Kid-friendly vacation rentals near Rupp Arena

4.93 out of 5 average rating, 771 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances, offering ample counter space. Natural light floods the room, highlighting the herringbone-patterned floor. A wooden dining table with white, upholstered chairs invites meals together, while decorative shelves accentuate the wall.

Home in Lexington

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!

4.81 out of 5 average rating, 118 reviews

A modern living area is showcased, featuring a sectional sofa and two armchairs. Large windows provide expansive views of Downtown Lexington, with urban buildings visible in the background. A dining table with chairs and a small coffee table add functionality to the space.

Condo in Lexington

175 LEX - Stunning Downtown Views on Main Street!

Offering unparalleled views of Downtown Lexington, immerse yourself into living like a local at 175 LEX. Condo 601 has recently been renovated featuring all the modern-day amenities a guest would desire when visiting Central KY. Residing on the 6th floor, this condo-hotel features one bedroom with a queen-sized bed, living room with sleeper sofa, full kitchen with quartz and washer/dryer in-unit. Walkable to Rupp Arena, local restaurants like Carson's, coffee shops, retail shops, & more!

A spacious living room is furnished with two light-colored armchairs and a leather sofa, providing comfortable seating. A wooden coffee table sits centrally on a decorative rug, and a vintage trunk is positioned nearby. A mounted television is visible on the wall, completing the aesthetic.

4.83 out of 5 average rating, 213 reviews

Historic Distillery View Apartment. KING BEDS!

Enjoy a stylish experience at this centrally-located apartment. Our historic Airbnb is located in Lexington’s first boarding house. Originally built in the 1800s as a place for travelers to stay as they passed through town. We are bringing the boarding house back to its initial intention. Thoughtfully decorated with comfort in mind you can sit back and relax while enjoying our cotton sheets, comfortable sofa, and unique touches that will make you feel like you live in a historic palace.

A spacious bedroom features a king bed with a light-colored coverlet against a backdrop of eclectic wall decor and built-in shelving. Textured rugs cover the hardwood floor, while large windows with patterned drapes allow natural light to fill the room, creating a cozy atmosphere.

4.98 out of 5 average rating, 570 reviews

Haven on High Street Private Apt Historic Home

Haven on High St. Quiet-gracious-comfy-one bedroom apartment in 1842 home. Off street parking. King bed in bedroom, comfy queen sofa bed in living room, claw foot tub. Eclectic decor-a visual artistic treat. By design, the space is not kid or pet friendly. Fully furnished kitchen+coffee, tea, snacks. Private apartment-shared courtyard. Walk to coffee shop, UK, Rupp, downtown dining. Beautifully landscaped gardens with patio and porch seating. Host lives next door and available-as needed.

An open living space features a compact kitchen with modern appliances, including a refrigerator and stove. A cozy sofa is positioned around a light area rug, and a small dining table is found nearby. Light enters through multiple windows, enhancing the homey feel.

4.95 out of 5 average rating, 197 reviews

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.

The bedroom features a spacious bed with multiple pillows and a cozy blanket. Light-colored walls enhance the bright ambiance, complemented by two windows on either side. A decorative wall hanging adds character, while bedside tables hold books and lamps for a welcoming touch.

4.81 out of 5 average rating, 265 reviews

The Loft @ West Second

Walk to Downtown! Located on West 2nd Street. Walkable to downtown and Rupp Arena and a block from trendy Jefferson street. This uniquely designed space will soothe and refresh after a long day of adventuring or bourbon tasting. Rupp Arena, The Civic Center, Triangle Park, The Burl and Distillery District and all that Downtown Lexington has to offer is at your fingertips. The University of Kentucky is less than 2 miles away, KY Horse Park and Keeneland are all within a 15 minute drive

A stylish living area features a spacious sofa adorned with decorative pillows, complemented by a glass coffee table. An ornate gold-framed mirror adds elegance to the wall, while a nearby lamp and art pieces create a cozy yet sophisticated ambiance.

4.98 out of 5 average rating, 118 reviews

The Guesthouse on Lime

A hidden treasure in the heart of the city. The space has a modern feel in a historic setting. Built in 1897, the building was first purposed as a tavern, and then housed several businesses through the years. In the 1980s, the building was renovated and transformed into two living spaces. This space is the first level, The Penthouse On Lime is the top level and is also available for rent. Original hardwood floors and high ceilings add to the charm of this gorgeous urban space.

A vintage living space features ornate floral wallpaper and rich, dark drapes. An elegant sofa and armchair provide seating, while a round dining table is adorned with a decorative bowl at its center. Golden light fixtures illuminate the area, enhancing the historic charm.

4.96 out of 5 average rating, 168 reviews

The Prohibition - Downtown Lex

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!

A bright studio is highlighted by vaulted ceilings and soft beige walls. A spacious bed is adorned with white linens, while a small dining area with two chairs and a table is positioned by a window. Natural light fills the room, enhancing the cozy décor.

4.88 out of 5 average rating, 110 reviews

Downtown Digs-Spacious Loft

This beautiful historic home in downtown Lexington is just a few minutes walk to several downtown attractions, Transylvania University, countless delicious local cafes and bars, a 20 minute walk to Rupp Arena and 25 minute walk to The University of Kentucky. The area is loaded with charm, the neighborhood is full of victorian architecture, and a park sits less than a block away. It is a 15 minute drive to the Kentucky Horse Park and 14 minute drive to Keeneland.

A spacious living area features a blue sofa, a decorative wall art of an elephant, and a small dining table with two chairs. Natural light illuminates the room through several recessed lights, highlighting the warm wood flooring.

4.9 out of 5 average rating, 221 reviews

Lovely Downtown Apt 1 Block from Rupp!

Walk to Rupp and all downtown has to offer from this cozy, one bedroom apartment. The space is 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 booking with us, welcome! We look forward to hosting you again soon. if you have stayed with us before, thanks for your loyalty.

A comfortable living area features a gray sofa positioned near a window. A round table sits in front of the sofa, accompanied by a decorative bowl. The walls display a multi-panel artwork depicting a tree branch with blossoms, complemented by a ceiling fan and natural light.

4.82 out of 5 average rating, 272 reviews

Heart of downtown.A block from court house.

This is a modern apartment in the heart of downtown. 1880 year old building, with a popular bar on the ground floor. It can be very noisy on Friday and Saturday nights from 10pm-2.30 am. We are ideally located for Rupp Arena, the Convention Centre, the Opera House, Kentucky Theatre and lots of great local restaurants. There is street metered parking outside $1 / hour Mon-Fri 8am to 5pm and free after 5pm and on weekends.