Holiday rentals with a pool in Somerset

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.

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

4.95 out of 5 average rating, 22 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 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.

4.84 out of 5 average rating, 111 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.

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.

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.

5 out of 5 average rating, 19 reviews

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

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.

4.93 out of 5 average rating, 14 reviews

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

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.

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.

4.75 out of 5 average rating, 24 reviews

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.

4.95 out of 5 average rating, 73 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.

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, 236 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.

4.89 out of 5 average rating, 72 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! ☆

Popular amenities for Somerset rentals with a pool

Kitchen

Wi-Fi

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.

Pitman Pointe w/ Lake View

5 out of 5 average rating, 11 reviews

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

Cumberland Belle Lakehouse-5bedrm,10bed,5bath

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.

5 out of 5 average rating, 5 reviews

White Oak Cottage - Resort Pool, Boat Slip

4.89 out of 5 average rating, 9 reviews

Ellie's Place-Your Autumn Getaway!

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.

4.68 out of 5 average rating, 25 reviews

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

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.

4.83 out of 5 average rating, 23 reviews

Burnside Bungalow, w/ dock, pool & firepit

4.68 out of 5 average rating, 19 reviews

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

Lake Cumberland Ky State Park Q6

An aerial view showcases a lakeside home surrounded by trees, with a pool and large deck visible in the backyard. The tranquil waters of Lake Cumberland reflect the landscape, highlighting the serene setting. Ample parking can be seen along the private driveway.

4.55 out of 5 average rating, 107 reviews

Lakeside Retreat/ Jacuzzi and Private Pool

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.

4.88 out of 5 average rating, 8 reviews

Woodson Bend Gorgeous Lake View Condo First Floor

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, 49 reviews

Relaxing Cumberland Getaway

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

A spacious living area features a comfortable dark sofa with decorative pillows, a light table with a lamp, and a patterned chair. Large windows allow natural light, while a door leads to an outdoor space. A textured rug enhances the inviting atmosphere.

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.

4.75 out of 5 average rating, 20 reviews

Lake Cumberland Resort Condo w/ Direct Lake Access

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.

4.75 out of 5 average rating, 40 reviews

Lakefront Condo and 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.

5 out of 5 average rating, 3 reviews

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

The living area features a floral-patterned sofa, paired with two armchairs, providing comfortable seating. A light-colored coffee table sits at the center, while two table lamps illuminate the space. Large windows allow natural light to enhance the serene atmosphere.

Bigelow's Water View Bungalow (93-3) Golf, Pool

Other holiday rentals with a pool

The exterior of a large two-story home is presented, featuring a green metal roof, a welcoming porch, and a grassy yard. Surrounding trees provide a natural backdrop, while steps lead up to the first floor entrance. Various outdoor spaces are visible for relaxation.

Home in Monticello

Cumberland Belle Lakehouse 4bedrm, 10bed, 2.5bath

4.78 out of 5 average rating, 9 reviews

A single-story blue house is set amidst tall trees under a clear blue sky. A concrete pathway leads up to the entrance, and a well-maintained green lawn surrounds the home.

Cottage in Burnside

Studio 34 at Villager, Pool,Boat slip/dock

A bright living area features a modern gray sectional sofa, a patterned chair, and a glass coffee table. Natural light enters through large windows adorned with soft curtains. A propane fireplace adds warmth, while the open layout leads to the kitchen visible in the background.

4.78 out of 5 average rating, 9 reviews

The Love Shack (42C) Pool, Lake

A comfortable living area is presented, featuring a gray sofa adorned with throw pillows. A round wooden table occupies the center, topped with decorative items, including a lamp and a small book. Light filters through sheer curtains, highlighting the patterned area rug.

4.9 out of 5 average rating, 10 reviews

Kellerman’s at VillagerResort-Pool, Boat slip/dock

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.

4.89 out of 5 average rating, 57 reviews

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

4.83 out of 5 average rating, 29 reviews

The studio suite features a spacious bed with a textured blanket, complemented by rustic barn wood accents. A dining area with a wooden table and four chairs is visible, along with a fully equipped kitchen. Large windows brighten the space, framed by simple blinds.

Apartment in Burnside

The Rustic Suite (500A)Fun, Lake, Golf carts, Food

4.8 out of 5 average rating, 5 reviews

A single-story building with a red exterior and a metal roof is situated beside a well-maintained grassy area. Large windows allow natural light to enter, and a welcoming porch leads to the entrance. Nearby, additional buildings can be seen in a contrasting blue hue.

Cottage in Burnside

Marley at Villager Resort-Pool,Boat slip/dock

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.