Vacation 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!

4.91 out of 5 average rating, 242 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.

4.96 out of 5 average rating, 318 reviews

A spacious sleeping area includes a bed with a light-colored duvet, framed by large windows. A cozy seating area features a plush chair and small table, while an artwork with vibrant colors adds character to the wall. Warm wooden flooring enhances the inviting atmosphere.

Loft in Lexington

Spring Street Loft by Rupp-Covered Parking + Deck

Brand new 2nd-level loft with free covered parking spot beneath, a huge deck and outdoor dining option. Directly across Maxwell St. from Rupp Arena's parking lot-you can't get any closer! This single unit building was built on stilts to maximize outdoor space and downtown views. Your perfect oasis in the middle of the action includes a full kitchen, laundry room, bathroom, living area and Smart TV. Come for a concert or stay awhile, you'll have everything you need during your trip to Lexington!

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, 365 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, 104 reviews

A spacious living area features a comfortable sofa adorned with patterned pillows. Natural light illuminates the wooden ceiling and warm tones of the furnishings. A decorative area rug complements a coffee table, while soft lighting from side tables enhances the inviting atmosphere.

Townhouse in Lexington

Modern Townhome Close to UK

Welcome to this modern townhome, located in the desirable Chinoe neighborhood. Steps away from Chinoe Shopping Center, you'll find a supermarket, salon, and several restaurants. It's just a quick drive to Kroger Field, and a short drive to the heart of downtown. So whether you're here to place a bet at the Keeneland racetrack, attend a concert at Rupp Arena, tour one of our many bourbon distilleries, or cheer on the Wildcats, you'll find that this townhome is in a convenient location.

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.

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, 120 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.