House holiday rentals in Jessamine County

Large, 1980's 3BR w/full basemt in Upscale area

Spacious 1980's, two story, 3 bedroom, 2.5 bath in desirable Lexington, Ky neighborhood. Two Queen beds, One twin bed, two pull out Lazyboy sofas. Two Roku TV's. WIFI Perfect for large families desiring a quiet neighborhood while still within the heart of Lexington. Private driveway & on street parking is permitted. 20 minutes to Keeneland, 10 minutes to Rupp Arena, 8 minutes to the hospitals and UK campus. 5 minutes to Chevy Chase. Walking distance to Kroger and restaurants. ID15082024-1

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.

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.

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!

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.

Central Lex Summer Pool Oasis: Hot Tub! Game Room!

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!

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!!

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.

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.

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.

13mi to Keeneland/C&K Property/ Historic Farm

This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key. Featuring 4 bedrooms, 4.5 bathrooms, original Gothic style architecture, picturesque views of Kentucky’s rolling hills, curated antiques, original art & so much more! The Shanklin House is an extension of Castle & Key, where guests will enjoy considered finishes, bespoke Castle & Key welcome basket and a space designed to exceed all guest expectations.

Peaceful Tiny House Escape on a Working Farm

Escape to The Tiny House on the Farm, a cozy Modern Farmhouse retreat on a peaceful 12-acre working farm. Relax among sheep, chickens, and gardens, enjoy a queen bed, loft sleeping, full kitchen, outdoor grill, fire pit, and games. Just 20 minutes from Nicholasville, Danville, and Harrodsburg, it’s the perfect mix of country charm and convenient access. Book your stay for a serene, unforgettable getaway!