Vacation rentals with a pool in Lake Cumberland

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Top-rated rentals with a pool in Lake Cumberland

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

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Guest favorite

Home in Monticello

5 out of 5 average rating, 7 reviews

Cumberland Belle Lakehouse 9bedroom,20bed,7bath

Lake Cumberland - New SwimSpa (large hot tub/small lap pool) & sauna! 1/2 mile from Beaver Creek Marina. 9 bedrooms 7 baths, 20 beds. Great for big groups. 2 Large decks, 1 of which is covered, 2 full kitchens, 2 living rooms and outdoor/ indoor dining for up to 30+. Lots of games (skeeball, popashot, arcade, air hockey, etc). 1st floor has no stairs. Must be comfortable with stairs for the 2nd floors. Plenty of boat/truck parking. Only 8 miles to town. View Q R Code to tour & see floor plan.

Guest favorite

Home in Jamestown

4.96 out of 5 average rating, 52 reviews

Serene Family Getaway*Lake Cumberland*Pet Friendly

Escape from the hustle and bustle, get back to nature, and revel in the peace and quiet at this beautifully remodeled cabin near Lake Cumberland. Situated on Timber Pointe Resort, guests at this home benefit from the resort's amenities, while enjoying the privacy this cabin offers. This is the perfect getaway for those who love fishing, hiking, & site-seeing. 1.1 mi: Lake Cumberland 1.3 mi: Safe Harbor Marina Timber Point Grille+Pool on resort premises Experience Lake Cumberland with us!

Guest favorite

Farm stay in Somerset

4.98 out of 5 average rating, 58 reviews

23 Acre Lake Cumberland: Boats & Fishing Oasis

Escape to a 5-star, 23-acre private lake estate, your ultimate outdoor retreat by Lake Cumberland.. Enjoy our 3-acre fishing pond with all gear provided, kayaks and boats. Relax in a luxurious 8-person hot tub, savor meals on Traeger & egg grills & 2 fire-pits. Inside, find a cozy fireplace, high-speed Wi-Fi, Smart TVs, full bath and half bath plus a gourmet kitchen. Experience Lake Cumberland with our rentals, and let me be your guide to the best hidden gems. Your dream vacation awaits!

Guest favorite

Cabin in Burnside

4.85 out of 5 average rating, 33 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 favorite

Townhouse in Burnside

4.92 out of 5 average rating, 53 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 favorite

Cabin in Burnside

4.91 out of 5 average rating, 58 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

4.91 out of 5 average rating, 204 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 favorite

Cabin in Burnside

4.91 out of 5 average rating, 35 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! ☆

Guest favorite

Home in Somerset

5 out of 5 average rating, 69 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 favorite

Cabin in Burnside

5 out of 5 average rating, 36 reviews

Lakin' It Easy | Lake House | Hot Tub | Boat Ramp

Welcome to your ultimate getaway at Lakin' It Easy near the picturesque Lake Cumberland! Inside, our three secluded bedrooms offer a haven of comfort and privacy, ensuring a restful night's sleep after a day of exploration. Whether you're seeking a romantic retreat, a family getaway, or a solo escape, Lakin' It Easy has something for everyone. ☆Book your stay at Lakin' It Easy today and discover why life truly is better by the lake. Your perfect retreat awaits!☆

Guest favorite

Home in Burnside

4.9 out of 5 average rating, 89 reviews

Cozy Cumberland Lakeview Shangri-la

A fun, lake view lake house situated on the banks of the Big South Fork River. You will love waking up each morning with a beautiful view of the river. Watch as the boats go out for a day on the water. Every where you turn, you are surround with beauty. We back up to the Daniel Boon National Forest. No matter the time of year you decide to stay, there is always plenty of hiking, fishing and site seeing to do. We are also right across the street from the pool.

Superhost

Cabin in Burnside

4.69 out of 5 average rating, 72 reviews

Majestic Lake Cabin | Boat Ramp | Hot Tub

Escape to this hidden gem nestled within the gated Lake Cumberland Resort community, where tranquility meets luxury. With 24/7 security, pristine blacktop roads, and meticulously manicured landscaping, your stay promises both serenity and security. Unwind with an evening stroll through the serene neighborhood, gather around the crackling campfire, or simply bask in the warmth of the sun. Your tranquil retreat awaits—book your stay today at Majestic Cabin!