Holiday rentals with outdoor seating near Rupp Arena

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Top-rated rentals with outdoor seating near Rupp Arena

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Top guest favourite
A charming stone cottage with a gabled roof is set back from a winding driveway, surrounded by landscaped gardens. The entrance is flanked by trees and shrubs, creating a serene and inviting environment. A foggy atmosphere adds a touch of mystery to the scene.
Guest house in Lexington
4.99 out of 5 average rating, 158 reviews

West meets South in this Garden Cottage Retreat

STR PERMIT #15078463 A cozy backyard cottage nestled in historic Pensacola Park, part of the national register of historic places. Conveniently, located along Hwy 27 (Nicholasville Road). A stones throw from the University of Kentucky, Kroger Field, 3 hospitals (Baptist Health, UK, and Children's Hospital), and Lexington's celebrated state botanical garden: The Arboretum. This standalone cottage features one dedicated parking space, full amenities, garden views, and artistic embellishments.

Guest favourite
The living room is showcased, featuring a comfortable full-size sofa and two armchairs. The walls are adorned with framed artwork, and a coffee table sits in the center. Soft lighting creates a welcoming atmosphere, complemented by colorful area rugs underfoot.
Townhouse in Lexington
4.88 out of 5 average rating, 513 reviews

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

Top guest favourite
An open living area features large glass doors that provide views of the greenery outside. Industrial elements, such as exposed beams and metal accents, complement a cozy seating arrangement with a sectional sofa and wooden coffee table. A dining table with bar stools is visible in the background.
Apartment in Lexington
4.95 out of 5 average rating, 244 reviews

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

Top guest favourite
A spacious living area features a comfortable sofa and a cozy chair, complemented by a geometric patterned rug. A coffee table sits in the center, with natural light illuminating the space. The open layout leads to a kitchen visible in the background, enhancing the inviting atmosphere.
Townhouse in Lexington
4.97 out of 5 average rating, 292 reviews

Explore Bourbon Trail ♥Downtown & Free Parking

#15066671-2 Two spacious bedrooms, each with its very own full on-suite bathroom – think of it as a double dose of hotel-style comfort for the price of one! Not only is our place a cozy haven, but it's also nestled within a vibrant neighborhood...a leisurely stroll away from over a dozen restaurants, bars, craft breweries, a lively farmers market, & the opera house. If you peek out the window, you'll catch a glimpse of the charming Transylvania University campus, which is just a block away.

Superhost
A modern kitchen features light-colored cabinetry and a granite countertop, equipped with stainless steel appliances. A window with soft yellow curtains allows natural light to brighten the space. Decorative tile backsplashes add a subtle touch, while a rug enhances the floor area.
Home in Lexington
4.91 out of 5 average rating, 636 reviews

KY & Bourbon & Horses, Oh My! Close to Keeneland

This home has been completely renovated with flawless finishes and top of the line appliances. This is for the UPSTAIRS only. (No one else lives at the residence & is solely for Airbnb) 10 minutes from Keeneland & a few miles from hospitals. Convenient location to shopping and restaurants. Clean and comfortable living spaces. This is a chefs kitchen, that has double doors to a walk out patio. The bathroom has a Bluetooth fan. I’ve provided everything to make your trip enjoyable as possible.

Top guest favourite
Home in Lexington
4.97 out of 5 average rating, 438 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

Top guest favourite
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
4.98 out of 5 average rating, 212 reviews

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.

Guest favourite
Apartment in Lexington
4.94 out of 5 average rating, 159 reviews

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!

Top guest favourite
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.
Guest house in Lexington
4.97 out of 5 average rating, 692 reviews

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 !

Top guest favourite
A vibrant seating area features a plush red sofa adorned with decorative pillows. A light marble side table sits nearby, complemented by an intricate metal screen and lush greenery. Warm lighting from hanging fixtures enhances the inviting atmosphere of the space.
Flat in Lexington
4.99 out of 5 average rating, 141 reviews

Swanky Boho - Downtown

Discover a trendy and stylish bohemian-inspired oasis. Immerse yourself in the vibrant and artistic ambiance, perfect for a memorable stay. Relax amidst eclectic decor, embrace the laid-back bohemian lifestyle, and indulge in the inviting atmosphere. With modern amenities and a prime downtown location near hip cafes, coffee shops, and nightlife, this is the ultimate choice for those seeking the boho-chic vibe. Unforgettable memories await in this captivating retreat.

Top guest favourite
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.
Flat in Lexington
4.92 out of 5 average rating, 263 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. Free parking for easy access to conventions, concerts, and games.

Top guest favourite
A warm wood-burning fireplace is framed by a brick wall, enhancing the cozy atmosphere. A serving tray holds two glasses, a bottle of wine, and decorative stones. Greenery is placed on the tray, adding a touch of nature to the inviting scene.
Flat in Lexington
4.98 out of 5 average rating, 213 reviews

Uptown Retreat- Fireplace, Sauna -Romantic Getaway

Welcome to Uptown Retreat, a cozy Lexington hideaway perfect for couples, solo travelers, and business guests. Relax by the fireplace or in your private sauna, cook in the efficient kitchenette, or enjoy the covered patio with Adirondack chairs. With fast Wi‑Fi, Smart TV, and a dedicated workspace, this stylish, comfortable retreat blends relaxation, convenience, and premium location in one guest-favorite space.

Popular amenities for rentals with outdoor seating near Rupp Arena