Vacation rentals with a fire pit near Rupp Arena

4.93 out of 5 average rating, 149 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.

4.95 out of 5 average rating, 247 reviews

A gravel driveway is framed by two stone entrance gates, leading into an expansive green property. Tall trees line either side, providing shade, while open fields stretch into the distance, suggesting a peaceful rural setting.

Farm stay in Georgetown

Horse Country Heaven

Come check out Dunn Driftin guest cabin in the heart of horse country and have your very own cozy hideout while experiencing all that central Kentucky has to offer. Take a tour of the top-notch thoroughbred farms, go on the Bourbon Trail adventure, explore the Ky horse park, catch a race at Keeneland (April & October), or venture out to Churchill downs or the Ark Encounter. Oh, and just so you know, we love dogs! Additionally, we provide horse boarding and even massage therapy for an extra fee.

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, 731 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, 256 reviews

Treehouse in Georgetown

★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!

4.95 out of 5 average rating, 176 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

4.97 out of 5 average rating, 144 reviews

A serene backyard space is presented, featuring a circular stone fire pit surrounded by four white Adirondack chairs. In the background, a covered area shelters a hot tub, and lush trees provide shade, creating a peaceful environment for outdoor gatherings.

Home in Georgetown

The Luxe/Hot Tub/12min to Horse Park/30 Min to Ark

Where elegant vintage meets modern design. Come and enjoy this historic home on a quiet street in downtown Georgetown. You will be within walking distance of shops, restaurants, Georgetown College, and parks. Home is also a ten minute commute to the Kentucky Horse Park and interstate. Equipped with a fully stocked kitchen, full dining room, and a Loft office space. You can enjoy your Private backyard oasis boasting a relaxing hot tub, fire pit, black stone grill, and outdoor tv.

4.91 out of 5 average rating, 250 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.

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.

4.97 out of 5 average rating, 109 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.)

5 out of 5 average rating, 161 reviews

Home in Frankfort

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, fully renovated, open space home in a country neighborhood setting. The home is the perfect retreat for your next getaway to Kentucky. Conveniently situated only a 1/4 mile from Castle and Key Distillery and 2 miles from Woodford Reserve. 1/2 mile from the highly rated restaurant and bourbon bar, The Stave. Indulge in the ultimate bourbon tasting experience, knowing that comfort awaits you at your cozy haven.

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.