Holiday 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 favourite

A modern kitchen is displayed with sleek cabinetry and stainless steel appliances. A large wooden island is accompanied by four high-backed black stools. Lighting fixtures with intricate designs hang above, adding a stylish touch to the functional space.

Home in Monticello

4.92 out of 5 average rating, 12 reviews

Cumberland Belle Lakehouse 9bedroom,20bed,7bath

Lake Cumberland - 9 bedrooms 7 baths, 20 beds. Great for big groups. New SwimSpa (large hot tub/small lap pool) & sauna! 1/2 mile from Beaver Creek Marina. 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 favourite

The kitchen space features white cabinetry paired with sleek black appliances. A central island with bar seating provides a casual dining option. Natural light enters through the nearby window, illuminating the wooden countertop and hardwood flooring.

Apartment 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

Guest favourite

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

4.96 out of 5 average rating, 23 reviews

Teddy Hill Homestead

Teddy Hill Homestead is 2 miles from many Amish stores and markets. 6 miles from the Bread of Life. 16 miles from Lake Cumberland. 33 miles from Wolf Creek Dam. 5 minutes from the Green River with several spots to enter with kayaks. Lots of opportunities to see the rolling hills and soothing waterways of Kentucky. A little over 1,800 square feet with 2 bedrooms, large open living/dining/kitchen, large bathroom with walk in shower, half bath with laundry, game room, closet space, and a POOL!

Superhost

A panoramic view showcases lush greenery surrounding a winding river. The landscape is dotted with trees under a clear blue sky, and distant hills create a serene backdrop. The natural light enhances the beauty of the scene, providing a tranquil atmosphere.

Home in Burnside

4.84 out of 5 average rating, 112 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.

Guest favourite

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

4.9 out of 5 average rating, 21 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.

Guest favourite

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, 24 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.

Guest favourite

A serene outdoor scene features several tall trees with autumn foliage in shades of orange and yellow. The grassy area nestled between the trees leads to a glimpse of a calm lake, enhancing the natural beauty of the lakeside setting.

Townhouse in Burnside

4.93 out of 5 average rating, 74 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.

Top guest favourite

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, 73 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.

Guest favourite

The exterior of the cabin features a wooden facade with dark green accents. A spacious screened-in porch is accessible via a set of steps. Rocking chairs are arranged on the porch, and colorful flower beds line the base of the structure, complemented by landscaping stones.

Cabin in Burnside

4.89 out of 5 average rating, 242 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 favourite

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

4.88 out of 5 average rating, 77 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 favourite

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.

Apartment in Bronston

4.89 out of 5 average rating, 88 reviews

Gated Golf Course Condo w/view of Lake Cumberland

Our condo is located on a 400 acre peninsula surrounded by Lake Cumberland. Gated community with 18 hole golf course, swimming pool, sand volleyball, full outside basketball court, tennis courts, pickle ball courts, workout room, library, restaurant, 3 mile road track for those who like to run or walk with a view of Lake Cumberland. Condo has Wifi and Roku tv's. Our condo is located straight across from the pool with a view of Lake Cumberland within a short walking distance.

Top guest favourite

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, 9 reviews

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

•Classic home w/fabulous private pool (seasonal) •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