Holiday rentals with outdoor seating near Rupp Arena

Mid-Century 3 BR In Heart of Downtown Lex

New contemporary home w/in walking distance to Rupp Arena, several 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.

The Fillys

This is our home and my Wife and I reside upstairs, The available space is our basement with a private entrance, large living room with YouTube TV, and comfortable seating for 7 people. Microwave & coffee machine with a mini fridge. Two bedrooms are available, each with a queen bed. A full bathroom and laundry. Back patio overlooking Cross Keys park with a pond and walking track. Downtown and Fayette mall are 10 minutes away, Keeneland race course and the airport are 5 minutes from the house.

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.

The Luxe/HotTub/Playground/12min KHP/30min Ark

Experience the perfect blend of old charm and contemporary. Nestled on a tranquil street, you'll find yourself just a short stroll away from boutique shops, delectable dining options, Georgetown College, and picturesque parks. Additionally, the Kentucky Horse Park and interstate access are conveniently minutes drive away. Outside, indulge in your very own private backyard retreat, complete with a soothing hot tub , stone grill for al fresco dining pleasure, and a playground for the kiddos.

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

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

Hot Tub | 7 Beds | Fire Pit | Patio & Grill

Totally remodeled, one and half story in the heart of Southland. The open floor plan includes new hardwood flooring, a totally equipped kitchen with new stainless steel appliances and granite countertops, all leading to a new deck off the eat in kitchen. The first floor offers two bedrooms with an updated bath and 2 linen closets. Upstairs you will find 2 very large bedrooms, with great closet space and tons of natural light, sharing a jack and jill bath with 48 inch vanities.

Bluegrass Retreat with Hot Tub! Near Horse Park!

Unbeatable location for the best experiences in Central Kentucky! You will be close to the Kentucky Horse Park, historic Keeneland, downtown Midway, the Ark Encounter, Rupp Arena and downtown Lexington, UK sporting events, golf courses, and several highly desirable distilleries including our personal favorite - Buffalo Trace Distillery. There are so many great restaurants nearby! Be sure to check out our Guidebook when you book a stay at Bluegrass Retreat.

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.