
Vacation rentals in Jessamine County
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Jessamine County
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Jessamine County vacation rentals
Other great vacation rentals in Jessamine County
Top guest favorite

Home in Lexington
4.99 out of 5 average rating, 78 reviewsClose 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
4.91 out of 5 average rating, 22 reviewsMy Old Kentucky Home
RickRating, 5 stars1 week ago
Great place for large family gathering. Communication with the host was excellent. Would definitely come back.
Top guest favorite

Home in Versailles
5 out of 5 average rating, 14 reviewsHome in Versailles on the Bourbon Trail
DebbieRating, 5 starstoday
We cannot say enough about how perfect our stay was. Meghan communicated with us several times before we arrived to m help us plan our trip. lots of tips. when we arrived, the house smelled so clean and was spotless! Everything was perfect. There was a chilled bottle of wine waiting for us. The next morning we had coffee and a variety of creamer . Soap, shampoo ,and conditioner were actually the same products I use at home. Everything about the house was perfect! The bedding was so nice and mattresses were very comfortable. We loved sitting on the porch having our coffee. The day it rained, we sat on the screened porch. Meghan was so gracious and we were invited to meet her horses. It was a treat to see them up close ad learn a bit about their breed and the events they were trained for. Three full baths accommodated our group of four ladies. The setting was just gorgeous. It was very convenient to every place we wanted to go.
Top guest favorite

Farm stay in Lancaster
5 out of 5 average rating, 185 reviewsSerene barn loft in the heart of the Bluegrass
PaigeRating, 5 starstoday
Better than imagined! Peaceful and private. Host is amazing! Answered and questions I have and made the stay very comfortable.
Guest favorite

Home in Lexington
4.94 out of 5 average rating, 16 reviewsElegant spacious 4 BD 3 full bath house!
LeeRating, 5 stars5 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.
Top guest favorite

Home in Lexington
5 out of 5 average rating, 24 reviewsSummit Retreat - 4BR/2.5BA-Keeneland, Airport, UK
BrookeRating, 5 stars6 months ago
My family and I stayed at Scott’s house while we were in town to see the races at Keeneland. The house was clean and had everything we needed. It was a 20 min drive to the racetrack and about an hour and 15 min from sdf airport. No complaints, comfortable beds.
Top guest favorite

Vacation home in Nicholasville
5 out of 5 average rating, 14 reviewsStone & Cedar Lodge - pool, hot tub, fire pit, EV
CindyRating, 5 stars1 week ago
Sam was fantastic, helpful friendly and quick to respond. Helped my husband when he needed a tool for the vehicle. The house was fabulous with all the space needed for our family. Large yard which was perfect for our Easter egg hunt. The house had more amenities than any other such as supplies, dishes, and cookware. Lots of beach towels for the pool 🙂. We will definitely return. Thank you Sam for being a great host!
Guest favorite

Barn in Nicholasville
4.93 out of 5 average rating, 101 reviewsThe Barn Loft
LizRating, 5 stars6 months ago
It’s hard to believe this place is real!! Coming from Boston to this beautiful, peaceful property was just what we needed. I think my favorite part was rocking in a rocking chair watching the horses graze and play. 10/10!!! We will definitely stay here again! ( also was very comfortable, had everything we needed and was very clean) Thanks for having us!
Destinations to explore
- Apartment rentals Jessamine County
- Kid-friendly rentals Jessamine County
- Rentals with breakfast Jessamine County
- Rentals with a hot tub Jessamine County
- Rentals with lake access Jessamine County
- Rentals with a fireplace Jessamine County
- Rentals with a patio Jessamine County
- Rentals with pools Jessamine County
- House rentals Jessamine County
- Rentals with a fire pit Jessamine County
- Pet-friendly rentals Jessamine County
- Rentals with a washer and dryer Jessamine County
- Townhouse rentals Jessamine County
- Rentals with outdoor seating Jessamine County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes