House vacation rentals in Woodford County

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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 stars6 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, 80 reviews

Close to Everything! Beautiful two-story home

ScottRating, 5 stars3 weeks ago
We were there for my son’s graduation and this place was perfect for getting the family all in the same place. Wish we were there over the summer to use the swimming pool.
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, 114 reviews

Summer Bliss! Pool&FunZone Oasis! Hottub! GameRm!

GeorgeRating, 5 stars1 week ago
Harrison was an amazing Host! The house was immaculate and had everything you could want to feel at home and relax. This is a premier spot to take your family for Visiting the gorgeous and historic Lexington. Thank you so much for an amazing place to gather as we celebrated our son’s graduation.
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, 86 reviews

The Bees Wing

JohnRating, 5 stars1 day ago
This was our second stay at the Bee’s Wing house. Our group of four felt right at home and enjoyed the location in Midway. The house was very comfortable and reflected a lot of charm. The extra amenities were especially welcome… things you don’t typically find in other homes we’ve rented. The hosts have responded when needed, although we didn’t have any requests for this trip. We would gladly stay again when in the area.
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 stars2 months 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, 97 reviews

Game room! 5 beds an 4 bedrooms

RahminRating, 5 stars3 weeks ago
Jeff's place was in a great central location in Lexington. There is a lot of room in his home, and even has a game room. It was very easy access and I appreciate the flexibility of arrival. He was very easy to communicate as well. I have family in Lexington and coming back for another graduation end of year.. will definitely stay here again
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
4.81 out of 5 average rating, 165 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

JoshRating, 5 stars7 months ago
Overall great stay ! Exactly as described from the hot tub down to the amenities in the house. Very peaceful area and very easy to get to many area attractions! Thank you Joe !
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, 102 reviews

Modern Farmhouse/20 acres/9 miles from Horse Park

JohnRating, 5 stars3 weeks ago
Very peaceful setting! Perfect for a long weekend getaway for UK Graduation.

Weekly house rentals

Top guest favorite
A basement space features a DIY 9-hole putt-putt golf course set against a concrete floor. Green turf outlines various paths and obstacles, while a brick fireplace adds a cozy touch to the room's ambiance. Exposed ceilings with pendant lights enhance the playful atmosphere.
Home in Midway
5 out of 5 average rating, 30 reviews

Stylish & Tranquil ~ Hot Tub ~ Jukebox ~ Mini-Golf

AmyRating, 5 stars2 weeks ago
We had a group of six adults for a Bourbon Trail trip and it was perfect. Great location, clean and fun accommodations, and just right amenities. We were a little worried about all sharing one bathroom, but we took turns and it all worked well. The Jukebox, hot tub, and mini golf were fun touches and it was extremely clean. (I've stayed at many airbnbs, and this one was by far the cleanest!) We would definitely stay here again and would highly recommend it to others!
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, 46 reviews

Keene Cottage mins to Keeneland and Lexington

RebekahRating, 5 stars2 weeks ago
Christian has a wonderful home, full of good little touches, everything comfortable and lovely! Has a kitchen fully stocked with dishes, pots, pans, blender, griddle, almost anything you might need to make and enjoy food. Plenty of towels, thoughtfully provided toiletries. There was a booklet with recommendations for food and things to do in the area, helpful notes for the stay and clear directions for checkout. We enjoyed the game room below - didn't quite get out to using the fire pit but it was such a good He was very communicative and responsive. We had an instance of someone in our party accidentally locking us all out of the house (didn't pay attention to the note of how the lock worked) - upon messaging, they speedily provided resolution to get us back in! And then when we noted to him that a foosball was missing (in an evening), he had one delivered to us by the next morning. I definitely recommend Christian’s hospitality! All in all, a wonderful stay!!
Top guest favorite
A spacious living area features a plush blue sofa and two vibrant yellow chairs. A flat-screen TV is positioned on a white console. Natural light filters through multiple windows, illuminating a decorative area rug placed on the warm wood flooring.
Home in Frankfort
4.93 out of 5 average rating, 70 reviews

Whiskey Woods: Newly Remodeled w/ HOT TUB!

KathleenRating, 5 stars1 day ago
The house and location were wonderful! Our daughter got married at Castle & Key so we were very close to the venue, and the open concept kitchen, dining, and living space were perfect for getting ready and family time. Thank you for helping make a special weekend even better!
Superhost
A two-story home features a welcoming front porch with decorative columns. Lush greenery surrounds the entrance, complemented by manicured landscaping. The wooden exterior displays a blend of dark shingles and light trim, while large windows allow natural light to fill the interior.
Home in Versailles

NEW Sunroom, Downtown, Horse Country, Fireplace

CourtneyRating, 5 stars2 weeks ago
The home was beautiful and in a wonderful location for us needing to get to our event venue. The house was even better than the pictures. Big house and beautifully decorated with high end appliances.
Top guest favorite
A cozy living area features a grey sofa adorned with decorative pillows, accompanied by a patterned armchair. A round floral area rug sits on polished wooden flooring, while an open kitchen area with wooden cabinetry and modern appliances is visible in the background.
Home in Frankfort
4.96 out of 5 average rating, 23 reviews

Bourbon Trail Hideaway

EllieRating, 5 stars3 weeks ago
We really enjoyed this place. Our favorite part was seeing the horses basically right in the backyard! This location is the perfect spot if you are trying to hit different distilleries and it is close to the highway and lots of different restaurants. It was very clean and would defiantly stay again!
Top guest favorite
A spacious dining area is highlighted by a large wooden table surrounded by several chairs. Barn-style sliding doors lead to a well-lit area filled with natural light. A piano and a decorative cabinet are visible along one wall, adding to the inviting atmosphere.
Home in Midway
5 out of 5 average rating, 70 reviews

Midway Cottage-Vineyard, Bourbon Trail, Horses

VanessaRating, 5 stars1 month ago
Our trip to Midway was great, Pamela was awesome. She made us feel at home and gave us some great suggestions! The house was perfect for 3 couples, with separate space. The house was very clean! Midway has some great restaurants and you are very close to Keeneland. Would definitely recommend
Guest favorite
A spacious backyard is bordered by greenery, featuring a stone fire pit surrounded by six light-colored chairs. The elevated house can be seen in the background, with a deck that overlooks the yard, offering a serene view of the surrounding trees.
Home in Versailles
4.97 out of 5 average rating, 62 reviews

Riverside Roost -bourbon themed water front home

LoriRating, 5 stars1 day ago
The home is as described and looks like the pictures . The bunk beds worked well for the grandkids and the room had a tv for them. The living room/great room worked well for the family together . Nice deck in back for family to gather . The home is about a 10 to 15 minute drive to area restaurants , grocery and other activities in the area. The host/manager were very easy to communicate with .
Guest favorite
A scenic view showcases a grand brick house situated atop a rolling hill, framed by lush green grass and a white horse fence. The entrance features elegant brick gates, hinting at the inviting charm of the property.
Home in Frankfort
4.89 out of 5 average rating, 45 reviews

The Field House by Castle & Key

JoelRating, 5 stars3 weeks ago
So blessed to stay at your beautiful place. So relaxing and we all really enjoyed the seclusion and beautiful weather!

Private house rentals

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, 45 reviews

Clean, Convenient, Cozy in Heart of the Bluegrass

KalynRating, 5 stars6 days ago
I had an amazing experience staying at this Airbnb! The place was exactly as described—clean, cozy, and well-equipped with everything I needed. The location was perfect, with a very large backyard Jude was incredibly responsive and welcoming! The photos and description of the place to exactly what you get! I would absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a great stay!
The kitchen features a central island crafted from wooden barrels, complemented by modern stainless steel appliances. Open shelving displays glassware. Light bamboo flooring enhances the space, while a cozy living area with a soft grey sofa and patterned rug is visible in the background.
Home in Midway
5 out of 5 average rating, 25 reviews

Bit and Bourbon

KrisRating, 5 stars25 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!
Guest favorite
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
5 out of 5 average rating, 5 reviews

Eleanor's House

AbbeyRating, 5 stars3 weeks ago
Great place for UK graduation!! Loved it!
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
4.9 out of 5 average rating, 10 reviews

Spacious Frankfort Retreat on Bourbon Trail!

KyleeRating, 5 stars1 month ago
I didn't get to stay myself my husband did with co workers for work and they loved the place and had no complaints
Superhost
The entrance of the duplex features a white door framed by light green shutters. A greeting sign is mounted on the exterior wall beside the door. Planters with decorative greenery are positioned on either side of the entrance, enhancing the welcoming look.
Home in Lexington
4.66 out of 5 average rating, 68 reviews

Silver Streak Retreat

ValerieRating, 5 stars3 weeks ago
We had an amazing stay! It was perfect for the KY Derby weekend! We enjoyed the hosts store and restaurant on the property and the food was good! The house is beautifully decorated with eclectic pieces. The beds were comfortable with luxury bedding. We also enjoyed the sun room for reading. In the spacious backyard, we enjoyed having a pit fire every night despite the rain. The fully stocked coffee bar and s’mores were extra special treats! We would love to stay again!
Guest favorite
A sunroom features a comfortable blue sofa adorned with decorative pillows. Two poufs provide additional seating. Lush plants are placed around the space, while large windows allow natural light to fill the room. Framed botanical prints decorate the white brick walls.
Home in Versailles
4.88 out of 5 average rating, 16 reviews

Historic Sugar Hill Farm w/ Pool! Incredible View!

jenniferRating, 5 stars4 weeks ago
We had a wonderful, memorable vacation that was a lifetime bucket list goal achieved!!! Thank you Anne for giving us a wonderful experience we will always cherish 💖🏇🏻🌹🍾 🥃 🏡!!!!!!
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 stars13 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
A collection of five framed portraits is arranged on a bright green wall. Below, a cozy orange couch is complemented by a textured throw blanket in a gradient of blue and green hues. A wooden coffee table is partially visible, enhancing the warm atmosphere.
Home in Lexington
5 out of 5 average rating, 31 reviews

CINDERELLA'S GUEST HOUSE

NicoleRating, 5 stars1 month ago
The place was lovely and everything we expected from the posting. Beautiful natural lighting and homey feel.

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