient location.

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.

*One Mile to UK-In the heart of Chevy Chase*

Cozy on Cochran is located in the heart of 40502! Enjoy our 2-bedroom, 1-bathroom apartment that has been recently renovated. This gem is located in the heart of the highly desired Chevy Chase where guests are able to walk to UK, the Arboretum, Kroger Field, & so much more. This unit is the left-side of a duplex equipped with all the modern-day amenities a guest could desire. Guests will live like a true Lexingtonian and will be conveniently located for all their stay needs.

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!