Holiday rentals with a pool in Lake Cumberland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lake Cumberland

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Superhost

Apartment in Bronston

4.86 out of 5 average rating, 29 reviews

Lovely 3-bedroom lake condo with golf and a pool

Choose to relax, have fun, or both within this wonderful community with your friends and family! We look forward to welcoming you into our home. - Newly renovated TOP FLOOR condo within a golf cart lake resort - 3 bd 2 ba - Lake access on resort - Private enclosed deck - Pool, golf, volleyball, tennis, pickle ball - Restaurant onsite (closes after summer) - Live music on particular dates - Golf cart rentals - Private boat launch - Boat rentals - Short distance from restaurants, bars, and fun

Guest favourite

Home in Burnside

4.84 out of 5 average rating, 105 reviews

Ohana - Best Views and Best Experiences

One of the best views on the lake nestled in the Daniel Boone National Forest. Spacious 4 BR home w/bonus basement sleeping area w/Queen memory foam mattress. Large hot tub under covered screen porch & located in a private gated resort community w/multiple pools, tennis courts, walking/ATV trails- all within 1 mile of boat ramp. New furniture & TVs in every bedroom, basement game room with bar/poker table, jacuzzi tub in master. Terrific lake views from every room! Excellent WiFi for working.

Guest favourite

Cabin in Burnside

4.89 out of 5 average rating, 18 reviews

Lake Cumberland Resort Getaway

Charming private cottage in a gated Community at Lake Cumberland Resort, this 3-level home sits on 2 acres inside in the Daniel Boone National Forest & has fantastic reviews. Watch the sunrise from the front porch swing & sunsets from the the hot tub patio around the outdoor fire place. Gather around a campfire pit under the stars, or hike over a hundred miles of trails that literally start in your back yard. Active security patrols, three swimming pools, boat ramp, boat dock & tennis courts.

Superhost

Home in Somerset

4.63 out of 5 average rating, 8 reviews

Take It Easy@The Easy Peasy

•Vintage 40's farmhouse w/fabulous private pool (closed for season)+ hot tub area •Centrally-located, 2 min. to boat ramp+ 7 to marina • Hidden speak-easy themed basement bar w/pool + poker tables, shuffle board,+ more (search home for entrance+code) •Equipped country kitchen+sunroom w/drink fridge, games,+ coffee bar. •Unique attic space for family fun (lake house+camp themed w/games+movies) • 5 BR, 2 full baths-1st retro styled w/soaking tub, 2nd w/double sink+walk-in shower • Pet friendly

Guest favourite

Cabin in Burnside

4.84 out of 5 average rating, 37 reviews

Hidden Oasis

This cabin is perfect for your families needs, with a community pool within walking distance, community boat ramp access into Lake Cumberland, hot tub with outdoor tv, cornhole, fire pit, grill, and many more outdoor activities. Inside you can sleep 12 guests and enjoy the perfect family vacation. You can enjoy board games, billiards, watch movies or just relax near the fireplace. Your backyard is the Daniel Boone National Forest lodged in a gated community with 24 hour patrolled security.

Guest favourite

Townhouse in Burnside

4.94 out of 5 average rating, 64 reviews

Lakeside Hideaway I - lakefront w/hot tub

Welcome to our newly renovated lakefront townhouse on Lake Cumberland! Enjoy the view from our spacious decks or relax in the hot tub, by the campfire, or in the community swimming pool. Boaters can access the public boat ramp a quarter mile down the road. Hiking and ATV trails are located in the surrounding Daniel Boone National Forest. Cumberland Falls, Natural Arch, Princess Falls, the Big South Fork Recreation Area, SomerSplash Waterpark, and wineries are located a short drive away.

Guest favourite

Cabin in Burnside

4.92 out of 5 average rating, 63 reviews

Cozy Cabin w/Hot Tub in Lake Cumberland Resort, KY

This cabin backs up to the Daniel Boone National Forest. Located at Lake Cumberland Resort, in Burnside Kentucky, this cabin offers a 3 brm, 2 full bath that sleeps up to 10 people. There are smart tv's in every room, Wifi, 24 Hr gated security, a community pool open from memorial day to labor day, and a boat ramp inside the resort for easy access to the river. Perfect for planning a hiking trip , family reunion, boating adventure , UTV trip, girls/guys trip, or fishing tournament.

Superhost

Cabin in Burnside

4.92 out of 5 average rating, 218 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

Guest suite in Williamsburg

4.95 out of 5 average rating, 197 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

Cabin in Burnside

4.94 out of 5 average rating, 50 reviews

Whispering Woods Cottage | Hot Tub | Pool

Welcome to Whispering Woods, your peaceful sanctuary nestled near Lake Cumberland. Step into our cozy 1-bedroom cottage that offers tranquil surroundings and a restorative night's sleep after your day's adventures. Perfect for a romantic getaway, a solo retreat, or a change of scenery for remote workers, Whispering Woods provides space for up to two guests. ☆ Book your escape at Whispering Woods today to experience the enchantment of lakeside living. Your perfect retreat awaits! ☆

Top guest favourite

Home in Somerset

5 out of 5 average rating, 70 reviews

Spacious Home near Lake Cumberland

This home is BIG (4,700 sq.ft.) with covered porches, shaded pergola, and expansive patio with a fire pit, gas grill and an above ground pool. We’ve just added a game room in our basement! Check out our pictures! A fully stocked kitchen and 4 BIG living areas with big TV's allows room for lots of friends/ family fun. A boat ramp is just down the road! We’re close to town and the lake with parking room for your cars, truck and boat. Come and enjoy our BIG home near the lake!

Guest favourite

Guest house in Williamsburg

4.88 out of 5 average rating, 486 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.