Villa holiday rentals in Kentucky

Barr House Inn-historic 18 miles to LexKY/HorsePK

Be prepared to drive up to a beautiful antebellum home that was built approximately 1859 as an impressive Gothic Revival dwelling but after a fire in 1971, the front exterior was remodeled with huge pillars in the antebellum style. The Inn is approximately 18 miles from Lexington and 18 miles from the Kentucky Horse Park. Enjoy the experience of being in a quaint, small town with some of the most famous horse farms nearby. These include Claiborne, Runnymede, Stone and Adena Springs and more.

Bourbon Trail, Firepit

After a beautiful drive along a tree-lined-canopied road, you will find Mint Julep Villa, located on a private 1.3 acre lot and just one street over from the Ohio River. Mint Julep Villa, is tastefully decorated for you and your family to enjoy your stay in the Louisville and Prospect KY area. No matter if it's the Bourbon trails, the Kentucky Derby, the numerous concerts and the many other attractions to draw you to Kentucky, Mint Julep Villa will be a place you'd be attracted to as well.

Bourbon Villa at Daynabrook Farm with HOT TUB-2

Escape to the rolling bluegrass hills and experience the magic of Kentucky's Bourbon Trail, nestled on a private farm, perfect for making memories that will last a lifetime. Featuring A king and queen bed Full kitchen for effortless in-cabin dining Private hot tubs to soak in after a day exploring distilleries Scenic views of the countryside from your private back porch Convenient location to Lexington, Louisville, Frankfort, and Danville and a short 20 minute drive to Bluegrass Airport.

Bourbon Villa at Daynabrook Farm with HOT TUB-4

Escape to the rolling bluegrass hills and experience the magic of Kentucky's Bourbon Trail, nestled on a private farm, perfect for making memories that will last a lifetime. Featuring A king and queen bed Full kitchen for effortless in-cabin dining Private hot tubs to soak in after a day exploring distilleries Scenic views of the countryside from your private back porch Convenient location to Lexington, Louisville, Frankfort, and Danville and a short 20 minute drive to Bluegrass Airport.

Bourbon Villa at Daynabrook Farm with HOT TUB-6

Escape to the rolling bluegrass hills and experience the magic of Kentucky's Bourbon Trail, nestled on a private farm, perfect for making memories that will last a lifetime. Featuring A king and queen bed Full kitchen for effortless in-cabin dining Private hot tubs to soak in after a day exploring distilleries Scenic views of the countryside from your private back porch Convenient location to Lexington, Louisville, Frankfort, and Danville and a short 20 minute drive to Bluegrass Airport.

Villa On the Bourbon Trail with HOT TUB-3

Escape to the rolling bluegrass hills and experience the magic of Kentucky's Bourbon Trail, nestled on a private farm, perfect for making memories that will last a lifetime. Featuring A king and queen bed Full kitchen for effortless in-cabin dining Private hot tubs to soak in after a day exploring distilleries Scenic views of the countryside from your private back porch Convenient location to Lexington, Louisville, Frankfort, and Danville and a short 20 minute drive to Bluegrass Airport.

12acre Villa right by Keeneland-Keene Creek Estate

10,000sqft Villa on 12 acres of gorgeous Kentucky countryside! Located less than a mile from Keeneland with access to Back Gate Drive. The estate is surrounded by horse farms and has nearly 300yds of creek frontage, a forested preserve, and rolling green pastures. We allow 8 vehicles and up to 19 guests. Please note we are only allowed to host up to 4 unrelated individuals at a time, as per Fayette County rules. So, this property is great for large family get togethers!

Historic Briar Rose Estate | Sleeps 16 |

Briar Rose Estate: An Opulent Getaway in the Heart of Shelbyville, KY Welcome to Briar Rose Estate, where luxury, serenity, and timeless beauty converge. Nestled on 50 acres of Kentucky’s rolling green hills, our meticulously restored estate offers a peaceful escape from the ordinary. Whether you're seeking a relaxing retreat, a cozy family getaway, or a special place to celebrate life's moments, Briar Rose Estate provides the ideal backdrop for unforgettable memories.

Red River Gorge. Pool. Pets. Wi-fi

Nestled in the quiet town of Stanton, Kentucky; 10-15 minutes away from all that Red River Gorge has to offer. 45 min to Lexington. Our house is whimsical and spacious. Perfect for families! We have a huge kitchen to cook a meal and relax by the fire pit in our private courtyard that overlooks the mountains. Also our Private pool is available March-Nov. Pet friendly (3 pet max) with a fully fenced in back yard. Please add pets to the reservation and pay the pet fee.