Vacation rentals with outdoor seating near Rupp Arena

West meets South in this Garden Cottage Retreat

STR PERMIT #15078463 A cozy backyard cottage nestled in historic Pensacola Park, part of the national register of historic places. Conveniently, located along Hwy 27 (Nicholasville Road). A stones throw from the University of Kentucky, Kroger Field, 3 hospitals (Baptist Health, UK, and Children's Hospital), and Lexington's celebrated state botanical garden: The Arboretum. This standalone cottage features one dedicated parking space, full amenities, garden views, and artistic embellishments.

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.

KY & Bourbon & Horses, Oh My! Close to Keeneland

This home has been completely renovated with flawless finishes and top of the line appliances. This is for the UPSTAIRS only. (No one else lives at the residence & is solely for Airbnb) 10 minutes from Keeneland & a few miles from hospitals. Convenient location to shopping and restaurants. Clean and comfortable living spaces. This is a chefs kitchen, that has double doors to a walk out patio. The bathroom has a Bluetooth fan. I’ve provided everything to make your trip enjoyable as possible.

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

The Statesman / Walk to Rupp / Superb Deck

The Statesman, in the heart of Lexington, allows opportunity to experience the conveniences of downtown by foot. This 3-story (stairs only) historic townhouse has undergone a face lift, having spared no expense with high end finishing. Enjoy modern day conveniences while maintaining the old-world charm. **Located above a local bar Henry Clay's Public House; noise is a potential on the second-floor bedroom/living room (3rd floor is less disturbed) from the live music; no parties allowed**

Location! Beautiful Downtown Apt, Across from Rupp

Beautiful, fully renovated (2021) apt in a historic building on Spring Street--as close as you can be to Rupp Arena and the Convention Center. PARKING IS AVAIL. You can walk to everything! Coffee shops, restaurants/bars & anywhere in downtown Lexington! Extra spacious & outfitted with comfortable furnishings, plush linens, basic kitchen amenities & new appliances. The home includes WIFI and two ROKU Smart TVs. Enjoy your morning coffee from the comfort of your large, private porch.

Bourbon Trail for couples. Downtown & Free Parking

#15066671-3 Cozy townhome in downtown Historic Mulberry Hill on Limestone. We can see Transylvania University campus... it's one block walk. An easy flat walk to Rupp Arena, restaurants & bars, craft breweries, downtown events, opera house, farmers market & more. Or a $7 Uber if the weather is bad. Just 8 miles drive to Keeneland Horse Racetrack and 9 miles to the Kentucky Horse Park. Check out our adjacent property with an identical floorplan. Our home is not suitable for kids.

Graffiti Art Haus - Walk to Central Bank Arena

Industrial art haus just 3 blocks to Rupp Arena, a short walk to the Distillery District & only one block from Jefferson Street, with lots of dining & drinking options (West 6th Brewing)! Our guests will enjoy covered parking, luxury bedding, 2 smart TVs, a well-stocked kitchen & commercial laundry with sleeping arrangements for 4 people (1 king bed & 1 sofa bed). Whether you're in town for a concert, Keeneland, a wedding, graduation or work - this art haus is the ideal getaway!

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 !

Swanky Boho - Downtown

Discover a trendy and stylish bohemian-inspired oasis. Immerse yourself in the vibrant and artistic ambiance, perfect for a memorable stay. Relax amidst eclectic decor, embrace the laid-back bohemian lifestyle, and indulge in the inviting atmosphere. With modern amenities and a prime downtown location near hip cafes, coffee shops, and nightlife, this is the ultimate choice for those seeking the boho-chic vibe. Unforgettable memories await in this captivating retreat.

Uptown Retreat- Fireplace, Sauna -Romantic Getaway

Welcome to Uptown Retreat, a cozy Lexington hideaway perfect for couples, solo travelers, and business guests. Relax by the fireplace or in your private sauna, cook in the efficient kitchenette, or enjoy the covered patio with Adirondack chairs. With fast Wi‑Fi, Smart TV, and a dedicated workspace, this stylish, comfortable retreat blends relaxation, convenience, and premium location in one guest-favorite space.

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