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!

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.

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 charming, dark-colored cottage is set amidst lush greenery. A covered porch is visible at the front, featuring comfortable seating. Flower beds and manicured landscaping enhance the natural surroundings, while tall trees provide shade and tranquility.

Cabin in Versailles

4.88 out of 5 average rating, 98 reviews

Creekside- Bourbon Trail Oasis

Welcome to Creekside, a unique vacation experience nestled in the heart of Versailles, KY. Steeped in nature, Creekside offers majestic views of the river with peaceful waterfalls. In the evening, gather round the crackling fire pit, creating memories under the stars. When you're ready to explore, you'll find downtown Versailles is just a 10-minute drive away. For bourbon lovers, we are just 25 minutes from the famous Woodford Reserve. We now have Starlink wifi to always keep you connected!

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.

4.97 out of 5 average rating, 242 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.

4.92 out of 5 average rating, 303 reviews

Two outdoor bathtubs are positioned on a wooden deck, surrounded by trees and views of the creek. An Adirondack chair sits nearby, providing a space for relaxation while enjoying the natural surroundings.

Treehouse in Georgetown

KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs

Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. The highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station ✔ Hot Water

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.

A spacious outdoor area features a hot tub accompanied by two cozy lanterns on a patio beside a lush green lawn. Four adirondack chairs are arranged for relaxation, framed by the home's light-colored exterior and contrasting dark shutters.

4.95 out of 5 average rating, 350 reviews

Relaxing Hot Tub | S’mores Fire Pit | Garage

Stay in one of Lexington's most desirable neighborhoods: quiet, safe, & in a low-traffic cul-de-sac that's also close to everything! Create lasting memories with friends & family: - Make s’mores by the fire pit under the stars! - Relax in the hot tub after a long day of travel! - Fenced in yard! - Coffee Bar! Just minutes from favorite local restaurants, shopping, attractions, downtown events, & the interstate (I-75 or I-64). Registration #15076499dash1

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.

4.98 out of 5 average rating, 192 reviews

LUX W 6th Penthouse w/ Private Balcony - King Bed

Welcome to your Kentucky Home Experience this beautifully appointed Penthouse Condo located on popular West Sixth Street. Walk or Uber to the following: Rupp Arena, Convention Center, Lexington Opera House, Transylvania University, many nearby bars, breweries, and your choice of upscale or laid-back restaurants. * Rupp Arena 2 miles * Keeneland Racetrack 9 miles * Kentucky Horse Park 11 miles STR #15071157 - Max Guests: 8

A cozy living area displays a comfortable sofa, complemented by a light gray wall. A coffee table sits centrally, with a television mounted on a light wood stand. Natural light filters through two large windows, dressed with blue curtains.