Villa holiday rentals in Kentucky

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Top-rated villa rentals in Kentucky

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Top guest favourite

Villa in Brandenburg

5 out of 5 average rating, 15 reviews

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.

Guest favourite

A spacious kitchen island is highlighted with a wooden tray holding a glass vase filled with vibrant roses. A stainless-steel sink and decorative soap dispensers are visible, while a flat-screen TV displays scenic imagery in the background. Soft natural light brightens the area.

Villa in Slade

5 out of 5 average rating, 49 reviews

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

A grand brick structure with a prominent front facade featuring large white pillars and a central entrance. The property is surrounded by well-maintained green landscaping and a spacious lawn. A hint of historical charm is evident in the architectural design, set against a clear blue sky.

Villa in Paris

4.84 out of 5 average rating, 86 reviews

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.

Guest favourite

A cozy outdoor firepit area is surrounded by Adirondack chairs, arranged in a circle on a gravel surface. Soft, warm lights hang overhead, illuminating the space against a serene, wooded backdrop, creating an inviting atmosphere for gatherings.

Villa in Prospect

4.92 out of 5 average rating, 119 reviews

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.

Superhost

The exterior of a historic home is highlighted, featuring intricate Victorian architecture with decorative trim. A welcoming front porch is visible, adorned with potted plants. The surrounding landscaping includes dark mulch and a clear sky, providing a charming view of the property.

Villa in Lexington

4.86 out of 5 average rating, 65 reviews

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

Guest favourite

A modern cabin exterior is viewed from the front, featuring a large covered porch with two bright yellow chairs. The structure showcases a prominent peaked roof with wooden beams. Clear skies and green grass surround the home, enhancing its welcoming appearance.

Villa in Harrodsburg

4.93 out of 5 average rating, 81 reviews

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.

Guest favourite

A newly constructed villa features a triangular roof and a front porch with wooden railings. Large windows are visible on the upper section, allowing natural light to illuminate the inviting entrance. The surrounding landscape appears lush and green under a clear blue sky.

Villa in Harrodsburg

4.96 out of 5 average rating, 79 reviews

Bourbon Villa at Daynabrook Farm-HOT TUB1

Guest favourite

A modern cabin exterior showcases a combination of dark siding and warm wooden accents. A covered porch features two seating chairs, while a bright orange door invites entry. The surrounding landscape includes grassy fields and a clear blue sky.

Villa in Harrodsburg

4.83 out of 5 average rating, 59 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-4

Superhost

The exterior of a newly constructed villa is showcased, featuring a large front porch with wooden railings and two inviting chairs. The triangular roof design emphasizes the structure's height, complemented by a front door located centrally beneath an overhang.

Villa in Harrodsburg

4.88 out of 5 average rating, 76 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-6

Superhost

A modern A-frame cabin is depicted, showcasing a welcoming porch with two wooden chairs. The structure features a dark exterior complemented by large windows and a distinctive peaked roof. The front door, painted in a soft orange hue, adds a pop of color to the facade.

Villa in Harrodsburg

4.9 out of 5 average rating, 77 reviews

Villa On the Bourbon Trail with HOT TUB-3

Superhost

A newly constructed villa is showcased at night, featuring a striking combination of blue exterior and wooden accents. The inviting porch is illuminated, highlighting decorative seating. A well-maintained lawn surrounds the property, with a small tree adorned in fall foliage positioned nearby.

Villa in Harrodsburg

4.86 out of 5 average rating, 59 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-5

The historic Briar Rose Estate is showcased against a clear blue sky, surrounded by lush, green lawns. The architectural details of the grand house, with its classic columns and multi-pane windows, are highlighted by the gentle slope of the hill.

Villa in Shelbyville

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.