Holiday rentals in Lexington

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Restored charm! Walk to Rupp. Easy Keeneland drive

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This renovated Victorian home in downtown Lexington is within walking distance of excellent dining, distilleries, and entertainment. Attend a concert or sporting event at nearby Rupp Arena (5 minute walk), watch the horse races at Keeneland (10 minute drive down the road), tour the bourbon distillery right around the corner, or explore the unique offerings of downtown Lexington. Stay in the heart of it all!

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.

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

Cozy Downtown Apt - 1 block from Rupp

Walk to Rupp & all downtown has to offer from this cozy 1 bedroom apartment located on the first floor. The space outfitted with a Smart TV, plush linens and towels, brand new washer/dryer, all new appliances, basic kitchen amenities and free off street parking on the premises for an effortless stay in Downtown Lexington. If this is your first time staying booking with us, welcome! We look forward to hosting you again soon. If you have stayed with us before, thanks for your loyalty.

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

Bright Dwntn Loft | Lng/Shrt Stay | Fast WiFi | 5*

Indulge in downtown living. Warm welcome and skilled support from hosts. Skylit loft; 1906 house. Urban feel. Maybe urbane, too! Quiet+privacy, 42 steps above the street. Ample free parking. Excellent work situation; superfast fiber wifi. Perfect for long stays. Enjoy nearby restaurants, breweries, coffee, more! Luxurious queen bed and plush-y couch, poplar and pine floors, sleek kitchenette, tile/glass shower, Roku TV, keyless entry. 6 to Rupp, 20 to airport. Not safe for children.

Hidden Gem|One Bedroom Apt Downtown Lexington

Our One Bedroom Apartment is conveniently located near Downtown Lexington; University of Kentucky, Transylvania, Thoroughbred Park, The Legacy Trail, Restaurants, Fine Dining & Nightlife. It is a Guest Favorite for many travel nurses! They call it their favorite tucked away spot. Martine’s Pastry conveniently located next door. Walk-able to nearby yoga studios, Historic Lyric Theater, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Approximately, 5 miles from I-75\I-64.

The FLAT at Bell Place - Downtown/Horse Park

Welcome to the historic Bell Court community, a close-knit neighborhood w/ lots of children & discerning families. Parties & other activities that do not meet the standards of the community will not be tolerated. Beautifully appointed 1st floor flat w/ stylish decor, a super comfortable bed & fast WIFI. * Rupp - 2 miles * Keeneland - 9 miles * Horse Park - 11 miles * STR Reg #15071157-1 - Max occupants 4 - Guests are prohibited from allowing more than Max occupancy *