Vacation rentals with a pool in Shelby County

The “Derby Winner” was a wonderful and fitting home for our stay. 4 bedrooms—all with king size beds—was perfect for our group of four adults. The outdoor space and amenities were exactly what we were looking for, as well. It was a very comfortable and relaxing space. Tony & Danielle are amazing hosts and we’re always responsive to our needs and requests. Would absolutely recommend this home for anyone looking for a nice stay!

My family and I had an incredible Christmas experience at this wonderful place! The pictures and descriptions were impressive, but being there in person was truly amazing. Our host, Kaeley, was exceptional with communication and accommodations. She graciously allowed us to check in early, which was a huge help since we were traveling from out of state. The house was fully stocked with amenities, and the kids had an absolute blast playing games in the spacious barn! We also enjoyed quality time in the Bourbon Room, surrounded by beautiful and comfortable furniture. The home's decorations were impeccable. We would definitely visit again! Thank you, Kaeley, for creating such an unforgettable experience for my family and me.

This is a great place to stay, peaceful and quiet! Pool, hot tub, and bar came in handy when relaxing The margarita maker was clutch lol Dustin is always responsive when needed!

We loved this Victorian home full of character! The beds were comfortable as were the gathering room couches. (Yes a new loveseat not shown in the pictures). The back porch was perfect for relaxing any time of the day and we used the table out there for meals too. We sat in the back yard to stargaze. The kitchen was extremely well stocked!! It is just delightful when a host/hostess takes the “B and B” part of this traditionally - with some breakfast items available! SO nice! 😊 We had some trouble with the shared bathroom not draining but were able to get it resolved. Great communication with our hosts! We loved the location- one block off the main strip of shops and restaurants in Midway! And as stated 15 - 20 mins to at least 3 distilleries, more cute shops in Versailles and to Keenland. Only about 30 mins into Lexington. Just perfect!

Loved our stay at Deb’s. Excellent location and tons of amenities! Huge plus for being pet friendly. Our pup felt right at home!

We stayed at the Holiday House in July so it was hot in Kentucky. The pool/hot tub and shade trees came in handy. We had a group of 8-9 people and the house was well stocked with a chef’s kitchen and every utensil and kitchen appliance. Host also provided coffee which was nice. The surroundings are idyllic and beautiful. You are nestled into the rolling Kentucky hills but you can feel the quiet yet historical nature of the place. Lexington is a quick 20 min drive. We enjoyed grabbing breakfast sandwiches and scones from the Midway Bakery (located inside an old school). Lots of Gluten Free options on the menu. There is convenience store and fast food a few minutes away and Midway/Lexington has a decent variety of restaurants. The host suggested the local winery which was nice and had local music/wine on the weekend. Golf and horses nearby. Our party was a mix of age groups and everyone felt right at home. The hosts were very attentive and friendly. Highly recommended!

Absolutely perfect! I would say this AirBnb is one of the best that we’ve stayed at. Amazing views of the river. Kristen was very responsive and had everything we needed at the house. The kitchen was stocked with everything you need to cook meals. Beds were comfortable and there were plenty of towels and hot water! I definitely recommend Kristen’s house! I know I didn’t want to leave!

Beautiful home, quiet area, just what we needed for our weekend getaway. We would stay here again