House vacation rentals in Jessamine County

The living room features vaulted ceilings and an open layout. A sectional sofa and a reclining chair offer comfortable seating, while a coffee table sits centrally. Light hardwood flooring and soft wall decor contribute to a bright and airy ambiance. A large TV is mounted on a nearby wall.

4.98 out of 5 average rating, 130 reviews

Newly renovated upscale house with high ceilings

Get away and cozy in at this clean and comfortable two bed, two bath private home centrally located in a convenient, quiet neighborhood less than a five-minute walk to Kroger, restaurants, coffee, and a yoga studio. Easily accessible to Fayette Mall and UK by car. Fully equipped kitchen for cooking meals, reclining sofa for relaxing, 65" TV, books and games. One new Sealy king bed and a bunk bed with one double and two twin mattresses (one trundle). Washer and dryer available for your use.

4.99 out of 5 average rating, 67 reviews

Two cows and a sheep are seen grazing on hay in a sunlit pasture. A white farmhouse can be observed in the background, surrounded by expansive green fields and a wooden fence, under a clear sky scattered with soft clouds.

Home in Wilmore

Milk & Honey Farm Cottage House

The Milk & Honey Farm Cottage House Farm Stay! Conveniently located in Wilmore, KY just 15 miles to Lexington! 5 minutes to Asbury University, 19 miles to Keenland and 13 miles to Shaker Village. Our peaceful Farm setting provides for a wonderful relaxing atmosphere, with all the amenities, and yet convenience to all that Central Kentucky has to offer! Come experience a working family farm, take a stroll and visit the animals, enjoy the sunset, and wind down in our comfortable cottage house.

A spacious living area features a comfortable grey sofa and armchairs arranged around a white coffee table. Light-colored curtains frame large windows, while a dining area with a dark wood table is visible in the background, alongside a modern kitchen with stainless steel appliances.

4.88 out of 5 average rating, 214 reviews

Perfect for Traveling Professionals & Vacation!

Traveling professionals, relocation guests, vacation guests, this is the perfect house for you! This 3 bedroom 2 bath ranch-style home w/ a garage has a gourmet kitchen and an open floor plan. Perfectly located in the heart of Lexington in a family-friendly neighborhood near Trader Joes, hospitals, restaurants, the Summit Shopping Center, Fayette Mall and a short trip to Keeneland or downtown Lexington. This is the perfect home away from home. All are welcome! Pet Friendly, per request!

The kitchen features smooth beige cabinetry and granite countertops, complemented by a stylish tile backsplash. Modern stainless steel appliances, including a refrigerator, oven, and microwave, are present. Ample storage is provided with numerous cabinets, creating a functional cooking space.

4.95 out of 5 average rating, 201 reviews

Southern Hospitality! Best location close to UK!

This home has been completely renovated with truly flawless finishes. Approximately 1 mile from all hospitals; UK, Central Baptist, St.Joseph. New kitchen and appliances. Very convenient location to Keeneland, Shopping, and Restaurants. Extremely clean and comfortable living spaces. The living and bed rooms have been equiped with Tv’s. WiFi is included. The shower even has a Bluetooth fan for playing music in the shower. I’ve provided everything to make your trip as enjoyable as possible.

5 out of 5 average rating, 43 reviews

A spacious guest house is set against a clear blue sky, featuring a wraparound porch with white railings. The exterior showcases a combination of light siding and wooden accents, with dormer windows adding charm. Lush green grass surrounds the property.

Home in Versailles

Home in Versailles on the Bourbon Trail

Guest house on beautiful 172-acre Country Estate in Versailles, KY (Woodford County). Large 4bd/3bth home located directly on Kentucky's famed Bourbon Trail and 15 minutes from the historic Keeneland Racetrack and Bluegrass (Lexington) airport. Bourbon fans will enjoy proximity to famous distilleries such as Woodford Reserve, Four Roses, Buffalo Trace, and more. Visit the locally famous Kentucky Castle and enjoy all the activities of the world renown Kentucky Horse Park and museum.

4.87 out of 5 average rating, 112 reviews

A cozy living area features two large sofas, complementing a rustic wooden coffee table. The space is illuminated by a floor lamp next to one sofa. Artwork, including butterfly prints and nature scenes, decorates the walls, while a patterned area rug adds texture.

Home in Versailles

Woodford Stables / Walk to Eckert's Orchard

Welcome to Woodford Stables, your serene retreat nestled amidst rolling hills and picturesque paddocks. This charming farmhouse boasts a modern kitchen, three inviting bedrooms, and two pristine bathrooms. Relax in the cozy living area, or step outside to savor breathtaking views. With horses grazing nearby, it's a tranquil escape. Conveniently located, you can stroll to Eckerts Orchard for a delightful local experience. Ask us about boarding your horses during your stay!!

5 out of 5 average rating, 89 reviews

A spacious bedroom is featured with a large, dark bed framed by two bedside lamps. A soft, blue throw blanket adorns the bed. A painting is displayed on the wall above, and a potted plant adds a touch of greenery in the corner.

Home in Wilmore

*KY Charm*Asbury-Lex-Keeneland-King bed-spacious

This spacious, private basement is the perfect lodging for visiting families, commuting students, or out-of-town explorers. Located in a peaceful subdivision in the quaint town of Wilmore, we're within walking distance to Asbury University and Seminary, Centennial Park, hiking trails, and a bustling main street with shops, cafes, and restaurants. We are an easy 20-30 minute drive from Lexington, Keeneland, Rupp Arena, and the Bluegrass Airport. Jess Co Permit #9248

A collage showcases various outdoor and indoor entertainment areas. A blue pool is surrounded by sun loungers. A hot tub is visible nearby. Inside, a game room features a pool table, air hockey, and arcade machine, highlighting multiple recreational options.

4.97 out of 5 average rating, 131 reviews

Lexington Holiday FUN-ZONE! Pool! Hottub! GameRm!

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!

4.93 out of 5 average rating, 294 reviews

A spacious bedroom features a comfortable bed dressed in soft bedding. Natural light is provided by a window, and a ceiling fan offers airflow. A wooden dresser and two nightstands add functionality, while tasteful decor pieces enhance the inviting ambiance.

Home in Nicholasville

Cali King beds w/ Koi pond Oasis. 15 min from LEX

Nicholasville's finest short term rental! We recently finished remodeling this spacious ranch home in Nicholasville Ky and are extremely excited to share it with future guests. It looks brand new on the inside and has an awesome oasis in the backyard with water effects/ koi pond. It is close to all the great things to do in Lexington including Keeneland and the University of Kentucky. Mattresses are top of the line and will ensure you have a very comfortable stay.

A bedroom features a large tufted headboard against light blue walls. The bedding consists of a blue coverlet with a Kentucky theme. A desk area with built-in shelves displays decorative items, while a framed picture is mounted above the desk.

4.91 out of 5 average rating, 110 reviews

Top Lexington, Ky Stays- No Cleaning Fee

Spacious 3 bedroom, 1.5 bath home in one of the safest neighborhoods in Lexington, Ky. Perfect for families wanting a quiet escape from the hustle & bustle while still in the heart of Lexington. Conveniently located to Keeneland, Fayette Mall, Blue Grass Airport, Shillito Park,Rupp Arena, Jeff Ruby's, Distilleries, 5.5 miles to The Infield at Red Mile (Railbird Festival) Walking distance to The Summit at Fritz Farm. Within a 45 min drive to Red River Gorge.

A cozy living room features a light-colored sofa and armchairs arranged around a circular coffee table. A large area rug lays beneath, providing warm tones. Natural light enters through the window, while a mounted TV is positioned above a non-operational fireplace.

4.96 out of 5 average rating, 85 reviews

Minutes to Keeneland/Airport/UK & more!

Welcome to The Lex! This adorable house is the perfect place for your stay in Lexington, KY. Located in a quiet residential neighborhood - Kroger, Speedway, Starbucks, & several dining options are just a 2-minute drive away. We pride ourselves on providing guests with a clean, comfortable, & welcoming home. We hope you enjoy your stay with us and create wonderful memories that will last a lifetime. Book your stay now and experience the best of our city!

An open living space is showcased, featuring a brown sectional sofa and a round coffee table with a small plant. A ceiling fan is mounted overhead, while a dining area with a wooden table and chairs is visible in the background, complemented by a modern art piece on the wall.