Villa vacation rentals in Kentucky

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Top-rated villa rentals in Kentucky

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Guest favorite

Villa in Slade

5.0 out of 5 average rating, 18 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

Mar 1 – 8

G$75,592 GYD per night

Guest favorite

Villa in Prospect

4.97 out of 5 average rating, 64 reviews

Bourbon Trail, 150th Derby 2024, Hot Tub, 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.

Aug 12 – 19

G$69,485 GYD per night

Superhost

Villa in Paris

4.87 out of 5 average rating, 76 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.

Apr 29 – May 6

G$69,908 GYD per night

Villa in Louisville

5.0 out of 5 average rating, 3 reviews

Eclectic and Warm Vibe- You will love it!

KENTUCKY DERBY LISTING The property is 2.1 miles from Churchill Downs; a direct route to the track's door. You will see the love in the details here. Every room has a smart tv, santized remotes and access to wi fi. You will have multiple charging stations at your finger tips. Extra pillows and a water cooler are available. There is a Kentucky Derby backdrop set up to take photos. You will love the private parking area and the country porch swing. The space was designed with you in mind.

May 30 – Jun 6

G$72,032 GYD per night

Superhost

Villa in Louisville

New place to stay

~Gorgeous & Spacious Villa ~ Prime Old Louisville~

Discover a haven of tranquility in our completely renovated cottage, where every detail whispers luxury and comfort. Wrapped in the warm embrace of exposed brick walls, the cottage's soulful character merges with an award-winning high-end design. The living space is thoughtfully furnished to provide a cozy yet elegant ambiance. And a spa-like bathroom designed to offer a rejuvenating experience with its sophistication and serene decor. Perfect for small families, couples or single travelers

Mar 29 – Apr 5

G$38,564 GYD per night

Guest favorite

Villa in Lebanon

4.95 out of 5 average rating, 59 reviews

Ticky's Cottage at Empire Estate

Enjoy all the amenities (for booked guest use only, no friends or relatives), such as an inground pool (open May-Sept., 8 a.m.-10 p.m.), 4 manicured acres to roam, sand volleyball/badminton court (open 8 a.m.-8 p.m.), fire pit/picnic area (open 8 a.m.-11 p.m.) next to a stream, horseshoes and more, all located within 50 minutes of major Kentucky Bourbon Trail distilleries. This is a genuine Bourbon Country getaway spot for comfort and serenity but with plenty of fun just minutes away.

Jan 10 – 17

G$27,633 GYD per night

Superhost

Villa in Bowling Green

4.84 out of 5 average rating, 165 reviews

Spacious Countryview Villa - Near WKU and Downtown

The Countryview Villa is a secluded 4500 square feet home, situated on 3 1/2 acres of land with 11 acres of wooded trees behind. We’re a quick 8 minutes from downtown Bowling Green, making it the ideal location for a getaway while still being close to the city and everything else (Walmart, Liquor Barn, Greenwood Mall, Corvette Museum, Lost River Cave and many more). It’s the ideal place for family vacations, reunions, corporate retreats or any occasion to get away from it all.

Nov 11 – 18

G$70,722 GYD per night

Guest favorite

Villa in Lexington

4.96 out of 5 average rating, 26 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!

Feb 27 – Mar 6

G$135,295 GYD per night

Guest favorite

Villa in Stanton

4.94 out of 5 average rating, 68 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.

Dec 31 – Jan 7

G$60,969 GYD per night

Room in Burlington

5.0 out of 5 average rating, 3 reviews

Your home away from your house!

🏡 Welcome to Your Home Away From Home! Experience comfort and convenience in our spacious and well-appointed house located in a safe and serene neighborhood. Perfect for extended stays, we offer two beautifully furnished rooms in a welcoming atmosphere. 🌟Whether you’re in town for work, relocating, or simply exploring the area, our home provides the ideal base for your stay. Experience the comforts of a home away from home, where convenience meets relaxation.

Dec 29 – Jan 5

G$11,056 GYD per night

Guest favorite

Villa in Irvine

4.98 out of 5 average rating, 40 reviews

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

ABOUT OUR HOME Be amazed with the magical reflection of the sunset from our private pond or with a starry night while you share delicious marshmallows in our fire pit. 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.

Nov 2 – 9

G$63,436 GYD per night

Guest favorite

Villa in Harrodsburg

4.95 out of 5 average rating, 44 reviews

Bourbon Villa at Daynabrook Farm with HOT TUB-2

Enjoy convenience mixed with beautiful scenery in this newly constructed villa on the Bourbon trail. This space features 1 bedroom with a King bed, a loft with a Queen bed, pull out sofa, full kitchen, 1 full bathroom, in-unit laundry, and hot tub. Located on a private farm on HWY 127, and just minutes from the Bluegrass Parkway, Keeneland, Shakertown, Herrington Lake, Four Roses Distillery, and the Bluegrass Airport.

Oct 4 – 11

G$48,573 GYD per night