House holiday 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, 147 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.

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.

4.89 out of 5 average rating, 245 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, 228 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.

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, 147 reviews

Central Lex Pool Oasis: HotTub! GameRm! Keeneland!

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, the University of Kentucky, or just looking for a fun getaway, we have all the entertainment you need! Featuring a POOL, HOT-TUB, ARCADE, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary FULLY STOCKED coffee bar and take in the cozy sounds by our fire pit in the back yard!

Superhost

Home in Versailles

4.83 out of 5 average rating, 141 reviews

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!!

5.0 out of 5 average rating, 105 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

The exterior of the home features natural stone accents, complemented by brown shutters on the windows. A well-maintained lawn with shrubs and seasonal foliage enhances the inviting entry. A concrete driveway provides parking, while a wooden deck is visible at the side of the house.

4.99 out of 5 average rating, 131 reviews

Creekside cabin in city. King bed. Walk in shower

Unwind in the perfect fusion of City convenience with Nature Vibes. The backyard is privately lined with Native shrubs, Creek and abundant hardwoods. Listen to the birds while enjoying your morning coffee on the spacious deck. Visit the prayer garden in the back of the property or swing next to the creek and fire pit. Shillito Park is within walking distance. The Bluegrass Airport, UK and Keeneland are approx 10 min. King bed and private bath in Master. TV in all rooms.

4.93 out of 5 average rating, 313 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. High quality touches on the inside and has a tranqiul 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.

4.9 out of 5 average rating, 124 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.

4.92 out of 5 average rating, 131 reviews

Room of Requirement Guest Suite STR #15063219-1

This space, my fully furnished, walk-out basement, is available again! Nestled in the middle of a centrally located neighborhood, I offer a comfortable space with private parking and access, while still only 10 minutes to University of Kentucky, 15 minutes to Bluegrass Airport & Keeneland and 25 minutes to the Kentucky Horse Park. Five restaurants, ice cream, coffee shop, grocery market, boutique shops are a 5 min walk away.

4.87 out of 5 average rating, 108 reviews

Prime Location! 2 Kings Patio Fenced Yard

Escape to our Guest Favorite boho-glam bungalow in Lexington's desirable Hartland area! This fully renovated 2-bed/1-bath home comfortably fits 4 with two king beds. Enjoy a stylish interior, a fully equipped kitchen, and a private, fenced backyard with a fire pit. Perfect for families, friends, and pets, you're just minutes from downtown, UK, and local distilleries. A chic and comfortable retreat awaits!

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.