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!

Hot Tub/Movie Barn/Arcade/ Downtown/ Farm View

Get ready to be pampered in this newly renovated downtown bungalow with a farm view! Just a short walk to downtown shopping/eating and a short drive to several attractions. Amenities: ✔Luxury Shower Tower ✔Full/Completely stocked Kitchen(see below) ✔Hot Tub ✔Private Movie Barn/Theater ✔Firepit w/Private Backyard ✔Arcade ✔Towel Warmer Close To Everything ✔Near Several Stops On Bourbon Trail ✔7 Miles To Horse Park ✔14 Miles To Lexington ✔17 Miles To Keeneland ✔39 Miles To Ark Encounter

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.

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!

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.

The Clayton House | Chic & Cozy

Welcome to our stylish, newly renovated 2-bedroom, 1-bath home, centrally located just minutes away from Georgetown College! This spacious gem boasts an inviting open full-kitchen and living room concept, a back patio, and back yard. Whether you're visiting the college, exploring the town, or simply looking for a comfortable and modern retreat, The Clayton House is the ideal choice for your stay. Experience the perfect blend of convenience and comfort in this newly revitalized space. *No pets

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!

Urban Downtown Stay| Spacious Large Home | MLK

Welcome to "King's Quarters" - The whole group has room in this spacious, downtown stay located in the heart of Lexington's cityscape. This space is close to activities in the downtown area with a wide variety of restaurants and shops that are just a short drive away. It's just a walking distance from Transylvania University, a 5-minute drive from the University of Kentucky, and a 15-minute drive from Keeneland & the Bluegrass Airport. Enjoy your visit to the city at this lovely urban stay!

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

*Chevy Chase TH walk to UK|EV Charging*

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.

Springside Equine Getaway

Looking for an apartment that is a warm and inviting getaway? In addition to the elegant master bedroom, this apartment can also accommodate 2 additional guest for sleeping on the queen size pullout sofa for a total of 4 guest comfortably. Other additional comforts include a fully stock kitchen with a coffee bar and bathroom amenities. Take time to enjoy the quaint park across the street to experience some downtown Georgetown history to relax and unwind.

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.)