Holiday rentals with a patio in Jessamine County

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.

Wilmore Cozy Corner Reg. #9575

For up to 2 adults and 2 kids. Escape to our charming, centrally located apartment in the heart of Wilmore, Kentucky. Nestled in a peaceful neighborhood, our space offers a tranquil retreat for visitors seeking comfort, convenience, and a touch of Southern hospitality. You'll immediately feel at home in our cozy and thoughtfully designed apartment greeted by the open-concept living area. The fully equipped kitchen, tranquil bedroom, and well-appointed bathroom will ensure a comfortable stay.

Serene barn loft in the heart of the Bluegrass

Relax and unwind in this charming barn loft nestled amidst 13 rolling acres on Honey & Vine Farm. This loft is the ideal honeymoon and anniversary space! Enjoy coffee in the morning from Adirondack chairs overlooking the pond, spectacular sunsets from the deck, and absolute serenity in this peaceful setting. Queen bed, private entrance, and beautiful sunsets. The goats and two horses love meeting new friends! 20 minutes to Danville and near hiking, lake Herrington, and Shaker Village.

New Construction/ Close to Herrington Lake

The White Chalet is a brand NEW construction home centrally located in a peaceful neighborhood in Lancaster, KY. Whether you are going to Keeneland, a sporting event, Herrington Lake, or just looking for a fun getaway, you will only be a short commute to all that Central KY has to offer! Featuring 4BR, 3BA, high end kitchen, hot tub, game room, and sauna, we have all the amenities needed for a short or long stay. We are 21mi to Downtown Lexington & 20mi to Wilderness Trail Distillery.

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.

The River Side Lodge- with private boat dock!

Welcome to The River Side Lodge at the Palisades! Relax and fish by the the river on your own private dock, roast marshmallows by the fire, play in our game room, grill out over looking the beautiful view, or just cuddle up on the couch Netflix and chill 😎 This property offers fun for the whole family, or a sweet get away for couples. While this area is a quiet little getaway surrounded by nature, it is only a 25 minute drive from Lexington and 15 minutes from Nicholasville!

Summer Bliss! Pool&FunZone Oasis! 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!

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.

The Gainesway Suite-Near UK/Hospitals/Keeneland

A posh Guest Suite in popular Gainesway! Centrally located in a friendly, established neighborhood. Minutes to Lexington's best Concert Venues, Restaurants, UK, Rupp, Hospitals, and Shopping! Private entrance, luxurious and stylish furnishings, plus your own laundry room! Perfect for a night in town, traveling for a ballgame or show, visiting our famous distilleries and Keeneland! The suite is also equipped for longer stays, business travelers, you name it!