We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Vacation 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

Top guest favorite

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

5 out of 5 average rating, 11 reviews

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

Condo in Bronston

4.85 out of 5 average rating, 34 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

Cabin in Burnside

4.81 out of 5 average rating, 90 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.

Home in Burnside

4.84 out of 5 average rating, 108 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.

A rustic stone fireplace stands as a focal point in the room, featuring a wooden mantel above the fire. Warm flames flicker inside the glass enclosure, while a textured area rug lies on the wooden floor, complemented by a plaid armchair nearby.

Cabin in Burnside

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.

A charming white bungalow is framed by a well-maintained lawn and colorful flower beds. A red roof adds a pop of color, and the welcoming entrance features a brick pathway leading to the front door. American flags adorn the porch, enhancing the inviting exterior.

Home in Somerset

4.82 out of 5 average rating, 22 reviews

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.

The cabin features a welcoming facade with natural wood siding, a covered front porch adorned with hanging plants, and steps leading to the entrance. Surrounding greenery provides a serene backdrop, complementing the natural surroundings.

Cabin in Burnside

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.

Townhouse in Burnside

4.94 out of 5 average rating, 71 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.

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.

Cabin in Burnside

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.

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.

Cabin in Burnside

4.9 out of 5 average rating, 230 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!.

A charming cottage exterior is framed by lush greenery, featuring a welcoming red door with shutters. An American flag is displayed at the entrance, with a gravel path leading to the porch, which has wooden railings and a small seating area overlooking the natural surroundings.

Cabin in Burnside

4.89 out of 5 average rating, 65 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! ☆

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

4.76 out of 5 average rating, 21 reviews

The Easy Peasy/Boat Ramp/Pool/Hot Tub/Speak Easy

•Vintage 40's farmhouse w/fabulous private pool + 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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Lake Cumberland rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A vibrant sunset casts a warm orange glow over the water, reflecting shimmering colors across the surface. Silhouetted trees frame the scene, while the distant shoreline creates a serene backdrop, highlighting the natural beauty of the lake view.

Home in Somerset

Pitman Pointe w/ Lake View

The exterior of the cottage displays a covered porch with comfortable seating for relaxation. A propane grill is situated nearby on a concrete patio, surrounded by landscaping featuring black stones. The cottage is framed by green grass and a clear blue sky, enhancing the outdoor space.

Home in Somerset

5 out of 5 average rating, 4 reviews

White Oak Cottage - Resort Pool, Boat Slip

The cabin features a two-story wooden structure nestled among tall trees. A large porch with multiple columns spans the front, providing a welcoming entrance. A clear blue sky enhances the serene woodland setting, while a gentle slope leads up to the building.

Home in Burnside

4.89 out of 5 average rating, 9 reviews

Ellie's Place-Cleaning fee waived-Limited Offer!

Top guest favorite

An aerial view captures the clubhouse area featuring a large swimming pool surrounded by sunbathers. Nearby, two tennis courts and playground equipment are visible, along with a grassy area bordered by trees. Several parked cars and walkways suggest access to various amenities.

Home in Pulaski County

5 out of 5 average rating, 19 reviews

Lake-Front Woodson Bend 14-1

A seasonal pool surrounded by a spacious wooden deck is visible. Colorful float accessories, including a pizza slice and a life preserver with patriotic designs, are gently placed in the water. Comfortable seating areas are arranged on the deck, providing a relaxed outdoor setting.

Home in Burnside

4.55 out of 5 average rating, 103 reviews

Lakeside Retreat/ Jacuzzi and Private Pool

A well-lit swimming pool is surrounded by lounge chairs on a concrete deck. The pool's water glows in a vibrant blue hue under the night sky, while several green umbrellas add a touch of color. The area features a secure fence and trees in the background.

Home in Burnside

4.67 out of 5 average rating, 9 reviews

Blue Lagoon at VillagerResort,Pool,Boat slip/dock

The exterior of the home is presented, showcasing a ranch-style structure with a gabled roof. A covered porch is visible, adorned with seating. Lush greenery and colorful flowerbeds enhance the surrounding landscape, while clear blue skies provide a bright backdrop.

Home in Liberty

4.93 out of 5 average rating, 15 reviews

Teddy Hill Homestead

An outdoor entrance features a set of stairs leading to a porch area with two chairs and a decorative sign. The space is surrounded by a gravel landscape, and a nearby pathway provides access to the entrance of the unit.

Home in Pulaski County

4.86 out of 5 average rating, 7 reviews

The Bass Shack

Condo rentals with a pool

The family room features two comfortable sofas and a coffee table, with large windows allowing natural light to fill the space. The dining area, visible through an open layout, contains a wooden table with chairs, adjacent to a well-equipped kitchen.

Condo in Bronston

4.88 out of 5 average rating, 8 reviews

Woodson Bend Gorgeous Lake View Condo First Floor

Top guest favorite

A large swimming pool is surrounded by numerous lounge chairs and umbrellas, with colorful towels draped over some seats. Guests can be seen socializing near the poolside, while the building's deck features additional seating and shaded areas.

Condo in Bronston

4.98 out of 5 average rating, 49 reviews

Relaxing Cumberland Getaway

An inviting outdoor pool area is presented, surrounded by lounge chairs and umbrellas. Guests can be seen enjoying the water and the sun. Lush greenery frames the scene, enhancing the relaxing atmosphere of the resort.

Condo in Bronston

5 out of 5 average rating, 20 reviews

WoodsonBendResort 7-3 Condo 1 Brd Lake Cumberland

The exterior of the condo features a brown hue with a two-level design. A covered balcony is accessible via stairs, and a small seating area is visible on the porch. Multiple large windows provide natural light, while shrubs line the front entry.

Condo in Bronston

4.9 out of 5 average rating, 86 reviews

Gated Golf Course Condo w/view of Lake Cumberland

A spacious living area is furnished with a large sectional sofa and two stylish armchairs. A round dining table with black chairs is positioned nearby. Warm lighting is provided by lamps, and natural light filters in through two large windows, highlighting the soft beige and neutral tones of the decor.

Condo in Bronston

4.7 out of 5 average rating, 10 reviews

Amen Corner at Woodson (46-3) Golf Pool Pickleball

A spacious living area features a large sectional sofa adorned with colorful cushions, complemented by an oversized bean bag. Natural light brightens the room through sliding glass doors that lead to an outdoor space, with an open-flow view of a well-equipped kitchen.

Condo in Bronston

4.75 out of 5 average rating, 20 reviews

Lake Cumberland Resort Condo w/ Direct Lake Access

The outdoor pool area is framed by green trees and a cloudy sky. Loungers are arranged neatly around the pool, creating a spacious and relaxing environment. A lifeguard chair is positioned beside the pool, ensuring safety for all guests.

Condo in Bronston

4.74 out of 5 average rating, 38 reviews

Lakefront Condo at Woodson Bend Resort

A spacious living area is highlighted by comfortable seating, including two dark leather sofas and an armchair. Soft lighting is provided by two lamps on side tables. Framed artwork featuring tranquil landscapes is displayed on the wall, creating a welcoming ambiance.

Condo in Bronston

5 out of 5 average rating, 3 reviews

A Glimpse of the Lake (77-3) Golf Pool Pickleball

Other vacation rentals with a pool

A large private pool is surrounded by a spacious patio, featuring several lounge chairs arranged for relaxation. The pool's clear waters reflect the blue sky, while a well-maintained house and green hills are visible in the background.

Home in Wayne County

4.76 out of 5 average rating, 17 reviews

Private pool, 8 person Hot tub 6 Bedrooms

Home in Burnside

4.79 out of 5 average rating, 75 reviews

Majestic View (6E) View, Fun, Lake, Pool

A spacious living area features two dark leather sofas and a central ottoman on a decorative area rug. Natural light enters through large windows, illuminating the open layout that connects to the kitchen area, visible in the background.

Cabin in Burnside

4.87 out of 5 average rating, 78 reviews

The Gathering Place (514C) Secluded, pool, lake

Cabin in Burnside

4.78 out of 5 average rating, 9 reviews

The Love Shack (42C) Pool, Lake

Vacation home in Burnside

4.64 out of 5 average rating, 11 reviews

Lakeview Paradise (1R) Fun, Lake, Golf carts, Pool

A spacious living area is highlighted by a high vaulted ceiling and a striking spiral staircase. Light-colored furnishings and neutral walls create an open atmosphere, while natural light floods through large windows, showcasing a cozy seating arrangement and a central coffee table.

Home in Burnside

4.89 out of 5 average rating, 56 reviews

Hillside Haven (108E) Fun, Lake, Golf carts, Pool

A heated swimming pool is surrounded by lounge chairs and umbrellas, with a diving board extending over the water. The pool's clear blue water reflects the bright sky, while a building is visible in the background, providing access to additional amenities.

Home in Russell County

4.82 out of 5 average rating, 17 reviews

Lake Cumberland Ky State Park Q6

Apartment in Bronston

5 out of 5 average rating, 4 reviews

Number Two Fairway (38-4) - Golf, Pool, Pickleball

Destinations to explore