House vacation rentals in Jessamine County

Find and book unique houses on Airbnb

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Popular amenities for Jessamine County house rentals

House rentals with a pool

Top guest favorite
Home in Lexington
5 out of 5 average rating, 71 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 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
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!
Guest favorite
Home in Midway
4.99 out of 5 average rating, 82 reviews

The Bees Wing

MadisonRating, 5 stars2 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!
Superhost
Home in Richmond
5 out of 5 average rating, 3 reviews

Heart of Richmond

WilverRating, 5 stars1 week ago
Great place. Would definitely stay again.
Top guest favorite
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
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.
Superhost
Home in Georgetown
4.89 out of 5 average rating, 27 reviews

26 acre farm sleeps up to 30

AdamRating, 5 stars4 weeks ago
Will be our first place to check if ever visiting Kentucky again. Great space

Weekly house rentals

Top guest favorite
Home in Lexington
4.97 out of 5 average rating, 35 reviews

Charming Lexington Townhouse

KinRating, 5 starstoday
We’ve stayed at a bunch of Airbnbs in Lex, and this is one of our favorites. Much bigger than the pictures, huge basement with bunk beds and large tv so the kids can have their own space. Great kitchen and adjoining sun room. Nice bathrooms. Very close to restaurants and shops on Richmond Rd and Hamburg. We used Shamrocks restaurant, the Local Bean for coffee, and Kroger all under a mile away. Neighborhood was very quiet and safe. Will definitely stay here again!
Superhost
Home in Lexington
4.82 out of 5 average rating, 83 reviews

Peggy's Home With Cozy Sunroom

BryanRating, 5 stars2 weeks ago
Great place. Our group felt right at home and was perfect for our weekend stay in Lexington. Peggy was a great host and was very pleasant and easy to contact.
Home in Lancaster
4.99 out of 5 average rating, 69 reviews

‘Our Lakeside Retreat’ w/ Deck on Lake Herrington!

MimiRating, 5 stars4 months ago
The home was perfect for our family. It was very clean, updated, and comfortable. The loft was great for our two grandchildren. It was too cold to use the deck but it was very large and could easily accommodate all eight of us.
Top guest favorite
Home in Lexington
5 out of 5 average rating, 21 reviews

Bluegrass Subourbon Suite & Backyard Oasis

CoreyRating, 5 starstoday
We had a nice stay at this property—Ryan was super responsive and helpful throughout. The location was fantastic, and we really appreciated the thoughtful amenities and the fact that there were minimal checkout chores, which made things easy. Be warned if you stay here, this is a basement within someone's house. I think the listing was a bit misleading. We were expecting a disconnected suite or a whole mini-house based on the description, but this is a basement unit within someone’s home. Ryan owns a dog, so we occasionally heard barking and frequent claws across hardwood upstairs. The suite does have its own entrance through the backyard and the interior door to the upstairs remained locked the entire time, but it was initially a bit jarring. Once we settled in, though, everything was clean, comfortable, and well-equipped, and we still enjoyed our time there.
Guest favorite
Home in Lexington
4.93 out of 5 average rating, 122 reviews

Convenient to Keeneland, airport, food, shopping

CassandraRating, 5 stars1 month ago
was a very beautiful place to stay it was nice very easy to find and Ellen was a great host!! if I need to have a place again I will definitely be booking this place
Guest favorite
Home in Lancaster
4.93 out of 5 average rating, 76 reviews

the Brink

BrianRating, 5 stars5 months ago
Outstanding! some of the best scenic views in the state. The pictures don’t do the view of the palisades justice. One of the coolest rentals I’ve ever been to. We launched kayaks and had the fox river basically to our selves. We had a great experience
Top guest favorite
Home in Lexington
4.96 out of 5 average rating, 77 reviews

Minutes to Keeneland/Airport/UK & more!

AshlynRating, 5 stars3 weeks ago
Katherine was amazing!! She helped me book this last minute for our family and was very responsive the entire time if we needed anything. The house was so nice and had very very comfortable beds. It was very clean and cutely decorated. It definitely felt like a home away from home for us!
Home in Lexington
4.7 out of 5 average rating, 10 reviews

Close to Keeneland, downtown - 3 Bed, 2 Full Bath

JasonRating, 5 stars6 months ago
Everything was as expected and perfect for our needs!

Private house rentals

Guest favorite
Home in Lexington
5 out of 5 average rating, 5 reviews

Camelot Nights

JoeRating, 5 stars1 week ago
Blake’s place was great for our stay. The beds were comfortable and everything was very accommodating. He was a very responsive host with great communication!
Home in Nicholasville
4.67 out of 5 average rating, 3 reviews

Granite State Collection's 9BR 7BA in Bourbon Coun

PeterRating, 5 stars3 months ago
From start to finish, this was a fantastic stay. Angela's team proactively reached out the day prior with details and was responsive to questions throughout. For as good as the team was, the accommodations were even better. There was more than enough room for our team to congregate and then go our own ways to have separate space. Lots of character in the house and it has everything you need.
Home in Nicholasville
5 out of 5 average rating, 10 reviews

Central to Horses, Bourbon & Fun. 10 Min to Lex

JuliaRating, 5 stars1 week ago
Everything was amazing. We stayed here for Keeneland and a concert. Host was super friendly and helpful and responds quickly. Beautiful home! Nicholasville is great very peaceful and pretty neighborhood with a cute park. Only issues were it was about 20 mins to keeneland and 25 to campus so a little further out and the living room doesn’t have curtains so it’s a little exposed at night/watching TV. But overall, great stay!
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!
Guest favorite
Home in Lexington
5 out of 5 average rating, 8 reviews

The Celestial Serenity

KathrynRating, 5 stars1 month ago
The house was as depicted in the photos. The owners were very responsive to a minor issue we had upon arrival and took care of it asap. The kitchen was well-stocked and we were able to cook the few meals that we had planned at home. But-the house was chopped up & the main shared space was very small. The bed/bath layout was odd (trundle bed w/full bath, but king bed with no bath attached) & I felt like Allyson was not terribly helpful when I tried to ask questions about it pre-stay. The decor is in desperate need of an update with many “dust catchers”, statues & artificial vines. There also seemed to be a lot of extra, unnecessary, cluttery furniture pieces. The photos make the property look like it’s in a bit of a secluded area, but it’s right in the middle of a subdivision, which was fine, just a bit misleading. Coffee maker was listed as "drip", but there was also a Keurig, which would have been nice to know. Value for the price was great, but the house was definitely quirky.
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!
Guest favorite
Home in Lexington
4.88 out of 5 average rating, 64 reviews

Cozy 2-bedroom Home Designed for Travelers Alike

VivianRating, 5 stars3 weeks ago
My friend and I stayed at Jordan’s place while we were in Lexington for Road to the Horse. The location made it easy to drive to the Kentucky Horse Park each day. There are no shortages of restaurants and stores in the area so that was a real benefit or us. The neighborhood was walkable so we were able to get some exercise during our time away. Thanks for a great stay.

Destinations to explore