Vacation rentals with outdoor seating near Rupp Arena

4.97 out of 5 average rating, 122 reviews

A spacious living area features a blue sofa and matching armchairs, arranged around a coffee table. A large wall-mounted television is present, and a dining area with six chairs and a kitchen island is visible in the background. Natural light fills the room through large windows.

Townhouse in Lexington

Distillery Luxury - 3 bedroom Townhome (2)

Welcome to my spacious urban townhouse in the vibrant Distillery District! This prime location is close to the best entertainment, restaurants, and attractions that Lexington has to offer including Rupp Arena. Immerse yourself downtown where you can explore local breweries, distilleries, and music venues just steps away from your front door. Indulge in the culinary scene of the city with dining options to satisfy everyone. The home boasts 3 bedrooms with king sized beds and private bathrooms!

4.89 out of 5 average rating, 321 reviews

The spacious living room is highlighted by elegant wooden trim and large windows that allow natural light to fill the space. A plush dark leather sofa is paired with armchairs, while a decorative fireplace serves as a focal point. A side table complements the refined decor.

Apartment in Lexington

1st Boarding House in Lexington Most Histortic BNB

Welcome to Lexington’s oldest boarding house. Built in 1880 this massive landmark was constructed into rooms to accommodate train travelers. The property is found in the historic Woodward Heights, one block away from Rupp Arena and Lexington Center. Also, adjacent to the Lexington Brewing and Distilling Co. You can walk .5 miles the to downtown attractions or the distillery district. The home has been in our family for almost 40 years and, we are excited to welcome travelers, once again.

A spiral slide in vibrant burgundy extends from a wooden ceiling to the floor, creating a playful focal point in the space. Natural light filters through windows, illuminating the smooth wood flooring and surrounding area, which includes modern appliances and a stylish chair.

4.94 out of 5 average rating, 108 reviews

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!

A modern kitchen features stainless steel appliances, including a refrigerator and microwave. The granite countertop extends into a breakfast bar with four wooden stools. Pendant lights hang above, illuminating the space, while a window allows natural light to fill the area.

4.97 out of 5 average rating, 397 reviews

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

4.88 out of 5 average rating, 214 reviews

A spacious living room is highlighted by a large chandelier and a classic fireplace. Elegant furniture includes a gray sofa and two armchairs surrounding a coffee table. Natural light streams through tall windows, and the rich area rug adds warmth to the inviting space.

Townhouse in Lexington

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**

4.98 out of 5 average rating, 491 reviews

A custom California King wooden bed is featured within an immersive room, surrounded by dark hues and dramatic lighting. Adjacent is a unique chair and a traditional rug, enhancing the room's historical charm and fantasy theme.

Apartment in Lexington

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

4.96 out of 5 average rating, 204 reviews

A spacious bedroom features a comfortable bed with plush linens, complemented by a decorative area rug. Natural light enters through two windows, illuminating the room. An air conditioning unit is mounted on the wall, and a stylish lamp stands beside the bed.

Apartment in Lexington

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.

5 out of 5 average rating, 164 reviews

An ornate circular mirror with a gold frame is displayed on a white wall. The reflective surface captures a glimpse of the staircase visible through its reflection, showcasing a blend of modern and classic design elements in the space.

Loft in Lexington

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.

4.93 out of 5 average rating, 134 reviews

A modern living area features exposed ductwork and polished concrete floors, with a large mural adding a vibrant artistic touch. A comfortable sofa and ottoman, adorned with decorative pillows, face a sleek coffee table. The kitchen area is visible in the background with bar seating.

Loft in Lexington

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!

4.97 out of 5 average rating, 648 reviews

A private hot tub is surrounded by lush greenery and hanging ferns. The area features a charming, screened structure with large windows. Soft fabric curtains provide a sense of privacy, while brick pathways lead into a tranquil outdoor setting.

Guesthouse in Lexington

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 !

Superhost

The living area features a combination of two chairs, a love seat, and a dining table with four chairs. A television is positioned on a wooden unit across from the seating. Open shelves display decorative items, while a warm rug adds comfort to the space.

4.91 out of 5 average rating, 183 reviews

Entire Home Downtown Lex, 1 block from Rupp Arena

The best location! This FULL house offers a private fenced back yard with free street parking in the front and FREE private parking in the back. Located a short walk to -Town Branch Distillery (.2 mi walk) -Rupp Arena/Convention Center (.2 mi walk - You can literally throw a football into the Rupp Arena Parking lot) -Keeneland (10 min drive) -UK's campus (10 min walk, 5 min drive) City of Lexington Premises ID / Registration #: 150,826,85-1

Superhost

A charming house with a purple front door is shown, set on a spacious lot with a well-kept lawn. The driveway leads to a flat surface suitable for off-street parking. Trees and a wooden fence enclose the backyard, providing a sense of privacy.