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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, 71 reviews

House w/private pool & hot tub, dogs ok

BetsyRating, 5 stars5 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 stars1 week 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 stars2 months 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, 109 reviews

LexFunZone! Pool! Hottub! GameRm! Cozy Backyard!

CharlesRating, 5 stars4 days ago
We were celebrating a Batchelor weekend … the game room, pool and hot tub, and set up was perfect for what we wanted and did!
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, 15 reviews

Horse Country at The Palm House-Update Ranch home

EileenRating, 5 stars1 month 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 stars1 week 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, 99 reviews

Modern Farmhouse/20 acres/9 miles from Horse Park

BethRating, 5 stars4 days ago
This was a repeat visit for us and as always, we found it exactly what we are looking for at the end of a long day. Most peaceful to sit outside overlooking greenery and pleasant surroundings.

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, 77 reviews

The Cottage

AllisonRating, 5 stars2 weeks ago
We had a wonderful stay at Steve’s house in Midway. The house is SO charming… even more so than the pictures convey. Perfectly outfitted, totally comfy and the perfect location for a fun weekend of Keeneland racing and Midway dining (be sure not to miss Holy Hill Inn and Heirloom for two of the best dining experiences you’ll ever have!). The location is both convenient and beautifully picturesque. Don’t pass this one up! You won’t regret it!
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, 41 reviews

Clean, Convenient, Cozy in Heart of the Bluegrass

RhettRating, 5 stars2 weeks 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!
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, 16 reviews

Cottage in horse country!

DeniseRating, 5 stars3 days ago
We were in town to attend 3 Day Event at Kentucky Horse Park . We enjoyed our stay, loved the porch and comfortable furniture and beds. Kitchen was very well stocked and large dining table allowed for us to all gather for meals and enjoy cards at the end of our day. Being all horse people, we so loved seeing the surrounding farms with mares and their foals. Close by restaurants, Wallace Station and Barrel and Brown were great as well as Midway Bakery for homemade bread and quiche. Hope to return some time!
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!
Home in Versailles
4.92 out of 5 average rating, 13 reviews

Historic Sugar Hill with Pool! Acreage!

ClayreRating, 5 stars3 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
Top guest favorite
The two-story retreat is framed by lush greenery, showcasing a mix of wood and stone exterior. Large windows provide ample natural light, while a modern entryway is highlighted in a vibrant hue. The surrounding yard features well-maintained grass and mature trees.
Home in Lexington
5 out of 5 average rating, 30 reviews

CINDERELLA'S GUEST HOUSE

NicoleRating, 5 stars3 days ago
The place was lovely and everything we expected from the posting. Beautiful natural lighting and homey feel.

Private house rentals

Top guest favorite
A charming cottage exterior is framed by a large tree, with a well-maintained lawn and shrubs lining the front. The entrance features a porch with a welcoming door and matching window shutters, all under a sloped metal roof.
Home in Midway
4.99 out of 5 average rating, 121 reviews

Country Cottage in Horse and Bourbon Country

AlysonRating, 5 stars2 days ago
Third time staying at Mary’s and we couldn’t say enough great things about it! We love coming back year after year
Top guest favorite
A modern living area is showcased with a sleek television, wooden furniture, and a rug. A staircase with wooden steps and metal railings is visible. Through an open space, a dining area with dark chairs and a decorative wall art piece can be seen, enhancing the open layout.
Home in Frankfort
5 out of 5 average rating, 161 reviews

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

MichaelRating, 5 stars2 weeks ago
Wow! This place was awesome! Adam communicated so well, the entire space was spotless. Adam clearly pays a great deal attention to detail and it shows in the games in the house to play, the pristine bathroom and shower, the fire pit in the back with wood supplied and the offer of more. We can’t wait to go back!
Top guest favorite
A welcoming entrance is depicted, featuring a set of wide wooden stairs leading to a black front door. Black railings and modern wall sconces frame the entrance. Large windows on either side of the doorway allow for natural light, enhancing the clean lines of the white brick exterior.
Home in Nicholasville
5 out of 5 average rating, 44 reviews

Keene Cottage mins to Keeneland and Lexington

JohnRating, 5 stars1 week ago
Great place will stay again!
Guest favorite
A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.
Home in Midway
4.99 out of 5 average rating, 82 reviews

The Bees Wing

MadisonRating, 5 stars3 weeks ago
My group had such a great time! Looked exactly like the photos and had so much room! Everything worked great and I loved all the hot water even when we all took showers! There was lots of extras in the pantry like games seasoning cups and plates that were very helpful and a good set of condiments! Such an adorable lace and definitely would stay again next time we go to keen land! It was to cold outside for us the truly enjoy the pool but it looked lovely!
Guest favorite
A charming cottage is set on two acres of land, featuring a wooden deck with steps leading to the entrance. A fire pit and several outdoor seating options are visible in the grassy area. Lush trees surround the property, enhancing the natural setting.
Home in Lawrenceburg
4.99 out of 5 average rating, 70 reviews

Bourbon Barrel Cottages #4 on the Kentucky Bourbon Trail

MeganRating, 5 stars1 month ago
We stayed one night in the cabin on our way home from Gatlinburg. It was the favorite part of our trip! The cabin was beautiful, thoughtfully stocked with everything we could need. Beautiful and secluded surroundings. We will be back for sure!
Top guest favorite
A charming, two-story house is nestled between two large trees, with a wide lawn surrounding it. The home features a porch area and is partially shaded, while warm sunlight casts a long shadow across the grassy yard. A serene, rural setting is highlighted by a wooden fence in the background.
Home in Versailles
4.95 out of 5 average rating, 176 reviews

Quaint little farm house close to Keeneland/horses

GlenRating, 5 stars3 days ago
Cute old farm house in a great location. Well stocked with everything you need.
Guest favorite
Home in Versailles
4.88 out of 5 average rating, 8 reviews

Bourbon Central! Prime Location and Amenities

NatalieRating, 5 stars1 month ago
This house was perfect for us! We had 2 children under 10 with us as well and they loved the house! Well updated and had everything we needed. Definitely recommend!!!
Guest favorite
Home in Frankfort
4.89 out of 5 average rating, 44 reviews

The Field House by Castle & Key

KathleenRating, 5 stars1 week ago
Great location! Beautiful property! Wonderful weekend stay in the Bluegrass state with a short drive to Keeneland!!

Destinations to explore