
Vacation rentals with outdoor seating near Rupp Arena
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Top-rated outdoor seating rentals near Rupp Arena
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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!

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.

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.

Graffiti Art Haus - Walk to Central Bank Arena
Industrial art haus just 3 blocks to Rupp Arena, a short walk to Gatton Park & only one block from Jefferson Street, with lots of dining & drinking options! Less than 1 mile to the Distillery District. 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!

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.

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

The Statesman / Walk to Rupp / Superb Deck
The Statesman, in the heart of Lexington, allows opportunity to experience the conveniences of downtown by foot. This 3-story (stairs only) historic townhouse has undergone a face lift, having spared no expense with high end finishing. Enjoy modern day conveniences while maintaining the old-world charm. **Located above a local bar Henry Clay's Public House; noise is a potential on the second-floor bedroom/living room (3rd floor is less disturbed) from the live music; no parties allowed**

Game of Thrones - Downtown
Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

Bourbon Trail for couples. Downtown & Free Parking
#15066671-3 Cozy townhome in downtown Historic Mulberry Hill on Limestone. We can see Transylvania University campus... it's one block walk. An easy flat walk to Rupp Arena, restaurants & bars, craft breweries, downtown events, opera house, farmers market & more. Or a $7 Uber if the weather is bad. Just 8 miles drive to Keeneland Horse Racetrack and 9 miles to the Kentucky Horse Park. Check out our adjacent property with an identical floorplan. Our home is not suitable for kids.

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

The Prohibition - Downtown Speakeasy with Hot Tub
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!

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
Popular amenities for outdoor seating rentals near Rupp Arena
House rentals with outdoor seating

The Rosewood Cottage of Lexington I Elegant & Cozy

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

Quaint little farm house close to Keeneland/horses

Horse Farm Creekside Cabin- 6 min to KY Horse Park

Liggett Lounge: Great location for ALL occasions

Keenland Special - 1 Mi to UK & Downtown & Rupp

IT WAS ALL A DREAM - Modern Luxury in downtown LEX

Beautiful 4-bedroom home, close to Downtown/UK
Apartment rentals with outdoor seating

Downtown 2BR | Walk to Rupp · Porch · Parking

Nonie's Abode

Riverview 2 … enjoy the view !

Private Farm Basement Apartment!

Morgan Street Apartment

The Blue House & Gardens: Unit 1

Luxury 2 bedroom condo close to downtown and UK

#3 Apt. in the Pink House
Condo rentals with outdoor seating

Rye'd Away Unit 505

Historic Downtown Condo

The Champion's Suite Unit 809

The Big Blue Wave - 2-Bedroom Condo by Rupp Arena

The Writer's Gambit Historic Suite Downtown

Teal & Barrel Unit 411

Mary LeGrand's Penthouse - Downtown
Other vacation rentals with outdoor seating

Walk to Rupp Arena/3Bedroom/Parking

Sleep-easy Lex steps to restaurants and Rupp Arena

3-Story Townhouse King En-Suites | Walk to Rupp

The Kentuckian/ Walk to Rupp

Cozy, cute 2BR townhouse near downtown, businesses

Luxury Stay at Kentucky Horse park-Newtown Springs

Creekside- Bourbon Trail Oasis

Fully sanitized, private Carriage House + King Bed
Destinations to explore
- Apartment rentals Rupp Arena
- Rentals with a washer and dryer Rupp Arena
- Rentals with a fireplace Rupp Arena
- Condo rentals Rupp Arena
- Rentals with a patio Rupp Arena
- Pet-friendly rentals Rupp Arena
- Rentals with a fire pit Rupp Arena
- House rentals Rupp Arena
- Rentals with outdoor seating Lexington
- Rentals with outdoor seating Fayette County
- Rentals with outdoor seating Kentucky
- Rentals with outdoor seating United States
- Ark Encounter
- Kentucky Horse Park
- Buffalo Trace Distillery
- University of Kentucky
- Castle & Key Distillery
- Four Roses Distillery Llc
- The Arboretum, State Botanical Garden of Kentucky
- Raven Run Nature Sanctuary
- Shaker Village of Pleasant Hill
- McConnell Springs Park
- Old Fort Harrod State Park
- Talon Winery & Vineyards
- Lovers Leap Vineyards and Winer
- Equus Run Vineyards
- Masterson Station Park
- Cove Spring Park
- Kroger Field
- Fort Boonesborough State Park





