Vacation rentals in Fayette County

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!

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Modern Loft | Parking Included, Walk to Downtown

• Walkable to Local Favorite Spots | Gratz Park, doodles • Located above a Speakeasy in Downtown Lexington (expect some sound from below! We provide a sound machine and earplugs for guests to use if needed 😁) • TVs in Living Room + Bedroom • Fully Equipped Kitchen • Free Off-street Parking Blackout blinds have been added to the living room windows! This removes the brightness from the security light mentioned in the reviews. Premise ID for Local Regulations & Licensing: 15018706 "dash" 1

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

Southern Hospitality! Best location close to UK!

This home has been completely renovated with truly flawless finishes. Approximately 1 mile from all hospitals; UK, Central Baptist, St.Joseph. New kitchen and appliances. Very convenient location to Keeneland, Shopping, and Restaurants. Extremely clean and comfortable living spaces. The living and bed rooms have been equiped with Tv’s. WiFi is included. The shower even has a Bluetooth fan for playing music in the shower. I’ve provided everything to make your trip as enjoyable as possible.

175 LEX - Stunning Downtown Views on Main Street!

Offering unparalleled views of Downtown Lexington, immerse yourself into living like a local at 175 LEX! Condo 508 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 washer/dryer in-unit. Walkable to Rupp Arena, local restaurants like Carson's, coffee shops, retail shops, & more!

The Rosewood Cottage of Lexington I Elegant & Cozy

Rosewood Cottage is one of Lexington's most unique and charming properties. Located steps away from Ashland Park and under 5 minutes to Downtown, this picturesque 1920's cottage offers history, charm and elegance in one extraordinary home. Relax with a bubble bath & champagne while reading a book from the host's curated collection, roast s'mores by the backyard firepit, or dive into some southern cooking in the newly renovated kitchen. This home away from home is not one to miss.

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.

National Historic O'neal Cabin

Originally built during the late 1700’s, this two-story log cabin was restored in 1995. The O'neal Cabin is listed on the National Register of Historic Places. Located in central Kentucky, six miles from historic downtown Lexington, the O’Neal Log Cabin is in the heart of horse country and the bourbon trail. Whether you are looking for a getaway, a place to stay during the horse sales or a retreat while you visit Lexington’s sites, the O'Neal Log Cabin is perfect retreat.

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

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