House holiday rentals in Jessamine County

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Popular amenities for house rentals in Jessamine County

House rentals with a pool

Top guest favourite
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 favourite
Home in Lexington
4.99 out of 5 average rating, 78 reviews

Close to Everything! Beautiful two-story home

LukeRating, 5 stars3 weeks 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 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!
Guest favourite
Home in Midway
4.99 out of 5 average rating, 82 reviews

The Bees Wing

MadisonRating, 5 stars1 month 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!
Top guest favourite
Home in Lexington
5 out of 5 average rating, 96 reviews

Game room! 5 beds an 4 bedrooms

PaulRating, 5 stars1 week ago
Jeff was a great host. Great suggestions before we even asked for any. Place was just as described and perfect for our needs. Would gladly stay here again.
Top guest favourite
Home in Richmond
5 out of 5 average rating, 5 reviews

Heart of Richmond

MitchellRating, 5 stars2 weeks ago
Awesome place to stay! Close to downtown Richmond and very cozy! Beautiful home! We definitely recommend and would stay again!!
Superhost
Home in Lawrenceburg
4.81 out of 5 average rating, 164 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 favourite
Home in Georgetown
4.98 out of 5 average rating, 100 reviews

Modern Farmhouse/20 acres/9 miles from Horse Park

BethRating, 5 stars2 weeks 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

Superhost
Home in Lexington
4.82 out of 5 average rating, 84 reviews

Peggy's Home With Cozy Sunroom

JanelleRating, 5 stars2 weeks ago
Peggy home was quiet and clean and perfect for a small family with a baby attending a horse show at the Kentucky Horse Park. Peggy is welcoming and responsive. Would stay again!
Top guest favourite
Home in Lexington
5 out of 5 average rating, 21 reviews

Bluegrass Subourbon Suite & Backyard Oasis

CoreyRating, 5 stars2 weeks ago
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 favourite
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
Superhost
Home in Lancaster
4.92 out of 5 average rating, 77 reviews

the Brink

BrianRating, 5 stars6 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 favourite
Home in Lexington
4.96 out of 5 average rating, 78 reviews

Minutes to Keeneland/Airport/UK & more!

MarianneRating, 5 stars2 weeks ago
I cannot think of one complaint - Katherine’s home was easy to find and access, spotless and as advertised. The beds were very comfortable, the neighborhood was quiet and we thoroughly enjoyed our stay!
Guest favourite
Home in Harrodsburg
4.91 out of 5 average rating, 91 reviews

Endless Summer Lakeside Oasis & Boat Rental

ChristineRating, 5 stars2 weeks ago
We had a wonderful stay. The house was very clean and smelled good upon arrival. Beds were VERY comfortable and bedding super soft. The giant walk-in shower in the big bedroom was the bomb with the oversized shower head. We really liked the screened-in porch (with a tv!) The property was private and quiet. We are older folks who didn’t attempt the very steep stairs to the water, but the view was great from the deck. We enjoyed antique shopping in Danville and Harrodsburg. Cattleman’s, Drakes and the Red Rooster were all good restaurants. An over all great stay!
Guest favourite
Home in Nicholasville
5 out of 5 average rating, 21 reviews

13mi to Keeneland/C&K Property/ Historic Farm

KathleenRating, 5 stars2 weeks ago
Absolutely gorgeous home! Better than the pictures, even. Easy to find, but still felt so secluded on the beautiful land. Lots of great amenities and touches!
Home in Lexington
4.73 out of 5 average rating, 11 reviews

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

ErinRating, 5 stars2 weeks ago
Melinda’s place was exactly what we needed for our stay for the Kentucky 3day event at the KY horse park. It was very clean, easy to access, as described, and Melinda was very responsive and helpful when my hair dryer caused a fuse to blow in the bathroom. She had someone out immediately to fix it and followed up with me when it was fixed. I felt really bad about it but she was so nice and understanding. The early check in time and late check out time made us feel very at ease, knowing we weren’t in a rush to get out, with 5 adults and a baby in tow! Great place, would love to come back next year.

Private house rentals

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

Charming Lexington Townhouse

KinRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Lexington
5 out of 5 average rating, 5 reviews

Camelot Nights

JoeRating, 5 stars3 weeks 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, 12 reviews

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

TimothyRating, 5 stars2 weeks ago
The house was beautiful and spacious. Rooms were cozy and beds were comfortable. My only gripe was there were no paper towels in the kitchen, no coffee filters, coffee, cream or sugar. Not a big deal but something that would be nice to know in advance. Nothing that was make or break, still 5 stars because the home was immaculate and exceeded expectations in every other way.
Home in Lexington
5 out of 5 average rating, 9 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.
Guest favourite
Home in Lexington
4.86 out of 5 average rating, 65 reviews

Cozy 2-bedroom Home Designed for Travelers Alike

VivianRating, 5 stars1 month 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.
Home in Wilmore
5 out of 5 average rating, 4 reviews

Eleanor's House

JosephRating, 5 stars1 week ago
Wonderful stay....house was very clean and well stocked. Looked exactly like the pictures. Would definitely stay again.

Destinations to explore