Villa holiday rentals in Kentucky

Historic Estate Pool/Hot Tub, Louisville Retreat

Explore the renowned KY Bourbon Trail or the excitement of the Louisville KY Derby, only 45 minutes away. An ideal retreat for adventure & relaxation. Nestled on 2.1 picturesque acres near the Ohio River, this elegant historical home harmonizes classic charm & modern luxury. Prime location, adjacent to the River Walk boat launch, offers convenient access to water activities. Outdoor enthusiast will appreciate nearby hiking & biking trails at Buttermilk Falls & Otter Creek. Private Pool/Hot Tub.

Brand New Ultra Luxury Villa near Red River Gorge

Welcome to Skyvilla @ Red River Gorge! Brand New Ultra Luxury Cabin/Villa within 5 minutes from Red River Gorge and Natural Bridge State Park. Property consist of 3 BRs, 3 1/2 Baths. Each BR consist of an attached bath suite with fully tiled rain shower baths, double vanity sinks, quartz tops. Bedrooms include 2 King suites and 1 Queen Bed suite ( 2 queen beds). One King suite also includes a soaker tub. High volume ceilings throughout the foyer and living / dining area with open gourmet kit

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 Hot Tub River Road Picnic

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 trail, 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.

National historical home in the Heart of Lexington

Timeless Elegance in the Heart of Lexington Stunning 5bdrm, 3ba historical home located in downtown Lexington, Ky. Perfect for large groups, families, or friends looking for a memorable stay in this luxurious property combines charming historical details with modern amenities for the ultimate getaway. Just steps away from the iconic Rupp Arena. Whether you're attending an event, enjoying a day at Keeneland, or exploring distilleries, you’ll be in the ideal spot for it all. Listing ID15068130-1

Bourbon Villa at Daynabrook Farm with HOT TUB-2

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm-HOT TUB-1

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm with HOT TUB-4

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm with HOT TUB-6

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Villa On the Bourbon Trail with HOT TUB-3

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

Bourbon Villa at Daynabrook Farm with HOT TUB-5

Valentine’s Special – Every Weekend in February! Please see the images for more details. (The package deal is also available outside of weekends for an additional charge. The package is by request only and not applied automatically. Discounts do not apply to bookings made before February 1, 2026, but the package can still be added for an additional charge.) Our cozy cabins are nestled on a private farm — the perfect place to relax, reconnect, and make memories that will last a lifetime.

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.