Holiday rentals with outdoor seating in Fayette County

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

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.

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.

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

Explore Bourbon Trail ♥Downtown & Free Parking

#15066671-2 Two spacious bedrooms, each with its very own full on-suite bathroom – think of it as a double dose of hotel-style comfort for the price of one! Not only is our place a cozy haven, but it's also nestled within a vibrant neighborhood...a leisurely stroll away from over a dozen restaurants, bars, craft breweries, a lively farmers market, & the opera house. If you peek out the window, you'll catch a glimpse of the charming Transylvania University campus, which is just a block away.

Distillery District Diamond-pet friendly

This 1948 bungalow in an up-and-coming neighborhood has two bedrooms/one bath. This house has all the updates you could ask of modern living including internet access, TVs with Roku, and keyless entry. Each bedroom has blackout curtains, ceiling fan and bedside power station. The bath is fully stocked with essential personal care items. The fenced-in back yard has a deck and a fire pit. STR Reg #15075605-1. Maximum occupants 4-Guests are prohibited from allowing more than maximum occupancy

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

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.

*Chevy Chase TH- (1) mile to UK/ EV Charger*

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 Prohibition - Downtown Speakeasy with Hot Tub

Welcome Flappers and Gents to 1928 the height of the Roaring 20's! The Prohibition is a historic Victorian home in the heart of Downtown Lexington, walkable to everything! Your stay will transport you to the greatest time and party in history! Victorian and Art-Deco Antiques and Décor Flapper and Gent Cloths for Photos Hidden Speak Easy Bed Room Bourbon Mixing Bar (No Alcohol) Private Hot tub Scavenger Hunt Bicycles Private Parking and Entrance So much more!

Relaxing Hot Tub | S’mores Fire Pit | Garage

Stay in one of Lexington's most desirable neighborhoods: quiet, safe, & in a low-traffic cul-de-sac that's also close to everything! Create lasting memories with friends & family: - Make s’mores by the fire pit under the stars! - Relax in the hot tub after a long day of travel! - Fenced in yard! - Coffee Bar! Just minutes from favorite local restaurants, shopping, attractions, downtown events, & the interstate (I-75 or I-64). Registration #15076499dash1