Vacation rentals with a pool in Lake Cumberland

5 out of 5 average rating, 5 reviews

The two-story building features a welcoming yellow entrance and expansive covered decks on both levels. A gravel driveway leads up to the property, with trees lining the background and a soft sunset sky providing a warm backdrop.

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

4.86 out of 5 average rating, 29 reviews

Condo in Bronston

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

4.84 out of 5 average rating, 105 reviews

Home in Burnside

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.

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.

4.63 out of 5 average rating, 8 reviews

A circular fire pit area is surrounded by five red Adirondack chairs set atop gravel. The sunny outdoor space features a neatly arranged stone perimeter, with a grassy area beyond, creating an inviting atmosphere for gatherings.

Home in Somerset

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

A community pool is surrounded by a concrete deck, featuring several lounge chairs positioned neatly along the edge. Lush greenery and trees are visible in the background, enhancing the serene atmosphere. The pool's clear blue water reflects the daylight, inviting relaxation.

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.

4.94 out of 5 average rating, 64 reviews

Townhouse in Burnside

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.

A spacious cabin exterior is displayed, featuring a welcoming porch surrounded by tall, neatly trimmed conifer trees. The screened lower deck showcases several red lounge chairs, providing a relaxing outdoor area. The lush green lawn complements the natural surroundings, enhancing the inviting outdoor space.

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.

The swimming pool is surrounded by a paved patio and enclosed by a fence. Bright blue water reflects the sky, and there are several lounge chairs positioned nearby for relaxation. Trees provide natural shade in the background, enhancing the tranquil setting.

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!

An outdoor pool area is surrounded by lush trees, offering a serene environment. Sun loungers are arranged neatly around the water, where sunlight reflects on the clear blue surface. A small pool house is visible, providing amenities and shade.

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 favorite

An aerial view captures the expansive outdoor space, featuring a circular above-ground pool surrounded by a fenced area. A patio with seating arrangements is visible, alongside green grass and landscaping elements. The backdrop consists of lush trees, enhancing the natural setting.

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!

The exterior of a two-story home is shown, featuring a wrap-around porch with wooden railings. Autumn foliage surrounds the house, showcasing vibrant orange and yellow leaves. Windows line the front, providing ample natural light, and a well-maintained lawn leads up to the structure.