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.

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Guest favorite

Barn in Mount Eden

4.99 out of 5 average rating, 143 reviews

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs are welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

Guest favorite

Guesthouse in Stanton

4.98 out of 5 average rating, 268 reviews

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

Superhost

Cabin in Burnside

4.91 out of 5 average rating, 206 reviews

The Enchanted Hideaway /Pet Friendly with Hot Tub!

Come relax at the Enchanted Hideaway Cabin just minutes from beautiful Lake Cumberland within the gated Lake Cumberland Resort. This 2 BR 2BA cabin offers much to love including open concept kitchen, dining, and living room area, washer and dryer, screened-in porches, grill, fire pit and much more! And you will love the private hot tub on the back porch! There are 3 community swimming pools in the resort with one only a short walk from the cabin. Book your perfect get-a-way today!

Guest favorite

Home in Benton

4.91 out of 5 average rating, 171 reviews

Country Charm❤️Ky Lake Area*2BR*Kit*LR*Bath

You'll have COMPLETE privacy in the walk-out basement apt-(lower floor only) of our upscale safe & quiet neighborhood. NOTE it’s COLD: 67-68 when we run the AC & you CAN'T change the TEMP that's set on 70. Explore our 1.5 wooded acres with pool (seasonal)swing set & fire pit. Watch the hummingbirds finches hawks & eagles! Guests love our king & queen beds, plush linens, 50"TV & stocked kitchen. Your comfort is my priority! May allow a dog>40lbs with pre-approval & pet fee $40.

Guest favorite

Guest suite in Williamsburg

4.96 out of 5 average rating, 181 reviews

Creekside Adventures

Make some memories at this unique and family-friendly place. Our guest suite is very spacious and open. Many of our guest have let us know how inviting and relaxing it is to stay in. We also have a creek where our children use to play when they were little. Kids can easily play in it when the weather is nice but please be careful on the walls and stones. We also have a pool area that is available for swimming during late May through early September. We do not allow pets. No Parties

Guest favorite

Guesthouse in Williamsburg

4.88 out of 5 average rating, 461 reviews

Williamsburg Poolside Homestead

Private guest house with incredible outdoor resort feel, nature, and simple homestead life. 3 miles to University of the Cumberlands. 20 min to Cumberland Falls, home of the world's only Moonbow. *NO smoking of any kind (e-cig included) permitted anywhere on the property or the entire neighborhood. Guests violating our smoking policy are subject to a minimum $400 fee for returning the house or property to smoke-free status and agree to being charged by accepting this policy.

Guest favorite

Cottage in Maceo

4.97 out of 5 average rating, 157 reviews

Hattie's Hill Cottage

Cottage sits behind our home (see photo) . NOTE- Main house may have large groups ... pool and outside areas share spaces ...Near Owensboro, Rockport, Hawesville & Lewisport...There is ONLY ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi ..Smart TV... use your Netflix and so on with this TV ...... Kitchen has everything you need ..Eating/work space. Comfortable recliner chairs ... Use of pool/ plenty of places to roam on farm .

Guest favorite

Guesthouse in Lexington

4.93 out of 5 average rating, 195 reviews

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

Guest favorite

Cottage in Hopkinsville

4.94 out of 5 average rating, 129 reviews

*Pool*Animals*Farm Views*Quaint Cottage

Cute cottage located behind the 100-year-old main farmhouse! This unique 4 acre property boasts gorgeous farmland views, flourishing gardens, and farm animals. You can visit the goats, dogs, and chickens. Enjoy a full kitchen, living and dining area, bedroom, and bath with oversized tub. HUGE fenced saltwater pool with high dive available seasonally! Only 10 minutes to Fort Campbell, Clarksville or Hopkinsville! Also available to host special events! See details!

Guest favorite

Tiny home in Clay City

4.89 out of 5 average rating, 101 reviews

Secluded 2 bedroom cabin w/pool and hot tub access

Enjoy the sounds of nature when you stay in this unique place. Secluded, cozy tiny cabin!! Located in the middle of 37 acres. Gate access! Close to Red River Gorge, Natural Bridge, Kentucky Dragway and kayaking. Private pool and hot tub access! Wi-Fi, Cornhole, grill, deck, fire pit, pond for fishing. Completely furnished…. Everything you could want! I raise Australian shepherd so there are four on the property. They are very friendly and love Airbnb guest.

Superhost

Cabin in Burnside

4.89 out of 5 average rating, 122 reviews

Cozy Hillside Cabin

Beautiful home in Daniel Boone National Forest, surrounded by woods in gated Lake Cumberland Resort about 12 miles from Somerset, KY and just 1 mile to the boat ramp. Each of the 3 BR have their own full bath and TV. There are 2 living areas and full kitchen/eat-in. Home has a wrap around deck with a screen in rear porch. Free high speed Wi-Fi. Fire pit. 4 vehicles parking. ATV trails and 3 pools in the Resort. $100 cleaning fee.

Guest favorite

Farm stay in Harrodsburg

4.95 out of 5 average rating, 136 reviews

The Bunkhouse at Big Red Stables

There is no better way to experience Kentucky than horseback riding the rolling hills of the Bluegrass. Big Red Stables is happy to offer the Bunkhouse to visitors who want to ride horses, travel to nearby bourbon distilleries, go to the races or events at the Kentucky Horse Park, or just get away from it all on a third generation family farm. Horseback riding by appointment only as arranged with your hosts.