Holiday rentals with a patio near Rupp Arena

An aerial view captures a two-story house with a dark roof and a white exterior, positioned next to a well-maintained lawn. A concrete driveway leads to the entrance, with paths of grass lining the edges. Surrounding buildings and greenery are also visible.

4.92 out of 5 average rating, 114 reviews

Victorian Apt Downtown Lexington

Cozy Downtown Retreat - Walk to Rupp Arena & Dining! Welcome to your ideal Lexington getaway! Nestled downtown, our cozy retreat is the city's best at your doorstep. A short walk from Rupp Arena, it's perfect for sports fans, concert-goers, and culture lovers. Enjoy a comfortable stay with a modern living area, fully-equipped kitchen, and plush bed. With top dining, shopping, and nightlife nearby, plus high-speed Wi-Fi and free parking, our home offers everything you need. Book your stay today!

Guest favourite

4.9 out of 5 average rating, 243 reviews

Cottage w/Jacuzzi - centrally located, comfy beds!

Keep it simple at this peaceful & centrally-located house with hot, clean jacuzzi year-round (jets are old!). Comfy beds, cozy linens & a good sleep are the hallmark of our BnB. The focus is family, friends & interacting through good ol’ conversation. Plenty of room in kitchen for good meals! Lots of books in the library for a good read & art from local artists - all for sale. Close to downtown, campus, NOLI District, New Circle, I-75/I-64. Great stay for traveling professionals, nurses/doctors.

A stylish bedroom features a spacious bed with light grey bedding and a decorative throw. Natural light fills the room from multiple windows, complemented by a ceiling fan and wooden beams above. A small seating area and a blue dresser add functional elegance.

4.92 out of 5 average rating, 297 reviews

Sunset Over Lex-Downtown w Deck at Rupp Arena

Spacious, light-filled apartment across from Rupp Arena, walkable to downtown and UK's campus. The bedroom features a king sized Sealy mattress and plush bedding. Enjoy a gorgeous bathroom, full kitchen, and huge second level deck overlooking Rupp. Located in a historic building but newly renovated, top to bottom. Equipped for remote work or relaxation with high speed internet and a Smart TV. Pioneer Split Units for AC and Heat. Free parking for easy access to conventions, concerts, and games.

Superhost

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.

4.87 out of 5 average rating, 366 reviews

1st Boarding House Lexington / Free Late Checkout

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.

4.96 out of 5 average rating, 136 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!

Superhost

A contemporary home features a striking combination of metal and wood exterior. Large windows allow natural light to fill the entryway. A small, landscaped area with shrubs frames the stone pathway leading to the entrance, creating an appealing facade.

4.9 out of 5 average rating, 170 reviews

Mid-Century 3 BR In Heart of Downtown Lex

New contemporary home w/in walking distance to Rupp Arena, breweries, coffee shops, restaurants & Transylvania University. Less than 2 miles to UK campus, 15 mins to Keeneland & the Ky Horse Park. We provide luxurious bedding, plentiful amenities, a chef's kitchen w/ stainless cookware, granite countertops & island. Stream your favorite channels using our hi-speed wifi on the 55" smart TV in the living room or the 43" smart TVs in each bedroom. (No cable.) Easy check-in w/ keyless entry.

4.98 out of 5 average rating, 134 reviews

A charming cottage exterior is framed by lush greenery and mature trees. The light gray siding is complemented by white columns at the entrance. A brick walkway leads to the front door, bordered by neatly manicured bushes and seasonal flowers.

Home in Georgetown

Quaint cottage on scenic horse farm

Welcome to the Cottages at Oxford Springs Farm. Enjoy a quiet stay in the largest cottage of our 3 newly remodeled rental properties, all located on this beautiful, small working thoroughbred farm. Views from every window capture the beauty of the bluegrass. Conveniently located only 10 miles from the Ky Horse Park, 5 mi from the quaint historic town of Georgetown, and 30 minutes from some of Kentucky’s greatest bourbon distilleries. For wildcat fans, Rupp Arena is only 15 minutes away.

4.97 out of 5 average rating, 244 reviews

A classic bungalow features a welcoming front porch, framed by two trees and a well-maintained lawn. The home is set back from the sidewalk, showcasing a path leading to the entrance. A spacious fenced yard is visible to the side, providing a private outdoor space.

Bungalow in Lexington

Cozy Kenwick Bungalow in the Heart of Lexington

Welcome to your home away from home in Kenwick, one of Lexington's favorite neighborhoods! This classic bungalow has 3 bedrooms (queen beds in 2 rooms and 2 twin beds in another room) plus a bright basement room with a sleeper sofa. Sit outside on the covered front porch or sit on the back deck and enjoy the fenced in yard. Kenwick is centrally located and is an easy drive to many popular destinations including downtown, UK, the bourbon trail, the Kentucky Horse Park, and Keeneland.

A spacious living room features a large, light-colored sofa adorned with decorative pillows, complemented by a stylish coffee table. A floor lamp and an armchair provide additional seating. Artwork depicting a horse decorates the wall, and a fireplace adds to the cozy ambiance.

4.84 out of 5 average rating, 121 reviews

*Chevy Chase TH walk to UK|EV Charging*

Cozy on Cochran is located in the heart of 40502! Enjoy our 2-bedroom, 1-bathroom apartment that has been recently renovated. This gem is located in the heart of the highly desired Chevy Chase where guests are able to walk to UK, the Arboretum, Kroger Field, & so much more. This unit is the left-side of a duplex equipped with all the modern-day amenities a guest could desire. Guests will live like a true Lexingtonian and will be conveniently located for all their stay needs.

4.94 out of 5 average rating, 235 reviews

Spacious King Suite | Horses, Fire Pit, Garage

The whole family will enjoy staying in a quiet & safe neighborhood that’s close to everything! There's lots of room for fun and you'll love the large, private patio and fenced-in backyard featuring a fire pit and hammock hung under the trees. You'll have easy access to favorite local restaurants, shopping, attractions, Kentucky Horse Park, Keeneland, Rupp Arena, downtown events, & the interstate (I-75 or I-64) within minutes. Registration No. 15078410 “dash” 1

A comfortable living room features a light gray sofa paired with two striped armchairs. A wooden coffee table sits in the center, and soft light filters through sheer curtains. A doorway leads to additional rooms, enhancing the space's openness.

4.9 out of 5 average rating, 241 reviews

Cozy 3 bedroom home perfect for families or work.

Nestled in the heart of Southland Drive, this 3 bedroom 2 bath ranch-style home offers comfort and convenience close to everything Lexington has to offer. Take a short walk to Southland Drive and experience some of the best places Lexington has to offer, or take a short trip to downtown, Keeneland, and all the major hospitals. Perfect for traveling professionals or families, come and relax and see all that the area has to offer.

The living area features exposed wooden beams and a spacious sectional sofa facing a large television. A round side table and a lamp provide soft lighting. A set of double doors leads to a bright seating area with large windows, enhancing the open feel.