Holiday rentals with a pool in Kentucky

Find and book unique homes with a pool on Airbnb

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Popular amenities for Kentucky rentals with a pool

House rentals with a pool

Guest favourite
Home in Lexington
4.99 out of 5 average rating, 77 reviews

Close to Everything! Beautiful two-story home

JamesRating, 5 stars1 month ago
It was a real home not the usual stuff you see on the apps. 2 fireplaces , huge outdoors and clean as could be. It was a perfect space inside and outside especially for the holidays. Definitely worth it.
Guest favourite
Home in Louisville
5 out of 5 average rating, 17 reviews

Louisville Country Manor - Pool & Pickleball!

ClarissaRating, 5 stars1 month ago
Brandon was a great host. He answered all questions I had and went above and beyond to make us feel comfortable away from home for Christmas. He had a tree and decorated added for the holidays. The house is very spacious and I would definitely recommend to others!
Guest favourite
Home in Newport
4.97 out of 5 average rating, 33 reviews

Hillside Retreat Paradise

RobRating, 5 stars1 month ago
From start to finish my experience with Ken was top tier. The house is beautiful and was perfect for my leadership retreat. My business partners are still talking about it . This is also great for a family getaway.
Superhost
Home in Blaine
4.8 out of 5 average rating, 105 reviews

Hidden Acres Escape: A Bluegrass Retreat

MadinaRating, 5 stars1 month ago
very nice house. Had a great holiday with family
Guest favourite
Home in Midway
4.99 out of 5 average rating, 80 reviews

The Bees Wing

MelanyRating, 5 stars3 months ago
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!
Guest favourite
Home in Georgetown
5 out of 5 average rating, 12 reviews

Horse Country at The Palm House-Update Ranch home

AngieRating, 5 stars2 weeks ago
Jenni’s house was the perfect place to gather, relax and enjoy our family time in KY. Jenni should write a “How To” book for Airbnb hosts! Jenni started communication prior to our arrival which was not only helpful, but made me comfortable if/when I needed to reach out during our stay. Next, not only is this house perfectly decorated (looks exactly like the photos), but it is perfectly appointed as well! I have been to Airbnb’s that either have nothing or the absolute bare minimum with regard to things like, kitchen accessories…even utensils! NOT this house! We made three big dinners during our stay and we had EVERYTHING we needed to cook a full spread each time-there’s an air fryer, a crock pot, frying pans, cookie sheets, baking dishes, oven mitts (yes, I stayed in a house once that did not have oven mitts…and I didn’t even realize it until I needed to take something OUT of the oven). I could go on and on, and would, but I’m out of space. Thank you for an amazing stay!
Guest favourite
Home in Lexington
4.84 out of 5 average rating, 171 reviews

Silver Streak Ranch - Horse Hideaway

HannahRating, 5 stars4 months ago
Loved our stay at Deb’s. Excellent location and tons of amenities! Huge plus for being pet friendly. Our pup felt right at home!
Guest favourite
Home in Stanton
5 out of 5 average rating, 12 reviews

Maple Place

EricaRating, 5 stars3 months ago
We had a great stay! House was beautiful and roomy. We will definitely stay again

Apartment rentals with a pool

Apartment in Bronston
4.83 out of 5 average rating, 6 reviews

Woodson Bend Gorgeous Lake View Condo First Floor

MegRating, 5 stars19 months ago
Woodson Bend is always a great place to be. We love the pool, ability to put your own boat in the water at the resort, the golf and the golf cart community. Debbie’s place is clean, well stocked and as it is shown in the pictures and description.
Guest favourite
Apartment in Bronston
4.98 out of 5 average rating, 41 reviews

Relaxing Cumberland Getaway

JeffreyRating, 5 stars5 months ago
We've been coming to Woodsen Bend for over 30 yrs and have rent too many unit's to remember. Beth's unit is clearly the most comfortable, and well appointed we have ever rented. She has prepared a home away from home. Amazing from A to Z.
Guest favourite
Apartment in Bronston
5 out of 5 average rating, 17 reviews

WoodsonBendResort 7-3 Condo 1 Brd Lake Cumberland

CraigRating, 5 stars4 months ago
Tony’s place was absolutely phenomenal. It was in great condition, we had 4 guys and each had their own spot to sleep comfortably. Absolutely no complaints and already planning a golf trip next year
Guest favourite
Apartment in Bronston
4.89 out of 5 average rating, 81 reviews

Gated Golf Course Condo w/view of Lake Cumberland

ShondaRating, 5 stars4 months ago
This condo was beautifully decorated and very clean. The furniture was very comfortable. The location was great and the area was very peaceful. The owner was super friendly and easy to work with. We were a last minute booking and a late arrival and he was ver accommodating. Will definitely stay her again.
Guest favourite
Apartment in Bronston
4.86 out of 5 average rating, 7 reviews

Amen Corner at Woodson (46-3) Golf Pool Pickleball

ChristineRating, 5 stars7 months ago
We have been going to Woodson Bend since I was a kid. We finally outgrew my parents place and needed a place of our own. We had a great stay at this Condo. We have 4 kids and the bunk beds were great, the condo was clean, and they had very detailed instructions.
Apartment in Bronston
4.75 out of 5 average rating, 20 reviews

Lake Cumberland Resort Condo w/ Direct Lake Access

Jeff Rating, 5 stars8 months ago
Wendy was a great host. We frequent Woodson bend and I will be saving her place as an option in the future. Walk to the pool in less than 5 minutes. The beds were comfortable. Kitchen is fully stocked with everything. You will need to purchase ice as the fridge did not make any, not a big deal since you can get a bag at the guard shack for a few bucks. The only thing I will mention is that I believe owner has a dog so if you have allergies, be mindful of this. My wife dealt with allergies during our stay so she avoided the living room and took Benadryl to help. We were gone most of the day at the pool or on the lake. Overall, nice and peaceful, would recommend.
Guest favourite
Apartment in Crestwood
4.86 out of 5 average rating, 35 reviews

Luxury Apartment/Near Louisville/EV Charger

AmnaRating, 5 stars3 months ago
Very nice and clean space and quiet area . We had a good time staying in there .
Superhost
Apartment in Bronston
4.86 out of 5 average rating, 29 reviews

Lovely 3-bedroom lake condo with golf and a pool

TimRating, 5 stars7 months ago
Enjoyed our stay. Nicely updated condo with plenty of room. Convenient to pool, playground and restaurant. Stools around the kitchen counter instead of table with chairs.

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