Vacation rentals with outdoor seating near Rupp Arena

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.

4.89 out of 5 average rating, 129 reviews

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.

4.93 out of 5 average rating, 149 reviews

A spacious living room is presented, featuring a gray sofa and two matching armchairs. A wooden coffee table is centered on a soft area rug. Natural light filters through a large window, complemented by decorative wall art and a floor lamp.

Guest suite in Lexington

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.

4.99 out of 5 average rating, 119 reviews

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.

Guesthouse in Lexington

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.

A welcoming living area features a light gray sofa adorned with patterned cushions. A round pink coffee table is centrally placed, holding a tray of magazines. Natural light enters through large windows, illuminating the space, while a ceiling fan enhances airflow.

4.94 out of 5 average rating, 730 reviews

Adorable, Clean Lexington Cottage, Convenient to Everything

You'll love this bright, well-decorated home away from home! Located in an OPTIMAL location for all that Lexington and surrounding areas have to offer. Safe neighborhood. Xtra long driveway. Comfy beds. Fully fenced in backyard and large patio-NEW PHOTOS COMING SOON! *IF YOU HAVE MORE THAN 2 PETS, YOU MUST CONFIRM WITH ME BEFORE BOOKING. $40 P/PET FEE BEYOND 2. TOTAL # OF PETS ALLOWED DEPENDS ON TYPE/SIZE. YOU ARE RESPONSIBLE FOR ANY DAMAGE/STAINS TO BEDDING, FURNITURE, LANDSCAPING, ETC...

4.97 out of 5 average rating, 103 reviews

A spacious backyard is shown, featuring well-maintained green grass and tall trees providing shade. A hot tub and outdoor dining area are placed next to the house. A colorful playground is visible in the background, adding to the inviting atmosphere of the outdoor retreat.

Home in Georgetown

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.

4.98 out of 5 average rating, 473 reviews

A custom California King wooden bed is featured within an immersive room, surrounded by dark hues and dramatic lighting. Adjacent is a unique chair and a traditional rug, enhancing the room's historical charm and fantasy theme.

Apartment in Lexington

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

Superhost

The kitchen features a spacious layout with modern appliances, including a refrigerator and stove. White cabinetry contrasts with natural wood paneling. A large window allows natural light to fill the room, enhancing the granite countertops and laminate flooring.

4.92 out of 5 average rating, 123 reviews

Mid-Century Modern

Mid-Century modern home with an open floor plan in a quiet neighborhood. Located near Versailles Road and Cardinal Hill Hospital. Close to Bluegrass Airport and Keeneland. 10 minutes from downtown. Small pet friendly (<25lb) with a large fenced in backyard. Three bedrooms, two full baths. Extra Trundle bed and desk in one of the bedrooms. Washer and dryer. Fully equipped kitchen with Keurig coffee / tea. Wifi. Large rear patio. Large screened-in porch. Carport and plenty of parking.

A cozy living area features a comfortable grey sectional sofa, two modern chairs, and a round wooden coffee table. The space includes a wall-mounted TV above a fireplace, with natural light streaming through the windows, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 186 reviews

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.

A spacious living room features modern furnishings with a blue sofa and a brown armchair, creating a cozy atmosphere. Natural light illuminates the room, highlighting the decorative fireplace and mounted TV above it. A kitchen and dining area are visible in the background.

4.98 out of 5 average rating, 102 reviews

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.

4.91 out of 5 average rating, 221 reviews

An outdoor deck is furnished with a comfortable sectional sofa adorned with red and cream cushions. A glass-top table sits nearby. Colorful fabric canopies provide shade, while trees and buildings are visible in the background, contributing to a serene outdoor setting.

Apartment in Lexington

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.

4.97 out of 5 average rating, 109 reviews

A black horse grazes peacefully on green grass in the foreground, while a white horse is seen near a cozy mobile home in the background. The surrounding area is shaded by trees, providing a serene atmosphere.

Tiny home in Richmond

The Stepping Stone Ranch

Cozy little mobile home located on a very beautiful horse farm (we welcome you to book a trail ride while you stay, just write in advance so we can get it booked as we do sometimes fill up)! Terrific location, only 15 minutes from Lexington, with many other outdoor activities in the area as well (ziplining, kayaking, Fort Booneborough). Also very close to multiple awesome restaurants with fun atmospheres (Proud Mary, Boonedogs, Halls on the River, etc.)