Holiday 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 favourite

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 favourite

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 favourite

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 favourite

Guest suite in Williamsburg

4.96 out of 5 average rating, 180 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 favourite

Guesthouse in Williamsburg

4.88 out of 5 average rating, 460 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 favourite

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 favourite

Home in McCarr

4.97 out of 5 average rating, 107 reviews

God's Country

Property is a ranch style house with wood siding, nestled against a hillside with a private setting. This property offers a large yard with a in-ground pool as well as a large front porch. There are two patio areas in the back with a built in grill station and a fire-pit to enjoy on those cool evenings. The house boasts six bedrooms, open concept living room, kitchen, and dining room area with gas fireplace, and large family room.Please enter the correct number of guest

Guest favourite

Guesthouse in Lexington

4.93 out of 5 average rating, 194 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 favourite

Cottage in Hopkinsville

4.94 out of 5 average rating, 128 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 favourite

Tiny home in Clay City

4.89 out of 5 average rating, 100 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.

Guest favourite

Home in Lynch

4.92 out of 5 average rating, 145 reviews

Tranquility in the Mountains - House

Peaceful getaway offers relaxation & adventure in the KY mountains. Short drive to VA & TN. Large home has 4 bedrooms - 2 w/ private bath & 2 that share a double-vanity bath. Open living/dining area and kitchen. Nearby is a 7-hole golf course and swimming pool, hiking, and tourist attractions such as Portal 31 and the KY Coalmine Museum, as well as Kingdom Come State Park. Plenty of parking; can accommodate trailers & RVs.