
Pet-friendly vacation rentals in Jessamine County
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Top-rated pet-friendly home rentals in Jessamine County
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Popular amenities for Jessamine County pet-friendly home rentals
Pet-friendly house rentals

Woodford Stables / Walk to Eckert's Orchard
We had to evacuate our home due to the floods and having to fur babies we had to find a safe place to accept us all. Emily was able to accept us right in with no problems. This house was so beautiful, extremely CLEAN and the location was so peaceful. In what was such a stressful time in our life, we were able to just relax and find peace in her home! We would recommend this stay to anyone! There was plenty of room, a huge yard for our pups to run around and every dish needed to cook with.

Home in Versailles on the Bourbon Trail
What a wonderful experience staying at this property and working with Meghan. The house was beautiful, clean and convenient to Keeneland and a number of distilleries. The property is breathtaking with easy access. Meghan made us feel welcome with detailed instructions and a bottle of wine waiting in the fridge. She made excellent recommendations for restaurants in the area and we loved each one! We had the opportunity to meet her and her beautiful Dutch Warmblood horses while there. Her gracious hospitlity is unmatched! We will be back!

My Old Kentucky Home
We would definitely stay here again. The place was beautiful, and had everything you could want or need.

Elegant spacious 4 BD 3 full bath house!
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.

The Blue Heron Lakeside Chalet
My husband and I and another couple stayed at The Blue Heron for a long weekend, hoping to get some golf in. Shelly was helpful prior to our arrival with grocery and dinner suggestions. We were able to find the place with no problems and had easy access to get in. Very quiet location. Did not see anyone the entire stay. The main house was the perfect size for 4 people. Living room/kitchen provided enough space for us all to be together. The deck would have be great space with the fire pit and outdoor seating. We just happened to come during a 4 day nonstop rain. Which did make for great sleeping. The boathouse provided space for the couple we came with. It had a queen bed, small sitting area bathroom and a great view. The main house had a great loft for the other bedroom. The bed and pillows were amazing. Although we did not get one round of golf in, we did find fun things to do in Lexington. It was very relaxing and we look forward to coming back when the weather is better/warmer.

Lovely Modern House ~Piano/Downtown/Airport
Me and my family had a great stay at Kates place. We had some little issues, but it was taken care of right away!

Endless Summer Lakeside Oasis & Boat Rental
Anessas property at lake Herrington was everything we hoped for! Well stocked with things you don’t always see at other short term rentals but always need. Very convenient, cozy and spacious even for a group of 8 to 10. We felt lucky booking this specific property and made some memories there. Anessas communication was top notch, the property was very clean and well thought out. We would definitely book again!

Sky Beauty/12min to Keeneland/18min to Rupp Arena
Such a gem! This was a great place to pause for a few days with our fur babies and check out the bourbon trail! Comfortable and cozy with great amenities. We would stay again!
Pet-friendly home rentals with a pool

House w/private pool & hot tub, dogs ok
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.

Cozy Cottage on Horse Farm
Christine's guest home is very unique and cozy space. It is located on a working horse farm and has a big pool and hot tub for guest use. Christine was a very responsive and accommodating host, she was always around and responsive. I travel to the area often to visit family and I will definitely be staying here again!

The Nook at Castaway Farm
Lovely,lovely, lovely. Sharon’s place was a perfect retreat for my husband and I. The surroundings are beautiful! We loved spending time with the horses and walking around the property. Lots of local restaurants nearby and EVERYONE is so friendly! Thanks, Sharon, for offering such a perfect place!

The Hardin House
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!

Rest. Recreation. Retreat
We had an amazing stay! Super clean, and felt like it was home away from home. Michael and his wife are outstanding people, and the hospitality and generosity is something that you don’t get along with most Airbnbs. We will be back for a next time!

Historic Sugar Hill with Pool! Acreage!
Our stay at Anne’s was perfect! She was very responsive and accommodating from the moment we booked, through check out. The property was exactly as described.; cozy and comfy! The location was ideal for our family to stay during opening weekend of Keenland. Short drive to the track and town. The country setting is gorgeous and very private. Overall, we couldn’t have asked for a better place to stay. Highly recommend! We will definitely return.

26 acre farm sleeps up to 30
The home was beautiful and plenty of space for our large group. Location was great, private, quiet and close to many places. Would totally recommend for large groups

Modern Farmhouse/20 acres/9 miles from Horse Park
We thoroughly enjoyed our stay. The area is beautiful and convenient to nearby restaurants and shopping. The house was tastefully decorated with high end finishes and quality linens. The kitchen was equipped with everything imaginable for cooking. There was plenty of room and privacy for us three married couples traveling together. Will definitely stay again when we return to the area!
Private, pet-friendly home rentals

Heart of the Bluegrass in SW Lexington
this house is beautiful with lots of space comfortable beds very clean & smelled very nice neighbors where friendly we stayed for Thanksgiving it was very to see the neighborhood kids be inclusive to our kids they played basketball & just enjoyed each other anything I may thought I needed in the home after looking around it was provided he also let us check in a few hours earlier because of the holiday so we could get the food into the house I will definitely rent here again.

Lakeshore escape! "Lake view"
I enjoyed my stay here. Host was very friendly and flexible with my checkin/out. Very private, on the marina, lake view. Small curvy one lane road to get back to it though. The bed could use a new mattress. Otherwise, this place was great! 5 stars would stay again!

Lux Lake Gem w/ hot tub
This was our second stay and it may have been better than the first. Our family couldn't wait for this return trip and it was so relaxing and peaceful. My son is a huge fan of the hot tub and I love that we could bring the doggo with us! The house is beautifully decotared and homey. And I've never had a rental with so many amenities and a kitchen so well stocked!

Highbridge River Cabin, Private Dock, EV Charger
Anna’s home is beautiful! The pictures don’t do it justice. The location is perfect for a peaceful getaway on the River, where you can relax and be around nature. We can’t wait to return for a longer stay in the near future.
Destinations to explore
- Rentals with outdoor seating Jessamine County
- Rentals with a fireplace Jessamine County
- Rentals with breakfast Jessamine County
- Rentals with a fire pit Jessamine County
- Rentals with a hot tub Jessamine County
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- Rentals with a washer and dryer Jessamine County
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- Family-friendly rentals Jessamine County
- Kid-friendly rentals Jessamine County
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- Rentals with pools Jessamine County
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