Holiday rentals with a pool in Lake Cumberland

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.

The Bass Shack

Beautiful Golf & Lake retreat located on the 7th hole within Woodson Bend Resort. This is a gated community with 24 hr security, located on a 455 acre peninsula, surrounded by scenic Lake Cumberland. Amenities include a clubhouse with swimming pool (seasonal), tennis, pickleball, and basketball courts. 18 Hole golf course, 3 mile walking trail, playground, restaurant (seasonal), & boat launch. This condo is newly renovated and includes 2 bedrooms, 1 full bath, fully equipped kitchen & laundry.

Lake Cumberland Resort Getaway at the Cabin

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.

Lake-Front Woodson Bend 14-1

1st Floor condo sits on a gorgeous Lake Cumberland. 3-5 minutes walk to the clubhouse, which features a restaurant, swimming pool, kiddie pool, 6 dedicated Pickleball Courts, 2 tennis courts, basketball, volleyball, and playground. Well-appointed kitchen with stainless appliances features a bar area perfect for entertaining! The screened-in heated and cooled back porch w/lake views and a gas grill. The Primary bedroom has a king-size bed and Bedroom 2-Queen and Bedroom 3-Queen w/twin trundle.

Gidget at Villager Resort-Pool,Boat slip/dock

Have fun with the whole family at this stylish place. Gidget is located inside Villager Resort on Lake Cumberland that is a community of about 20 houses. While staying with us you have access to the pool and boat dock. You can take the steps down to the dock or bring quarters and use the tram to take you and your belongings down to the boat dock. The area is very relaxed! We have a tennis/pickleball (bring your own gear) court on site as well as a quarter op arcade area, basketball, fire-pit.

Burnside Bungalow, w/ dock, pool & firepit

Experience a perfect lake getaway at Burnside Bungalow. This newly renovated 3-bedroom, 3-bathroom Lake Cumberland home sleeps 12 and offers views of the lake. The guests have exclusive access to a private dock slip and Villager Resort amenities. The home has an eat-in kitchen, Roku TV, Wi-Fi, and ample parking for vehicles. Enjoy lawn games, S’mores at the fire pit, and the lower level game and bunk room. Check-in time is 4 pm, and check-out time is 10 am. Smoking and pets are not allowed.

Woodson Bend Resort Golf/Pool/Pickleball and More!

Welcome to your perfect getaway! This beautifully decorated rustic condo sits directly across from the swimming pool, on-site restaurant, and tennis/pickleball courts, all within a stunning resort community centered around an 18-hole championship golf course. Step outside and you’re just moments from the volleyball and basketball courts, plus a nearby playground—making this an ideal spot for couples, golfers, families, and adventure-seekers alike. The perfect home base for your getaway!

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.

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.

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!.

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! ☆

Gated Golf Course Condo w/view of Lake Cumberland

Our condo is located on a 400 acre peninsula surrounded by Lake Cumberland. Gated community with 18 hole golf course, swimming pool, sand volleyball, full outside basketball court, tennis courts, pickle ball courts, workout room, library, restaurant, 3 mile road track for those who like to run or walk with a view of Lake Cumberland. Condo has Wifi and Roku tv's. Our condo is located straight across from the pool with a view of Lake Cumberland within a short walking distance.