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Villa vacation rentals in Kentucky

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Top-rated villa rentals in Kentucky

Guests agree: these villas are highly rated for location, cleanliness, and more.

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A tranquil swimming pool is illuminated under soft lighting, showcasing two yellow inflatable ducks floating on the water. Surrounding the pool are inviting seating areas, with a large umbrella providing shade, and a backdrop of the white fence and house, creating a serene outdoor retreat.

Villa in Brandenburg

5 out of 5 average rating, 14 reviews

Historic Estate, Pool, Hot Tub, Group Retreats

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.

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.

5 out of 5 average rating, 46 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.

4.85 out of 5 average rating, 84 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.

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

4.93 out of 5 average rating, 115 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.

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

4.92 out of 5 average rating, 64 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

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

4.92 out of 5 average rating, 79 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.

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

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.

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

4.89 out of 5 average rating, 76 reviews

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.

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, 58 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-5

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.

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

New place to stay

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.

Top guest favorite

The exterior of a ranch-style home is displayed under a twilight sky, showcasing a snow-covered landscape. Soft illumination highlights the entrance, while the nearby hills create a serene backdrop. The overall atmosphere conveys a sense of peace and seclusion in a quiet setting.

Villa in Stanton

4.96 out of 5 average rating, 115 reviews

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.

A collection of four houses is displayed, nestled among greenery and mature trees in a valley setting. The main house features distinct architectural lines and a welcoming porch, while the cottages exhibit charming brick exteriors, each set within landscaped grounds.

Villa in Harlan

5 out of 5 average rating, 4 reviews

Appalachian Downtown Harlan KY 4 Guest Houses

We are going above and beyond for our private homes! Everything washable will be sanitized washed and cleaned with bleach or disinfectant. Vela's Villa is a private little neighborhood within a neighborhood–a group of 4 houses sharing the same lot, located a block away from historic downtown. Nestled in a valley in the ancient & enchanted Appalachian mountains! Wifi

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Kentucky villa rentals

Free parking on premises

Air conditioning

Private villa rentals

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

4.92 out of 5 average rating, 79 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-2

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

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

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

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

4.89 out of 5 average rating, 76 reviews

Villa On the Bourbon Trail with HOT TUB-3

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

4.93 out of 5 average rating, 115 reviews

Bourbon Trail, Firepit

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, 58 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-5

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

4.92 out of 5 average rating, 64 reviews

National historical home in the Heart of Lexington

Luxury villa rentals

A collection of four houses is displayed, nestled among greenery and mature trees in a valley setting. The main house features distinct architectural lines and a welcoming porch, while the cottages exhibit charming brick exteriors, each set within landscaped grounds.

Villa in Harlan

5 out of 5 average rating, 4 reviews

Appalachian Downtown Harlan KY 4 Guest Houses

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

4.92 out of 5 average rating, 64 reviews

National historical home in the Heart of Lexington

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

New place to stay

Historic Briar Rose Estate | Sleeps 16 |

A tranquil swimming pool is illuminated under soft lighting, showcasing two yellow inflatable ducks floating on the water. Surrounding the pool are inviting seating areas, with a large umbrella providing shade, and a backdrop of the white fence and house, creating a serene outdoor retreat.

Villa in Brandenburg

5 out of 5 average rating, 14 reviews

Historic Estate, Pool, Hot Tub, Group Retreats

Villa rentals with a pool

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

New place to stay

Historic Briar Rose Estate | Sleeps 16 |

A serene swimming pool is framed by well-maintained green lawn and landscaping. Black wrought-iron chairs are positioned nearby. Lounge areas are shaded by pergolas, and decorative planters complement the outdoor space under a bright blue sky with scattered clouds.

4.85 out of 5 average rating, 84 reviews

Barr House Inn-historic 18 miles to LexKY/HorsePK

Top guest favorite

The exterior of a ranch-style home is displayed under a twilight sky, showcasing a snow-covered landscape. Soft illumination highlights the entrance, while the nearby hills create a serene backdrop. The overall atmosphere conveys a sense of peace and seclusion in a quiet setting.

Villa in Stanton

4.96 out of 5 average rating, 115 reviews

Red River Gorge. Pool. Pets. Wi-fi

The room features a spacious bed with light linens positioned against an orange accent wall. Natural light enters through a large window draped with red curtains. Wall-mounted lamps provide soft illumination, and a small bedside table is visible.

Villa in Owensboro

New place to stay

Motel 6 Owensboro, Ky_1 Queen Bed | Ada/

A tranquil swimming pool is illuminated under soft lighting, showcasing two yellow inflatable ducks floating on the water. Surrounding the pool are inviting seating areas, with a large umbrella providing shade, and a backdrop of the white fence and house, creating a serene outdoor retreat.

Villa in Brandenburg

5 out of 5 average rating, 14 reviews

Historic Estate, Pool, Hot Tub, Group Retreats

Destinations to explore