Vacation rentals with a fire pit near Rupp Arena

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the KY Horse Park and downtown Lexington. 30min to Keeneland. 45min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, fooseball and butlers pantry w/ coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

Retro Mid-Century English Cottage

Just minutes to Keeneland and Red Mile. You’ll be glad you found this hidden gem in the Horse Capital of the World. Close to everything but in a safe and friendly neighborhood. Within ten minutes (or less) to Keeneland, Downtown, Rupp Arena, The Distillery District, UK, Masterson Station Park, Legacy Trail, The Arboretum or a scenic drive down Old Frankfort Pike. Our cozy cottage boasts two bedrooms with queen beds, a huge back yard with privacy fence to relax in, wi-fi, and large screen tv.

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!

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

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

"The Carlisle" WARM MODERN STAY w/ Yard -Greyline

Quaint home in a prime urban location. Close proximity to Downtown Lexington, 8 mins from the NEW Rupp Arena, and 15 minutes to Keeneland and the KY Horse Park. Not to mention, this property is located right next to Castlewood Park and the up-and-coming Greyline Station Marketplace- a perfect place to grab some local eats, treats, coffee, and donuts! The space is charming, cozy and great for groups- with 4 bedrooms, a large living room, and a fenced in yard with a fire-pit :)

My Old Kentucky Home-Downtown LEX's Premier Stay!

Welcome to My Old Kentucky Home downtowns premier Kentucky themed Air B&B. The best Airbnb in Lexington for a romantic or relaxing getaway! No detail or amenity was spared; private hot tub, plush bath robes, back deck, fire pit, patio and garden with views of the city. Full bourbon bar mixers provided to make your cocktails! ( no alcohol ) Central downtown-1 block from Rupp arena and 3 blocks from UK campus! For a video tour visit the last picture to see the link !

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.

5BR/3.5BA house close to UK/Downtown/Chevy Chase

Newly renovated 2100 sq foot house, Located in the heart of Lexington, near Woodland Park and walkable to many destinations. 1 mile to downtown/Rupp Arena, 2 blocks to Chevy Chase, 15 min walk to UK campus or tailgating at Kroger Field. Under 20 min drive to KY Horse Park, airport and Keeneland. Grocery and restaurants within a few blocks. Onsite TANDEM parking in driveway for up to 5 cars or 4 trucks/SUVs. Multiple sets of 1/2 stairs throughout house.

Downtown Apartment in Victorian Home

You’ll love our place which is centrally located in the historic Woodward Heights neighborhood. We are close to Rupp Arena, Downtown Lexington, Keeneland, Town Branch Distillery, Red Mile, restaurants, and nightlife. Enjoy outdoor spaces, friendly hosts, and the clean and spacious apartment with high ceilings, rustic hardwood floors, and fresh, comfortable bedding. Local Registration Number 15082852

The Launch Pad: 4BR/3BA w/ EV Charger & Fast WiFi

Welcome to The Launch Pad, your premier base of operations in Lexington. Designed for leisure travelers or for traveling professionals, contractors, and corporate teams, this 4-bed/3-bath home is optimized for productivity and relaxation. Whether you are in town for a contract, a conference, or a long-term project, we provide the fuel and the tech you need to launch your day successfully.

Equestrian, Sports Fans, Bourbon Trailers

Convenient to airport, downtown, UK, great stayover point for Red River Gorge, Keeneland Racecourse. Great for business travelers. Onsite parking. No children under 12 years old. Enjoy the pool! Pool rules: 1) adult must accompany under 18 yr old when outside. 3) No addit'l guest without getting approval . 2) No glass allowed in pool area 3) Hours 11:00 a.m to 9:00 pm.