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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.

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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

Home in Burnside

4.83 out of 5 average rating, 109 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.

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 cozy living area features a spacious gray sectional sofa adorned with decorative cushions. Light-colored wooden coffee tables are positioned on a patterned rug. Natural light filters through bamboo shades on multiple windows, creating a relaxed ambiance. A flat-screen TV is mounted on the wall.

Cottage in Burnside

4.93 out of 5 average rating, 14 reviews

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.

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.

Top guest favorite

Cabin in Burnside

4.93 out of 5 average rating, 71 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, 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!

Cabin in Burnside

4.88 out of 5 average rating, 68 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 crystal-clear community swimming pool is showcased, with inviting blue water reflecting the surroundings. The pool area includes a set of stairs leading into the water and loungers positioned along the edge for relaxation.

Townhouse in Burnside

4.87 out of 5 average rating, 53 reviews

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.

The exterior of a rustic cabin is featured, showcasing a wooden ramp leading to the entrance. Surrounding greenery includes several trees and flower beds. A small American flag adorns the front porch, adding a welcoming touch to the natural setting.

Cabin in Burnside

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

A spacious patio area features a large smoker and gas grill. In the background, an in-ground pool is visible, complete with a slide and surrounded by a secure fence. Lush trees provide shade, and the sky is clear with a hint of blue.

Home in Somerset

5 out of 5 average rating, 4 reviews

Cumberland Classic/Boat Ramp/Private Pool/Bar/City

•Classic home w/fabulous private pool •Centrally-located, 2 min. to boat ramp + 7 to marina •Man Cave themed basement w/full bar •Equipped kitchen + dedicated dining room •3 BR, 3 full baths w/vintage decor + modern amenities •Outdoor dining + fire pit •Pool essentials + towels stocked •Private office w/desk + printer •Multiple sitting/game/reading areas •Full, on-site laundry •Huge yard for outdoor play •Close to shopping + dining •Boat/trailer parking

Vacation rentals for every style

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Houses

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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

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

A spacious lakefront estate is shown, featuring a drive-up area and a well-maintained lawn. The house has multiple gabled roofs, large windows, and a welcoming front porch adorned with seating. A two-car garage is visible to the right.

Home in Somerset

4.75 out of 5 average rating, 24 reviews

Lakefront Sunsetter at The Villager

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!

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

4.83 out of 5 average rating, 23 reviews

Burnside Bungalow, w/ dock, pool & firepit

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

4.54 out of 5 average rating, 105 reviews

Lakeside Retreat/ Jacuzzi and Private Pool

An outdoor pool is surrounded by a wooden deck, featuring a sturdy railing for safety. The blue water reflects the surrounding greenery and blue skies. The deck provides ample space for lounging and enjoying the views of the nearby hills.

Home in Liberty

4.95 out of 5 average rating, 20 reviews

Teddy Hill Homestead

Home in Pulaski County

4.89 out of 5 average rating, 9 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

4.89 out of 5 average rating, 88 reviews

Gated Golf Course Condo w/view of Lake Cumberland

Condo in Bronston

Green Lite Lakeview (105-1) Lake, Golf, Pool

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

4.75 out of 5 average rating, 40 reviews

Lakefront Condo at Woodson Bend Resort

Condo in Bronston

4.46 out of 5 average rating, 13 reviews

On the Green (71-4) WB - Golf, Pool, Pickleball

Other vacation rentals with a pool

Cabin in Burnside

4.68 out of 5 average rating, 31 reviews

The Retreat on the Hill (411C) Fun, Lake, Pool

Home in Burnside

4.79 out of 5 average rating, 76 reviews

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

Cabin in Pulaski County

4.92 out of 5 average rating, 12 reviews

M&M's Lake Retreat (23V) Lake, Pool, Boat ramp

Top guest favorite

Townhouse in Burnside

4.94 out of 5 average rating, 71 reviews

Lakeside Hideaway I - lakefront w/hot tub

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

Home in Burnside

4.89 out of 5 average rating, 57 reviews

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

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

4.71 out of 5 average rating, 24 reviews

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

Destinations to explore