
Vacation rentals with a pool in Kentucky
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kentucky
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Kentucky rentals with a pool
House rentals with a pool

Close to Everything! Beautiful two-story home
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.

Hillside Retreat Paradise
Ken’s large house had so much space for our big family. The street is quiet and private and the surroundings are beautiful. The house itself had so much to do and was close to everything we planned for our weekend away.

LexFunZone! Pool! Hottub! GameRm! Keeneland/Derby!
The place was exactly as described and had everything we needed (and more!). Harrison responded to any questions immediately and gave us some great recommendations in the area. Thank you, Harrison!!

Hidden Acres Escape: A Bluegrass Retreat
This is an amazing place! I would highly recommend staying here to anyone! We look forward to staying here again

The Bees Wing
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!

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

Maple Place
Overall a positive experience. The interior has been nicely remodeled and was very comfortable for a family of five. The kitchen was well supplied and the hosts were very responsive to our questions.

Game room! 5 beds an 4 bedrooms
The game room was so much fun for the kids staying with our group! They loved the arcade machines.
Condo rentals with a pool

Woodson Bend Gorgeous Lake View Condo First Floor
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.

Relaxing Cumberland Getaway
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.

WoodsonBendResort 7-3 Condo 1 Brd Lake Cumberland
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

Gated Golf Course Condo w/view of Lake Cumberland
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.

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

Lake Cumberland Resort Condo w/ Direct Lake Access
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.

Luxury Apartment/Near Louisville/EV Charger
We stayed at Toni’s place while we were house hunting in the area. The place was beautiful and had everything you needed! We traveled with our 1.5 yr old and there was a great playground a short walk away!

Lovely 3-bedroom lake condo with golf and a pool
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.
Destinations to explore
- Barn rentals Kentucky
- Treehouse rentals Kentucky
- Hotel rentals Kentucky
- Boutique hotel rentals Kentucky
- House rentals Kentucky
- Family-friendly rentals Kentucky
- Rentals with a washer and dryer Kentucky
- Loft rentals Kentucky
- Rentals with an EV charger Kentucky
- Farmstay rentals Kentucky
- Rentals with a sauna Kentucky
- Smoking-friendly rentals Kentucky
- Townhouse rentals Kentucky
- Cottage rentals Kentucky
- Rentals with an accessible height toilet Kentucky
- Rentals with breakfast Kentucky
- Lake house rentals Kentucky
- Private suite rentals Kentucky
- Rentals with beach access Kentucky
- Villa rentals Kentucky
- Rentals with outdoor seating Kentucky
- Rentals with lake access Kentucky
- Rentals with a fireplace Kentucky
- Pet-friendly rentals Kentucky
- Rentals with a patio Kentucky
- Fitness-friendly rentals Kentucky
- Kid-friendly rentals Kentucky
- Condo rentals Kentucky
- Bed and breakfasts Kentucky
- Beachfront rentals Kentucky
- Rentals with a kayak Kentucky
- Guesthouse rentals Kentucky
- Rentals with an accessible height bed Kentucky
- Cabin rentals Kentucky
- Rentals with a hot tub Kentucky
- Apartment rentals Kentucky
- Tiny house rentals Kentucky
- Rentals with a firepit Kentucky
- Waterfront rentals Kentucky
- Rentals with pools 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