Vacation rentals with a pool in Lake Cumberland

4.95 out of 5 average rating, 21 reviews

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

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!

A rustic kitchen and dining area features a stone fireplace, round-light pendant fixtures, and a wooden dining table with log benches. A fully equipped kitchen is visible, showing stainless steel appliances and hanging cookware. Natural light pours in through windows, enhancing the inviting space.

4.82 out of 5 average rating, 94 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.

4.84 out of 5 average rating, 110 reviews

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

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.

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.

4.9 out of 5 average rating, 10 reviews

Home in Pulaski County

The Bass Shack

Beautiful Golf & Lake retreat located on the 7th hole within Woodson Bend Resort. This is a gated community with 24 hr security, located on a 455 acre peninsula, surrounded by scenic Lake Cumberland. Amenities include a clubhouse with swimming pool (seasonal), tennis, pickleball, and basketball courts. 18 Hole golf course, 3 mile walking trail, playground, restaurant (seasonal), & boat launch. This condo is newly renovated and includes 2 bedrooms, 1 full bath, fully equipped kitchen & laundry.

Top guest favorite

A spacious living area is furnished with comfortable leather sofas and a wooden coffee table. Natural light is invited in through large windows, revealing views of the outdoors. The open layout leads to a well-equipped kitchen, with decorative stone accents on the walls.

Home in Pulaski County

5 out of 5 average rating, 19 reviews

Lake-Front Woodson Bend 14-1

1st Floor condo sits on a gorgeous Lake Cumberland. 3-5 minutes walk to the clubhouse, which features a restaurant, swimming pool, kiddie pool, 6 dedicated Pickleball Courts, 2 tennis courts, basketball, volleyball, and playground. Well-appointed kitchen with stainless appliances features a bar area perfect for entertaining! The screened-in heated and cooled back porch w/lake views and a gas grill. The Primary bedroom has a king-size bed and Bedroom 2-Queen and Bedroom 3-Queen w/twin trundle.

4.83 out of 5 average rating, 23 reviews

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

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.

4.75 out of 5 average rating, 24 reviews

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

Lakefront Sunsetter at The Villager

This lakefront estate is perfect for your large family/friends gatherings! It offers lake access steps away, with a private boat slip and a fishing dock. The house has a full basement of gaming fun for all ages to enjoy (pool table, air hockey, and shuffleboard). Comfortably sleeps up to 26 guests, with KING beds in 7 of 8 bedrooms. Just across the driveway is our shared swimming pool, arcade area, and a tennis court. When you get off the lake, relax in the Hot Tub overlooking the lake.

4.94 out of 5 average rating, 72 reviews

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

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 favorite

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.

4.93 out of 5 average rating, 72 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 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.

4.9 out of 5 average rating, 234 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.