Vacation rentals with a fire pit near Rupp Arena

4.91 out of 5 average rating, 137 reviews

The spacious home is set against a clear blue sky, featuring a combination of dark wood siding and a brown roof. A large deck is visible at the rear, while the surrounding green lawn creates a serene outdoor setting.

Chalet in Wilmore

Timberframe on Farm Lexington, KY Solar Power

Our home and farm is very secluded and overlooks the KY River situated on the top of the Palisades. Minutes from Lexington, Keeneland, Shaker Village, Bluegrass Airport and the Bourbon Trail 5 bedrooms, vaulted ceilings, a 3000 SF home with screened porch and a hot tub. We have a good layout for wheelchairs and a portable wheelchair ramp if needed. Fire Pit, hot tub and hiking trails available. We use solar power for our energy needs! Our pond has no fish but we can direct u to a place to fish!

4.93 out of 5 average rating, 148 reviews

A serene view of a pond surrounded by lush greenery, showcasing an island of trees at the center. A walking path follows the water's edge, complemented by a swing bench positioned on the grassy shore, providing a peaceful spot to enjoy the scenery.

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.

Superhost

A spacious living area features a comfortable sofa, two accent chairs, and a coffee table. Natural light is provided by large windows, with greenery adding a touch of nature. Artwork is displayed on the walls, complementing the modern design of the open-concept space.

4.85 out of 5 average rating, 122 reviews

"The Carlisle" WARM MODERN STAY w/ Yard -Greyline

Quaint, freshly renovated home in a prime urban location. Close proximity to Downtown Lexington, 8 mins from the NEW Rupp Arena, and 15 minutes to Keeneland and the KY Horse Park. Not to mention, this property is located right next to Castlewood Park and the up-and-coming Greyline Station Marketplace- a perfect place to grab some local eats, treats, coffee, and donuts! The space is charming, cozy and great for groups- with 4 bedrooms, a large living room, and a fenced in yard with a fire-pit :)

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, 729 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...

4.95 out of 5 average rating, 174 reviews

A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.

Home in Versailles

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

4.91 out of 5 average rating, 246 reviews

A warm glow illuminates the exterior of the studio above the detached garage, highlighting the private saltwater pool. The pool features a clean, inviting surface, with a set of steps leading into the water. Nearby, sturdy lounge chairs provide relaxation options.

Guesthouse in Lexington

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

4.94 out of 5 average rating, 512 reviews

The charming exterior of the cottage is highlighted by two symmetrical windows and a central door framed with dark wood. Lush greenery properties a potted plant atop a rustic barrel and vibrant flowers adorn the window boxes, enhancing the inviting entrance.

Guesthouse in Lexington

The Bourbon House- Downtown Lex’s Premier Air B&B

Welcome to "The Bourbon House" Downtown Lexington's Premier spot to stay for an authentic Kentucky experience. This cottage was built by me from the ground up with no details spared to immerse my guests in the finest things Kentucky has to offer- Fully stocked bourbon bar mixers! (You supply bourbon) Hand crafted house and furnishing from reclaimed wood and bourbon barrels, private hot tub, bathrobes, garden, fire pit, and walking distance to downtown and Rupp arena

An aerial view showcases a spacious home surrounded by lush greenery. A rectangular pool is visible in the backyard, accompanied by several loungers and shaded seating areas. A patio with a large umbrella complements the serene outdoor space, inviting relaxation and gatherings.

4.96 out of 5 average rating, 108 reviews

LexFunZone! Pool! Hottub! GameRm! Cozy Backyard!

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, a sporting event, or just looking for a fun getaway, we have all the entertainment you need! Featuring a pool, hot tub, arcade machine, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary coffee bar and take in the cozy sounds by our fire pit in the back yard!

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, 101 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.

4.97 out of 5 average rating, 108 reviews

A charming outdoor area features a simple tent structure and a rustic wooden shed under the shade of lush green foliage. A natural stone path winds through the space, leading to the tent, while grassy patches and scattered rocks enhance the serene environment.

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.)

Superhost

The dining area features a wooden table set for four with white plates and silverware. A modern light fixture hangs above, providing illumination. A well-equipped kitchen is visible in the background, showcasing stainless steel appliances and light cabinetry, while a cozy living room can be glimpsed through the doorway.

4.85 out of 5 average rating, 177 reviews

Firepit | Outdoor Deck | Great Location

New remodel in Gardenside! This 4BR, 2.5BA is 2025 sq ft. Brand new kitchen with marble tops, island, stainless appliances, wall opened to family room w/fireplace, kitchen also provides dining area that opens to new deck with patio furniture and grill. Great central location, only 10 minutes from Keeneland, 20 minutes to the Kentucky Horse park and 9 min to UK. Each bedroom is equipped with memory foam mattresses.