Holiday rentals with a pool in Somerset

4.94 out of 5 average rating, 33 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!

FamilyLocationComfort

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, 114 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.

FamilyLocationBathroom

4.92 out of 5 average rating, 12 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.

FamilyLocationLaundry

A partially enclosed porch features a hot tub illuminated by soft lighting. Two white chairs are positioned near the hot tub, with wooden decking visible outside. Trees and natural greenery can be seen through the protective screens, creating a serene outdoor ambiance.

4.91 out of 5 average rating, 22 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.

LocationFamilySleep quality

Townhouse in Pulaski County

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.

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.

FamilyLocationHiking

4.83 out of 5 average rating, 24 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.

LocationFamilyAccess

4.78 out of 5 average rating, 60 reviews

Woodson Bend Resort Golf/Pool/Pickleball and More!

Welcome to your perfect getaway! This beautifully decorated rustic condo sits directly across from the swimming pool, on-site restaurant, and tennis/pickleball courts, all within a stunning resort community centered around an 18-hole championship golf course. Step outside and you’re just moments from the volleyball and basketball courts, plus a nearby playground—making this an ideal spot for couples, golfers, families, and adventure-seekers alike. The perfect home base for your getaway!

LocationFamilyBarbecue

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.

4.94 out of 5 average rating, 83 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.

FamilyLocationOutdoor spaces

4.89 out of 5 average rating, 272 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!

LocationValuePool

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.

4.9 out of 5 average rating, 101 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! ☆

FamilyValuePets

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.

4.89 out of 5 average rating, 91 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.

FamilyLocationIndoor spaces

4.87 out of 5 average rating, 54 reviews

A serene lakeside view is framed by tall trees and natural vegetation. The calm water reflects the greenery, creating a peaceful atmosphere. Large rocks and foliage are visible in the foreground, leading towards the water's edge.

Townhouse in Burnside

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.

ValueFamilyOutdoor spaces

Popular amenities for Somerset rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Bronston

Woodson Bend Resort Seven-Tee's

Hospitality

Home in Burnside

New place to stay

Casa Marina

Home in Burnside

4.92 out of 5 average rating, 12 reviews

Ellie's Place- "Wow, this is nice!" Woodsy Getaway

FamilyLocationCheck-in

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

4.7 out of 5 average rating, 27 reviews

Lakefront Sunsetter at The Villager

LocationFamilyPool

Superhost

Home in Bronston

Woodson Bend - Golf Cart included- 22 Fairway View

Family

Home in Jamestown

Lake Cumberland Resort Retreat

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

4.53 out of 5 average rating, 15 reviews

Cumberland Classic/near Boat Ramp/Private Pool

FamilyLocationAmenities

Home in Jamestown

New place to stay

The Lodge @ Lake Cumberland

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.

4.89 out of 5 average rating, 9 reviews

Woodson Bend Gorgeous Lake View Condo First Floor

LocationFamilyAccuracy

The exterior of a two-story wood-paneled condo is depicted, adorned with colorful patriotic decorations. A large American flag hangs from the porch, and several plants are visible nearby. Ample windows allow natural light, while a grassy area surrounds the entrance.

5 out of 5 average rating, 20 reviews

WoodsonBendResort 7-3 Condo 1 Brd Lake Cumberland

FamilyLocationCleanliness

A two-story condo structure is surrounded by greenery, featuring a tree in the foreground and well-maintained grass. The building displays a mix of large windows and balconies, allowing for natural light to enter. A stone border outlines the walkway leading up to the entrance.

4.98 out of 5 average rating, 50 reviews

Relaxing Cumberland Getaway

FamilyLocationSleep quality

4.25 out of 5 average rating, 4 reviews

Seventh Heaven (21-3) - Golf, Pool, Pickleball

FamilyLocationCondition

New place to stay

Lakeview Treehouse (18-2)- Golf, Pool, Pickleball

LocationViewAccuracy

The entrance sign for Woodson Bend Resort is framed by natural stone and surrounded by well-maintained landscaping. Tall trees stand in the background, creating a serene setting that invites guests into the resort.

4.76 out of 5 average rating, 42 reviews

Lakefront Condo at Woodson Bend Resort

FamilyLocationCheck-in

4.85 out of 5 average rating, 34 reviews

Lovely 4-bedroom lake condo with golf and a pool

LocationValueNearby

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.

5 out of 5 average rating, 5 reviews

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

LocationCleanlinessIndoor spaces

Other holiday rentals with a pool

5 out of 5 average rating, 5 reviews

Lake Cumberland Resort | Hot Tub, Pools & Forest

LocationFamilyQuiet

5 out of 5 average rating, 8 reviews

The cottage features a large covered deck, with outdoor seating arranged around a picnic table. A grassy area surrounds the structure, which has a metal roof and green siding. A charcoal grill is visible nearby, with trees providing a natural backdrop.

Cottage in Somerset

SunnyDaze Cottage Lake Cumberland Resort boat dock

LocationFamilyNearby

4.89 out of 5 average rating, 130 reviews

Cozy Hillside Cabin

FamilyValueQuiet

An indoor pool area features an elongated pool with clear water, surrounded by light-colored walls and several lounge chairs. A handrail provides access to the water, while large windows allow natural light to fill the space.

Apartment in Russell Springs

4.5 out of 5 average rating, 12 reviews

Resort Clubhouse

ValueFamilyKitchen

4.92 out of 5 average rating, 13 reviews

The entrance of Woodson Bend Resort is marked by a stone sign set within a landscaped garden. Lush green plants surround the sign, creating a welcoming view among the trees that provide a natural backdrop.

Apartment in Bronston

Woodson Bend Resort getaway on Lake Cumberland.

LocationFamilyNearby

4.8 out of 5 average rating, 50 reviews

Burnside Resort Cabin w/ Hot Tub & Outdoor Spots!

FamilyLocationWalkability

5 out of 5 average rating, 10 reviews

A modern cabin is presented in a deep blue hue, featuring clean lines and a welcoming front porch. Outdoor seating is arranged with several chairs, inviting relaxation. A wooden railing adds safety and charm, while a small American flag decorates the side of the cabin.

Cabin in Somerset

Cozy Cabin at Villagers Resort, Lake Cumberland KY

LocationFamilyHospitality

A rustic cabin constructed with natural wood materials sits among lush greenery. The structure features a peaked roof and multiple windows, while a wooden deck extends from its side, offering a view of the surrounding forested area. A stone pathway leads to the entrance.