Vacation rentals with a pool in Lake Cumberland

4.86 out of 5 average rating, 29 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

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.

4.75 out of 5 average rating, 8 reviews

Blue Lagoon at VillagerResort,Pool,Boat slip/dock

Have fun with the whole family at this stylish place. Blue Lagoon 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 swimming pool is surrounded by multiple lounge chairs and an umbrella-protected table. Lush trees provide a green backdrop, enhancing the outdoor setting. Two individuals are seen swimming in the clear blue water, while others are gathered nearby, engaged in conversation.

4.84 out of 5 average rating, 107 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.

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.

4.89 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.

4.73 out of 5 average rating, 15 reviews

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

Take It Easy@The Easy Peasy

•Vintage 40's farmhouse w/fabulous private pool (closed for season)+ hot tub area •Centrally-located, 2 min. to boat ramp+ 7 to marina • Hidden speak-easy themed basement bar w/pool + poker tables, shuffle board,+ more (search home for entrance+code) •Equipped country kitchen+sunroom w/drink fridge, games,+ coffee bar. •Unique attic space for family fun (lake house+camp themed w/games+movies) • 5 BR, 2 full baths-1st retro styled w/soaking tub, 2nd w/double sink+walk-in shower • Pet friendly

4.79 out of 5 average rating, 19 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.

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.

4.84 out of 5 average rating, 38 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.

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, 67 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.

4.91 out of 5 average rating, 222 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.

4.88 out of 5 average rating, 57 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! ☆

4.86 out of 5 average rating, 49 reviews

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

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.

Top guest favorite

An open living space features a cozy fireplace and an entertainment center with a large screen. The kitchen island with seating is surrounded by light-colored cabinetry. Natural light fills the room, highlighting the smooth wooden flooring.

Apartment in Bronston

5 out of 5 average rating, 12 reviews

Cumberland Condo WB 36-3

Relaxing three-bedroom, two-bath condo at the beautiful Woodson Bend Resort on Lake Cumberland! This property boasts 24-hour security, golf, hiking, swimming, exercise room, basketball, volleyball, pickleball, tennis, a driving range, and magnificent views of Lake Cumberland. Get ready to relax and enjoy everything nature has to offer. Frequent deer sightings along the fairways right outside this condo makes for many serene mornings and evenings!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Lake Cumberland rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 7 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

AdemRating, 5 stars2 weeks ago

The home was very clean, unique, and had an awesome vacation vibe. The hosts were very quick to answer questions and very accommodating. I would definitely recommend the home and plan on coming again!

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

White Oak Cottage - Resort Pool, Boat Slip

SageRating, 5 stars4 weeks ago

Awesome places with dock access on a beautiful lake.

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.

5 out of 5 average rating, 8 reviews

Ellie's Place-Bring Your Boat or ATV & Enjoy.

SamanthaRating, 5 stars1 week ago

Great house! We had a girls weekend here and had a blast. Loved the hot tub, close to Burnside and Conley Bottom. We really enjoyed the screened in back porch and were in the hot tub every night. Dave even let us have an early check-in! All instructions were clear! Would definitely stay here again!

A private pool is set against a lush, green backdrop, surrounded by blue adirondack chairs for relaxation. The clear water reflects the sky, while a well-maintained patio area is featured, offering scenic views of the nearby waterfront.

Home in Monticello

4.72 out of 5 average rating, 54 reviews

Private pool and hot tub overlooking the Lake !

BrianRating, 5 stars1 week ago

Beautiful scenery, great amenities and very private without being far from the main road.

Top guest favorite

Home in Pulaski County

5 out of 5 average rating, 16 reviews

Lake-Front Woodson Bend 14-1

JenniferRating, 5 stars3 months ago

We stayed at this beautiful condo while we were in town looking at real estate. WOW, what great spot on the lake. The view was fantastic. The sheets smell fantastic too! I would recommend staying here for sure. Everything you need and more. What are you waiting for, book this one today!

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.

4.57 out of 5 average rating, 94 reviews

Lakeside Retreat/ Jacuzzi and Private Pool

AmandaRating, 5 stars2 weeks ago

The pool was a hit for our son! There were lots of games and puzzles. The beds were super comfy! And there is plenty of space! The kitchen had a lot of dishes. Make sure to bring a sharp knife if you are going to do a lot of cooking. Dont forget your corkscrew if you like to enjoy a glass of wine! Over all it was really nice! We saw a snake and a box turtle out walking our dogs! It was a tiny snake don’t worry! This is a great spot for the family!

The exterior of a spacious homestead features a covered porch with seating and an American flag. The façade is complemented by a sloped roof and multiple windows. Colorful chairs are positioned around a dining area, set against a backdrop of greenery and a gravel pathway.

Home in Liberty

5 out of 5 average rating, 5 reviews

Teddy Hill Homestead

MalissaRating, 5 stars1 day ago

We had such a wonderful stay at Teddy Hill Homestead! Jeff and Angie were incredibly warm, welcoming, and attentive-truly going above and beyond to make sure our stay was pleasant. They added such a personal and genuine touch to our experience. The open-concept layout of the home was nice and made everything feel so spacious and inviting. Loved the walk in shower! We especially enjoyed the pool-it was the perfect spot to relax and cool off. Another highlight was the location! We loved exploring all the local shops nearby and just up the road is a creek that brings you much peace and relaxation. Teddy Hill Homestead is the kind of place that instantly calms your mind and helps you reconnect with nature and yourself. Highly recommend for anyone looking for a peaceful and memorable getaway!

A spacious swimming pool is surrounded by lounge chairs, offering a refreshing blue hue. A shallow entry with metal steps provides easy access to the water. The pool area is fenced, with trees and a small building visible in the background.

4.86 out of 5 average rating, 100 reviews

Cozy Cumberland Lakeview Shangri-la

Albert ARating, 5 stars3 weeks ago

Taja very responsive. Place is very clean and smells very fresh. Would recommend this place.

Show all

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.

4.83 out of 5 average rating, 6 reviews

Woodson Bend Gorgeous Lake View Condo First Floor

MegRating, 5 stars23 months ago

Woodson Bend is always a great place to be. We love the pool, ability to put your own boat in the water at the resort, the golf and the golf cart community. Debbie’s place is clean, well stocked and as it is shown in the pictures and description.

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.

4.98 out of 5 average rating, 42 reviews

Relaxing Cumberland Getaway

MarciaRating, 5 stars9 months ago

Always such a wonderful place to stay. Beth is quick to respond and makes certain every detail is covered. Such a warm and inviting home!

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.

5 out of 5 average rating, 19 reviews

WoodsonBendResort 7-3 Condo 1 Brd Lake Cumberland

StoneRating, 5 stars1 month ago

Tony provided an amazing place for me to stay for two months. It truly felt like home away from home. He was very responsive and more than helpful with any questions or requests. There are also tons of activities within a couple minute walk, the resort offers bocce ball, beach volleyball, a playground, a real putting green, a pool and more.

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, 82 reviews

Gated Golf Course Condo w/view of Lake Cumberland

ShondaRating, 5 stars8 months ago

This condo was beautifully decorated and very clean. The furniture was very comfortable. The location was great and the area was very peaceful. The owner was super friendly and easy to work with. We were a last minute booking and a late arrival and he was ver accommodating. Will definitely stay her again.

A spacious living area is furnished with a large sectional sofa and two stylish armchairs. A round dining table with black chairs is positioned nearby. Warm lighting is provided by lamps, and natural light filters in through two large windows, highlighting the soft beige and neutral tones of the decor.

4.88 out of 5 average rating, 8 reviews

Amen Corner at Woodson (46-3) Golf Pool Pickleball

BenjaminRating, 5 stars4 weeks ago

Great Location. Great place. Dianna was very responsive and trip was good.

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.

ThuyRating, 5 stars4 weeks ago

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

I had a wonderful stay! The community here is truly beautiful, with a warm and welcoming atmosphere that immediately made me feel at home. The host was fantastic—attentive, friendly, and always ready to help with anything I needed. Every detail was thoughtfully taken care of, ensuring that I had exactly what I was looking for during my visit. I couldn’t have asked for a better experience, and I would gladly stay here again in a heartbeat.

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.