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Villa vacation rentals in Lexington

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Top-rated villa rentals in Lexington

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

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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, 81 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.

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, 60 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

4.93 out of 5 average rating, 72 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, 54 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.

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

4.91 out of 5 average rating, 70 reviews

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.

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

4.93 out of 5 average rating, 68 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

4.85 out of 5 average rating, 54 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.

Villa in Lexington

4.95 out of 5 average rating, 39 reviews

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!

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, 103 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 book our Private pool 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.

Top guest favorite

The A-frame house, surrounded by lush greenery, showcases a large deck and stone chimney. Colorful planters hang from the deck railing, and a spacious lawn offers ample space for outdoor activities. A rustic shed is visible to the left, blending harmoniously with the natural surroundings.

Villa in Irvine

4.99 out of 5 average rating, 68 reviews

A-frame house/fishing pond/firepit/sauna & gym

ABOUT OUR HOME Our cozy A-frame house with country decor offers you the perfect place to connect with nature and relax. As you walk trough the deck pay attention to our favorite friends, the hummingbirds! and if you are lucky enough you may also see the deers and turkeys that wander through our property.

Vacation rentals for every style

Get the amount of space that is right for you

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Quaint homes, peaceful surroundings

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Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Lexington 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

4.93 out of 5 average rating, 72 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-2

Villa in Lexington

4.95 out of 5 average rating, 39 reviews

12acre Villa right by Keeneland-Keene Creek Estate

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, 81 reviews

Barr House Inn-historic 18 miles to LexKY/HorsePK

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, 54 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

4.91 out of 5 average rating, 70 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

4.93 out of 5 average rating, 68 reviews

Villa On the Bourbon Trail with HOT TUB-3

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

4.85 out of 5 average rating, 54 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, 60 reviews

National historical home in the Heart of Lexington

Villa rentals with a hot tub

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, 72 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-2

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

4.85 out of 5 average rating, 54 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, 60 reviews

National historical home in the Heart of Lexington

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, 54 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

4.91 out of 5 average rating, 70 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

4.93 out of 5 average rating, 68 reviews

Villa On the Bourbon Trail with HOT TUB-3

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