Holiday rentals with a patio in Lexington

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!

Newly renovated upscale house with high ceilings

Get away and cozy in at this clean and comfortable two bed, two bath private home centrally located in a convenient, quiet neighborhood less than a five-minute walk to Kroger, restaurants, coffee, and a yoga studio. Easily accessible to Fayette Mall and UK by car. Fully equipped kitchen for cooking meals, reclining sofa for relaxing, 65" TV, books and games. One new Sealy king bed and a bunk bed with one double and two twin mattresses (one trundle). Washer and dryer available for your use.

Cottage Circle Home

This charming home is nestled in a cozy neighborhood, offering a serene atmosphere and a strong sense of community. Conveniently located, it boasts easy access to a variety of restaurants, catering to different tastes and cuisines, just a short stroll away. Keeneland Racetrack, a track that runs in the fall and spring months, is only 8 minutes from the driveway! Additionally, a nearby grocery store ensures that daily essentials are within reach. Cottage Circle is waiting for YOU! ☺️

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.

Beautiful Bungalow w/High End Amenities💙🥃

Welcome to your Kentucky Home Experience this beautifully appointed bungalow positioned just one street over from the popular Jefferson to West Sixth Street. Walk or Uber to the following: Rupp Arena, 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 Reg #15071157-6 - Maximum occupants 6 - Guests are prohibited from allowing more than maximum occupancy *

Bright Cozy Stay| Fenced Yard| Near I-75 Horsepark

The Kearney: newly renovated home in the beautiful 'Kearney Hall' neighborhood, primely located off the 64/75 intersection. This home is a perfect 'trifecta' between Lexington, Louisville, & Cincinnati! Situated only 8 minutes from the KY Horse Park, 15 minutes from Downtown Lexington and Keeneland Racecourse. This quaint home blends cozy with natural, modern elements for a pleasant stay. Bring your crew to experience a day at the tracks, a bourbon tour, or a KY family getaway!

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.

Carriage House Gardenside

Privacy and Convenience are yours when you stay at the Carriage House Gardenside. Located in historic Winchester, Carriage House Gardenside offers easy access to Lexington, the Kentucky Horse Park, Keeneland Race Course, the Bourbon Trail and Red River Gorge. Situated across from College Park and steps away from Winchester's public gym (indoor swimming pool and fitness center). Space features a king sized bed, large TV, coffee bar, devoted work space and full bath.

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!

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.)

Modern & Unique Shipping Container

Stay in our unique space in the North Limestone area. The Shipping Container (8X20) features 1 bedroom (queen mattress) + 1 bath and kitchen. We are located 4 blocks from Greyline station. Drive downtown in under 10 minutes, or to Keeneland in just 15. Easy walk to Castlewood Park. Come & explore the artisan culture in our up-and-coming neighborhood.