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

Cottage in Salvisa

4.97 out of 5 average rating, 120 reviews

Cottage on the Bourbon Trail

Newly built cottage located in the country. Enjoy amazing views from a covered front porch as you rock in comfortable rocking chairs. Fully furnished and beautifully decorated to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a kitchen for cooking if desired. Pool is behind owners residence and is shared with owners family and possibly 2 additional people. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

1–8 Oct

$316 NZD per night

Guest favourite

Guest suite in Lexington

4.95 out of 5 average rating, 216 reviews

Equestrian, Sports Fans, Bourbon Trailers

Great location! Convenient to airport, downtown, UK, great stayover point for bike riders, less than hour to Red River Gorge. 5 minutes to Keeneland Racecourse. Great for business travelers. Private bedroom with queen sized bed, large family room and private bathroom. FUTON in family room area provides additional sleeping space, comfortable for one, tight and cozy for 2. Onsite, off street parking. Enjoy the pool just outside the door! Park like setting in older neighborhood.

20–27 Aug

$219 NZD per night

Guest favourite

Barn in Mount Eden

4.98 out of 5 average rating, 121 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.

4–11 Sep

$229 NZD per night

Guest favourite

Guesthouse in Stanton

4.98 out of 5 average rating, 234 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

27 Jul – 1 Aug

$318 NZD per night

Guest favourite

Cabin in Burnside

4.88 out of 5 average rating, 130 reviews

Cumberland Cabin Get Away

Come and get away! Relaxing cabin backing to the Daniel Boone National forest. Located in the Lake Cumberland Resort. This gated community offers swimming pools, tennis courts, easy boat ramp access, and security. Private setting provided in this cozy cabin is great for a couple and families. Private parking for 2 vehicles, fire pit, large covered back deck with LED lighting, and tons of movies and games for kids. Inside is decorated with antiques and has a great country farmhouse feel.

11–18 Jul

$171 NZD per night

Guest favourite

Cabin in Covington

4.93 out of 5 average rating, 246 reviews

Guest House Monte Cassino Vineyards

The Guest House at Monte Cassino Vineyard, an architectural gem. At 650 sq ft, this free standing, studio loft space is a ground up restoration of an 1830s summer kitchen. Completed for 2016 season, it includes a kitchenette, with mini fridge, microwave and coffee machine. Outdoor grill is available as well. The living room has a fireplace and the bedroom loft is a designer's dream. Adjacent to the main house, the GH also includes use of the pool in season. Extremely private grounds.

14–21 Oct

$297 NZD per night

Guest favourite

Cabin in Burnside

4.92 out of 5 average rating, 184 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!

27 Nov – 4 Dec

$301 NZD per night

Guest favourite

Guesthouse in Williamsburg

4.89 out of 5 average rating, 432 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.

4–11 Oct

$297 NZD per night

Guest favourite

Cottage in Maceo

4.97 out of 5 average rating, 145 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 .

6–13 Aug

$146 NZD per night

Guest favourite

Home in Lynch

4.91 out of 5 average rating, 124 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. Your stay includes a full, home-cooked breakfast. Plenty of parking; can accommodate trailers & RVs.

14–21 Oct

$231 NZD per night

Guest favourite

Cottage in Hopkinsville

4.93 out of 5 average rating, 105 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!

19–26 Sep

$181 NZD per night

Guest favourite

Guest suite in Williamsburg

4.97 out of 5 average rating, 150 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.

24–31 Dec

$193 NZD per night