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
4.99 out of 5 average rating, 81 reviews

Close to Everything! Beautiful two-story home

BernardRating, 5 stars1 week ago
This home and it's surroundings are absolutely beautiful! We had a family vacation and had a wonderful time! The pool was amazing and each room of the house was modern and elegant at the same time. Our grandchildren also loved watching the ducks in the little creek. We usually go to the ocean but were looking for something a little closer to home this year (3 hours away) and we were certainly not disappointed! We highly recommend it and will be back some day! Thank you, Kathy! Benson & Diane Bedel & Family
Superhost
Home in Lexington
4.63 out of 5 average rating, 43 reviews

Private for 4 No cleaning fee Discounts up to 20%

CaseyRating, 5 stars1 month ago
This was a great spot for a quick trip! We were visiting for UK's commencement ceremony and this location was close to downtown and very convenient. I would have preferred if I could control the AC/heat, but the weather was nice so it wasn't a big deal. I would definitely stay again!
Guest favorite
Home in Lexington
4.93 out of 5 average rating, 27 reviews

My Old Kentucky Home

JacobRating, 5 stars3 weeks ago
My Old Kentucky Home hosted by Shane was a wonderful place to stay! The neighborhood was beautiful and quiet. The amenities on site were amazing. The hot tub and pool were all set and ready for our group when we arrived, which we appreciated greatly. Communication was great, and Shane was on top of everything. Our stay was wonderful and we would love to come back for another visit! Would recommend to anyone looking to stay in the Lexington area.
Guest favorite
Home in Midway
4.99 out of 5 average rating, 88 reviews

The Bees Wing

JessieRating, 5 stars3 days ago
We went for a girls weekend it was the perfect get away! The screened on in porch was our save haven for the weekend . So peaceful and loved walked to downtown areas .
Guest favorite
Home in Richmond
5 out of 5 average rating, 10 reviews

Heart of Richmond

VanitraRating, 5 stars2 days ago
This Airbnb was definitely more than I could have imagined. Very clean, very comfortable, very homey. Kitchen has everything you could possibly need. Safe for small children. I loved everything about this house. Sherri was wonderful as well. Very fast response time. Very respectful and reasonable. Will be booking again in the near future.
Top guest favorite
Home in Lexington
5 out of 5 average rating, 102 reviews

Game room! 5 beds an 4 bedrooms

StephanieRating, 5 stars1 week ago
This place was very nice and Jeff was a terrific host! Perfect for a nice family getaway. Close to everything. If you are looking for fun and relaxation, this is the house. Game room was a huge bonus with 2 arcade games and several board games. The backyard is so cute, private and cozy. Kitchen was stocked with coffee and everything you need and the beds were comfy. This is a must stay. Very cute house! Loved it!
Superhost
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 !
Guest favorite
Home in Georgetown
4.91 out of 5 average rating, 32 reviews

26 acre farm sleeps up to 30

JoeRating, 5 stars2 weeks ago
Larry was easy to work with and quick to respond. The home was beautiful and perfect for our large group.

Weekly house rentals

Top guest favorite
Home in Lexington
4.97 out of 5 average rating, 37 reviews

Charming Lexington Townhouse

ScottRating, 5 stars1 week ago
The place was great with a ton of room and quick access to plenty of food options nearby!
Top guest favorite
Home in Harrodsburg
4.95 out of 5 average rating, 96 reviews

Lux Lake Gem w/ hot tub

DamianRating, 5 stars5 days ago
Anessa’s place was fantastic. Her kitchen had everything needed for multiple nights of cooking. The area was amazing and the lake was fantastic. We truly enjoyed the space and would love to stay again in the future. The little touches were great. Truly a gem to find.
Guest favorite
Home in Lexington
5 out of 5 average rating, 7 reviews

Camelot Nights

AnnaRating, 5 stars3 weeks ago
Stayed at Blake’s while I was in town for a wedding. This location is close to lots of restaurants and fun things for the kids to do! Blake was very responsive when I reached out to him. Definitely recommend his place.
Home in Lexington
5 out of 5 average rating, 3 reviews

Home in Lexington

MichaelRating, 5 stars1 month ago
Nice place, lots of extras and personnel touches. Would stay here again.
Guest favorite
Home in Lexington
4.82 out of 5 average rating, 17 reviews

Elegant spacious 4 BD 3 full bath house!

LeeRating, 5 stars7 months ago
Great location for a quick Lexington weekend! It was perfect for our crew. Plenty of room and parking. Flexible check-in and check-out. Owner very responsive.
Guest favorite
Home in Wilmore
5 out of 5 average rating, 8 reviews

Eleanor's House

RachelRating, 5 stars1 week ago
Stayed at this beautiful home with my bridesmaids the night before my wedding! The home looked exactly like the pictures and it was so beautiful in person. We had a quiet and peaceful stay. The home is located right outside the quaint little town of Wilmore, KY. Beautiful views, and a short drive into Lexington or surrounding counties for activities. The beds were comfortable, plenty of towels, a little coffee bar, and comfy seating for us to sit a chat for the evening. The home was very clean. Dustin owns able to accommodate an early check in for us. We did have a touch of trouble with the keypad at check in but he was quick to respond and remedy the issue. I would absolutely recommend this home for any family and friends coming to the area to visit.
Guest favorite
Home in Lexington
5 out of 5 average rating, 8 reviews

Southside Charmer with king bed.

NinaRating, 5 stars12 months ago
Laura was responsive and made sure we had everything we need. Kids had fun with the video games. No complaints!
Home in Nicholasville
New place to stay

Historic & Spacious Family Home in Nicholasville!

KhanhRating, 5 stars1 month ago
Beautiful home with lots of character. Totally worth the stay.

Private house rentals

Top guest favorite
Home in Nicholasville
5 out of 5 average rating, 51 reviews

Cliff House

DavidRating, 5 stars1 week ago
The Cliff House is a wonderful house that has many amenities. We loved the environment, the spaciousness, the pool. The kitchen has everything we needed. We had a wonderful stay. It requires a drive to anywhere. Angela was very responsive and provided suggestions when asked. Very helpful!
Guest favorite
Home in Lexington
5 out of 5 average rating, 11 reviews

2 bedroom Cozy & Welcoming Condo

JadenRating, 5 stars2 months ago
Very great home, was very clean and perfect all around for our stay!
Guest favorite
Home in Nicholasville
5 out of 5 average rating, 5 reviews

The McGuire House

JoeyRating, 5 stars1 month ago
This is a great location. Extremely nice and will look to stay again.
Home in Lexington
5 out of 5 average rating, 10 reviews

The Celestial Serenity

LauraRating, 5 stars1 month ago
It was a perfect location for our family. The location is not far from restaurants and the wedding venue that we were attending for the weekend. The house was perfect for everyone. The weather was not so great so we did not get to enjoy the backyard, but it is a very peaceful and beautiful place.
Home in Lexington
4.75 out of 5 average rating, 12 reviews

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

ErinRating, 5 stars1 month 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.
Top guest favorite
Home in Lexington
5 out of 5 average rating, 31 reviews

Bright and Open Two Story House

yullyRating, 5 stars1 week ago
By far the best Airbnb we’ve been to! Everything was very clean, conveniently organized, beautifully decorated and the beds were comfortable. Natalie prepared some snacks and a bottle of wine for us that we got to enjoy on our last night. Kids loved having children’s books and board games that kept them away from the screen. Check in and check out was also very easy. She didn’t require to have anything done but just enjoy the stay! Our trip was short but very sweet thanks to Natalie. If we come back to Lexington, we know where to stay.
Guest favorite
Home in Lexington
4.9 out of 5 average rating, 181 reviews

Pool | Hot Tub | Covered Porch | Patio | Game Room

ShannonRating, 5 stars4 days ago
Lovely home in a quiet neighborhood. We had a group of seven and dogs. There was plenty of room and the large beds throughout were perfect for a group of adults. The creek in the back was so pretty. Our dogs played in it every day. The park behind the house was a nice plus and an easy walk to go play some pickleball/tennis. Since we as renters depend on reviews and everyone has different standards, I will mention a couple of things that could be improved on. I still left 5 stars because for us it didn’t affect our great time. The outdoor cushions need a good cleaning or replacement as they are badly stained. It was obvious that the back deck had not been blown off in a while. A better lawn service company is probably all that’s needed. All in all it is a great place to stay with a large group. Seth was very responsive, accommodating, and friendly. Someone even secretly came to take the garbage bins to the road and put them back. LOL Nice touch.
Home in Nicholasville

Country Villa

JamesRating, 5 stars10 months ago
Our family had a wonderful time enjoying the pool, the privacy, and the beautiful country location of the property. The home was very clean and was well-stocked with everything that we needed. The outside area for grilling out and relaxing was the best. Maureen always responded quickly to any questions that we had. We could not have asked for anything more and look forward to coming back again. Thanks for sharing your home with us.

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