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House vacation rentals in Woodford County

Find and book unique houses on Airbnb

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Popular amenities for Woodford County house rentals

House rentals with a pool

Top guest favorite
An inviting heated pool is surrounded by manicured landscaping, featuring tall grasses and colorful plantings. A water slide adds a playful element, and shaded areas are provided by large umbrellas. The pool's clear blue water reflects the bright sunlight.
Home in Lexington
5 out of 5 average rating, 70 reviews

House w/private pool & hot tub, dogs ok

BetsyRating, 5 stars4 months ago
Better than expected. Fantastic and well-stocked kitchen - everything we needed for a full Thanksgiving feast. So many thoughtful details for a comfortable stay. Hot tub and backyard were awesome. Nice walkable neighborhood. Close to all things horses and handy to downtown. Highly recommend and will definitely stay again when in town.
Top guest favorite
Home in Lexington
4.99 out of 5 average rating, 78 reviews

Close to Everything! Beautiful two-story home

LukeRating, 5 stars4 days ago
Kathy’s home is the perfect place to stay. We had plenty of room, a lot of amenities. The outdoor space was fantastic. We felt welcomed and right at home and I would book with Kathy anytime I visit the area in the future. The home is gorgeous and in a safe neighborhood. I highly recommend this property for your next trip to Lexington.
Superhost
A welcoming entryway is framed by lush greenery and flowering plants. A concrete path leads to the front door, which features large glass panels. Potted plants are positioned on either side of the entrance, adding a touch of nature to the inviting approach.
Home in Lexington
4.72 out of 5 average rating, 39 reviews

Private for 4 No cleaning fee Discounts up to 20%

JordannRating, 5 stars1 month ago
Overall, a great 2-week stay! Sherrie was friendly, responsive and helpful. The unit was spacious, comfortable and beautiful...home-like, tidy and well-decorated. It was a little challenging to work with the unusual "kitchen" setup for the duration of my time, but I was able to make it work with Sherrie's help. (there is a full-sized fridge, a mini fridge, 2 microwaves and a well-functioning hot plate...there is just no kitchen sink... Sherrie helped me by doing my dishes for me a number of times and was very easygoing about offering that help). This place is very cute and comfortable - NOT bare-bones, like you sometimes get on here. Definitely would recommend and would stay here again!
Top guest favorite
A bright and inviting outdoor area features a refreshing swimming pool with clear blue water. Surrounding the pool are sun loungers and a shaded gazebo, set against a backdrop of lush trees and well-maintained landscaping.
Home in Lexington
4.96 out of 5 average rating, 108 reviews

LexFunZone! Pool! Hottub! GameRm! Cozy Backyard!

AudreyRating, 5 stars3 weeks ago
Loved my stay here. Harrison is a great host and the house is a perfect place to relax at after a long day. Lots of space for big groups too!
Top guest favorite
A refreshing in-ground pool is surrounded by a wooden deck and lounge chairs, offering a perfect spot for relaxation. Lush greenery lines the property, and seating areas with umbrellas provide shaded spaces for gathering. The exterior of the home features large windows that invite natural light.
Home in Georgetown
5 out of 5 average rating, 14 reviews

Horse Country at The Palm House-Update Ranch home

EileenRating, 5 stars3 weeks ago
This house is fantastic. Comfortable beds, extremely clean, stocked kitchen utensils, and great instructions for everything in the house. This is a very nice neighborhood and we felt extremely safe. Close to restaurants and shopping. The house exceeded our expectations.
Top guest favorite
A refreshing pool is surrounded by a wooden deck, featuring lounge chairs and a table with an umbrella. Floating toys are visible in the clear water, while lush greenery and trees provide a natural backdrop to the inviting outdoor space.
Home in Lexington
5 out of 5 average rating, 95 reviews

Game room! 5 beds an 4 bedrooms

AbbeyRating, 5 stars4 days ago
This place was perfect for a stay of me and my friends. It’s clean and exactly as described. Thank you, Jeff!
Superhost
A dual-level deck houses an above-ground swimming pool with clear blue water. Two custom wooden chairs provide seating near the pool's edge, framed by a brown fence and lush greenery in the background. The deck surface is finished in light grey, enhancing the outdoor space.
Home in Lawrenceburg
4.82 out of 5 average rating, 162 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

RobertRating, 5 stars6 months ago
It was perfect for our needs. Very clean and close to 3 distilleries. The kitchen is well stocked with pots pans bakewear etc, and clean. bedrooms and baths are clean and comfortable. The hot tub and pool were clean and ready for us with plenty of space outside to sit and relax. over all it was a great location and very well taken care of.
Top guest favorite
An open-concept living area features high ceilings supported by dark beams. A comfortable sofa and a rug are positioned on the wood floor, while a kitchen with colorful bar stools is visible in the background. Large windows allow natural light to fill the space.
Home in Georgetown
4.98 out of 5 average rating, 98 reviews

Modern Farmhouse/20 acres/9 miles from Horse Park

MaraRating, 5 stars3 weeks ago
We thoroughly enjoyed our stay. The area is beautiful and convenient to nearby restaurants and shopping. The house was tastefully decorated with high end finishes and quality linens. The kitchen was equipped with everything imaginable for cooking. There was plenty of room and privacy for us three married couples traveling together. Will definitely stay again when we return to the area!

Weekly house rentals

Top guest favorite
A spacious kitchen is highlighted by wooden beams and a mix of modern and rustic elements. White cabinets contrast with the wooden dining table and bar stools. Natural light is welcomed through large windows, enhancing the inviting atmosphere of the area.
Home in Midway
4.96 out of 5 average rating, 76 reviews

The Cottage

IanRating, 5 stars2 weeks ago
Overall great stay. Steve is very responsive and helpful. He provided great local recommendations. The house is well maintained and very clean. The back porch is a great area to sit and relax at the end of the day. Will stay again.
The historic home features a yellow exterior with subtle white trim, outlined by mature trees and manicured shrubs. A wide brick pathway leads to the front entrance, accentuated by a spacious porch with several windows and decorative elements. The two-story structure embodies classic architectural charm.
Home in Versailles
5 out of 5 average rating, 3 reviews

Near Keeneland and on Bourbon Trail Lexington area

JaniceRating, 5 stars1 month ago
Great place to stay, close to things to see. We went to Wallace Station for lunch and it was great only 6 miles from the house. Easy to get there.
Top guest favorite
A modern living area features a sleek fireplace beneath a mounted television. Natural light fills the space through large windows. A wooden coffee table is placed in front, adorned with candles and a remote, while textured sofas offer comfortable seating.
Home in Versailles
4.98 out of 5 average rating, 40 reviews

Clean, Convenient, Cozy in Heart of the Bluegrass

RhettRating, 5 stars1 week ago
This was our second time staying at Jude’s for a Keeneland weekend. Super close to the races and an absolutely wonderful Airbnb. It’s clean, comfortable, has excellent amenities and walking distance from the Versailles Brewery. The Bose sound system is great for music and dancing. We will definitely be staying here again in October for another racing season. Highly recommend for anyone staying in the Lexington area!
Home in Wilmore
4.92 out of 5 average rating, 13 reviews

The Hardin House

AllisonRating, 5 stars9 months ago
William’s home was the perfect vacation spot! Quiet and peaceful! We spent most of our time in the pool or sitting outside with our dogs. With the fenced in yard, it made it so easy to have them out there with us. William was extremely responsive to any questions we had. House was very clean and very welcoming! We hope to be back sometime soon!
A charming brick pathway leads to the entrance, bordered by lush green ferns in hanging planters. Colorful flower arrangements are prominently displayed, while a wooden railing guides the way up to the home. The inviting atmosphere is subtly enhanced by natural light filtering through the trees.
Home in Midway
5 out of 5 average rating, 25 reviews

Bit and Bourbon

KrisRating, 5 stars23 months ago
Great place to stay if you are in town for Bourbon, wine and horses! Host gave us great recommendations on places to visit and eat. They had all the essentials for us. Less than a block away from downtown Midway with plenty of great places to eat. Will definitely be back!
A cozy living area is highlighted by a soft sectional sofa arranged around a wooden coffee table. A stone fireplace serves as the focal point, complemented by a flat-screen TV mounted above. Large windows allow natural light to fill the space, enhancing its inviting feel.
Home in Frankfort
4.88 out of 5 average rating, 8 reviews

Spacious Frankfort Retreat on Bourbon Trail!

SarahRating, 5 stars1 month ago
Howard was very responsive and got our questions answered quickly. The home was just as described and very nice! We had a great stay and felt right at home the entire weekend! They had everything we needed in the kitchen and more. We would definitely stay here again! Thank you!
Home in Versailles
4.92 out of 5 average rating, 13 reviews

Historic Sugar Hill with Pool! Acreage!

ClayreRating, 5 stars2 weeks ago
Our stay at Anne’s was perfect! She was very responsive and accommodating from the moment we booked, through check out. The property was exactly as described.; cozy and comfy! The location was ideal for our family to stay during opening weekend of Keenland. Short drive to the track and town. The country setting is gorgeous and very private. Overall, we couldn’t have asked for a better place to stay. Highly recommend! We will definitely return.
A charming farmhouse is framed by lush green pastures and a rustic black wooden fence. Trees dot the landscape, providing natural beauty against a cloudy sky. A gravel path leads up to the house, enhancing the inviting rural setting.
Home in Lexington
4.89 out of 5 average rating, 18 reviews

Malcomb Farm

ConnieRating, 5 stars12 months ago
We LOVE this home! I was there on business and my tram and myself stay at this home and it was the perfect place to come back to after a busy day! The host was wondereful and helpful! We even say horses in the field across the way

Private house rentals

The exterior of a one-story home is shown, featuring a welcoming front porch with steps and wooden railings. A well-maintained lawn surrounds the property, complemented by neatly arranged shrubs. Clear skies enhance the visibility of the home's facade.
Home in Wilmore
New place to stay

Eleanor's House

JacquieRating, 5 stars1 month ago
This place was perfect for a family of 2 adults and 4 children 2-14 to stay at. They had the perfect accommodations for everyone from toys to a heated blanket! The home was cozy and wonderfully decorated and the perfect size for our family on our weekend getaway, thanks for letting us stay!
An expansive outdoor area is visible, featuring a grassy lawn scattered with fallen leaves. In the background, a red barn stands against a cloudy sky, with a hedge marking the border of the property.
Home in Midway
4.64 out of 5 average rating, 11 reviews

Midway Home on 22 Acres Near Bourbon Trail!

DianaRating, 5 stars10 months ago
Loved the house! The convenience of getting to distillery was great. The rooms were awesome.The microwave had problems and the can opener needs to be replaced . But other than that it was perfect
The living room is designed with a comfortable leather sofa and two armchairs arranged around a coffee table. Light streams in through the windows, adorned with blue drapes. A decorative plant adds a touch of nature, complementing the neutral tones of the space.
Home in Versailles
4.64 out of 5 average rating, 55 reviews

Farm Cottage- Views! Horses!

ToshaRating, 5 stars1 week ago
we live the Jockey Suite and was perfect for my Keeneland Birthday weekend. The house was exactly like the pictures showed and Anne was an amazing hostess. Would definitely rent rent this house again. Bonus with seeing all the baby horses and Mamas in the field right next to the house. close to Keeneland and downtown Versailles.
A bright and welcoming living area is adorned with a leather sofa and a wooden coffee table. A large flat-screen TV is mounted on the wall, while natural light streams through the window, illuminating the room. A door leads to the entrance.
Home in Wilmore
4.67 out of 5 average rating, 3 reviews

15 Mi to Dtwn Lexington: Serene Wilmore Home!

LaurenRating, 5 stars42 months ago
The furnishings at this home were really nice, and the beds comfy. We enjoyed sitting on the front porch and chatting as well as hanging out in the cozy living room and kitchen space. Thanks for offering such a well appointed home near the bourbon trail!
Top guest favorite
A spacious living area features a comfortable leather sofa with patterned throw pillows, complemented by a round coffee table. Nearby, a dining table accommodates four, and large windows provide natural light, showcasing a serene outdoor view. The decor includes earthy tones and textures.
Home in Midway
5 out of 5 average rating, 15 reviews

Cottage in horse country!

KyleRating, 5 stars1 week ago
What a wonderful home! It is obvious that great attention to detail was paid to the design, furnishings, technology, interior design, and decorating. The host, Andrea, was very prompt and flexible with our needs. Our friends were wowed, as they had never stayed in an Air BnB, and this cottage was a great first impression.

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