Holiday rentals with a pool in Lake Cumberland

5 out of 5 average rating, 11 reviews

Home in Monticello

Cumberland Belle Lakehouse-5bedrm,10bed,5bath

Perfect space for your get together or event! 5 Bedrooms, 5 Attached Baths, 10 Beds. Sleeps 20 easily. New SwimSpa (large hot tub/ small lap pool)! Entire 2nd floor unit. 2 large decks. Plenty of parking. 2 gas grills and a fire pit. Must be comfortable with STAIRS as this is a second floor unit. ***There is a separate listing to rent the entire home if more space is needed. This would add 4 additional bedrooms (10 beds) 2 more bathrooms, a full kitchen, dining table for 20 and access to sauna

4.81 out of 5 average rating, 91 reviews

Charming Get-A-Way (11C) Fun, Lake, Golf carts

Welcome to Charming Get-A-Way – Your Ultimate Escape! Discover Serenity in Daniel Boone National Forest Escape to the peaceful surroundings of the Daniel Boone National Forest with Charming Get-A-Way, an enchanting 2-bedroom 2.5-bath that offers the perfect haven for relaxation. Situated just a short stroll from the resort’s pool, this home is ideal for families, friends, or a tranquil retreat, blending comfort with nature’s beauty. Equipped with a detached bunkhouse that's perfect for summer.

4.89 out of 5 average rating, 19 reviews

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.

4.83 out of 5 average rating, 23 reviews

Home in Somerset

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.

4.86 out of 5 average rating, 42 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.

4.93 out of 5 average rating, 70 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.

4.9 out of 5 average rating, 232 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 suite in Williamsburg

4.96 out of 5 average rating, 214 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

4.88 out of 5 average rating, 67 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! ☆

4.87 out of 5 average rating, 53 reviews

Townhouse in Burnside

Lakeside Hideaway II - lakefront w/hot tub

Welcome to our rustic lakefront townhome 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.

4.83 out of 5 average rating, 35 reviews

Sleeps 9 + 3bath + 3 POOLS + boat ramp 1 mile away

•Cumberland Hilltop Hideaway located in the gated cabin community of Lake Cumberland Resort •Boat ramp 1 mile away •3 resort pools •Fire Pit •Roasting sticks for smores •Deck with dining area + 2 porches •Basement with card table & games •Indoor fireplace •Laundry & dishwasher detergent, coffee & filters •Burnside Marina 15min away with boat & slip rentals •Daniel Boone National Forest offers hiking, biking, off road vehicle riding & horseback riding •Local ATV trails