Holiday rentals with a pool in McCreary County

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

4.84 out of 5 average rating, 107 reviews

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.

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.

4.84 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.

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.

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!

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! ☆

4.89 out of 5 average rating, 82 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.

4.86 out of 5 average rating, 49 reviews

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.

4.83 out of 5 average rating, 29 reviews

Sleeps 9 + 3bath + 3 POOLS + boat ramp 1 mile away

•Cumberland Hilltop Hideaway located in the gated cabin community of Lake Cumberland Resort •Boat ramp 1 mile away •3 resort pools •Fire Pit •Roasting sticks for smores •Deck with dining area + 2 porches •Basement with card table & games •Indoor fireplace •Laundry & dishwasher detergent, coffee & filters •Burnside Marina 15min away with boat & slip rentals •Daniel Boone National Forest offers hiking, biking, off road vehicle riding & horseback riding •Local ATV trails

4.86 out of 5 average rating, 100 reviews

Home in Burnside

Cozy Cumberland Lakeview Shangri-la

A fun, lake view lake house situated on the banks of the Big South Fork River. You will love waking up each morning with a beautiful view of the river. Watch as the boats go out for a day on the water. Every where you turn, you are surround with beauty. We back up to the Daniel Boon National Forest. No matter the time of year you decide to stay, there is always plenty of hiking, fishing and site seeing to do. We are also right across the street from the pool.

Top guest favourite

Flat 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!

Holiday rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Houses

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Hotels

Stylish accommodation and amenities

Popular amenities for McCreary County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 97 reviews

Home in Caryville

Nice home close to the trails and the lake.

SydneRating, 5 stars4 weeks ago

Beautiful home and surrounding area! Great place to stay and very close to Windrock arc park!

5 out of 5 average rating, 4 reviews

Laid Back Living at Norris Lake

JulieRating, 5 stars3 days ago

House was great and they were very responsive. The golf cart was nice to get to and from the lake. My kids loved the slide and jumping off the dock. The beds were very comfortable and clean. The dock is shaded which my husband loved.

4.95 out of 5 average rating, 37 reviews

9Bed/9Bath Private Dock Quiet Cove Near Marinas

StanaRating, 5 stars1 month ago

Mary Beth's place was perfect for us and our group. It fit the entire grooms side of the wedding party as well as some family. There was plenty of bathrooms to go with all the bedrooms. Lots of fun things to do in and outside. The home is located in a quite cove of Norris lake and the views are stunning. Kitchen was very well stocked for the meals we made at home. We loved it and are planning to come back in the summer.

4.94 out of 5 average rating, 84 reviews

Lakefront Cabin-9 Bed/9 Bath-Southern Comfort II

HaleyRating, 5 stars1 month ago

We had a wonderful stay! The home was clean, comfortable and a perfect size to host our large family. Wish we could’ve stayed longer! Highly recommend!

5 out of 5 average rating, 9 reviews

Home in Monticello

Cumberland Belle Lakehouse 9bedroom,20bed,7bath

RomanRating, 5 stars2 months ago

Had a large family reunion and this location served its purpose well! The 1st floor allowed everyone ample space to be together which was fantastic. The host was great at getting back to us with questions! With all the kids there they did get a bit too adventurous and explored the woods which was someone else’s property. The host was kind(and very polite) about letting us know not to trek too far!

4.93 out of 5 average rating, 27 reviews

Chasing Wake: sleeps 24, hot tub, lakeview, dock

KaylaRating, 5 stars4 weeks ago

We had a blast at Britney’s place. She was responsive, willing to make us feel right and home and an overall great host! They were extremely flexible with our check in time and for that we were so grateful. Many memories were made here and I would absolutely book with them again! Thank you!

5 out of 5 average rating, 6 reviews

Brand New! Deerfield house w/covered boat slip!

DianaRating, 5 stars10 months ago

Beautiful condo! It was great for our family of 6. We rented a golf cart, which made it easier to get around. Chris was very responsive! We would definitely stay again!

4.73 out of 5 average rating, 15 reviews

Home in Somerset

Take It Easy@The Easy Peasy

HadenRating, 5 stars1 week ago

Misty had a great house available for us, and was great communicating through the entire process with me. Very clean, lots of room. 10/10 would recommend her as a host!

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Apartment rentals with a pool

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.

5 out of 5 average rating, 7 reviews

Apartment in LaFollette

one bedroom condo with a view

EllenRating, 5 stars3 weeks ago

This was a lovely quick getaway overlooking the lake It was wonderful to sit out on the patio.

Top guest favourite

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!

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.

4.91 out of 5 average rating, 75 reviews

Apartment in LaFollette

HappyDaze Condo: Views, Private Hot Tub, Pool, Etc

ClaudeRating, 5 stars1 month ago

Extremely clean and had everything you could possibly need to make your stay enjoyable. Great view of mountains and lake. Highly recommend!!!

4.75 out of 5 average rating, 20 reviews

Lake Cumberland Resort Condo w/ Direct Lake Access

Jeff Rating, 5 stars12 months ago

Wendy was a great host. We frequent Woodson bend and I will be saving her place as an option in the future. Walk to the pool in less than 5 minutes. The beds were comfortable. Kitchen is fully stocked with everything. You will need to purchase ice as the fridge did not make any, not a big deal since you can get a bag at the guard shack for a few bucks. The only thing I will mention is that I believe owner has a dog so if you have allergies, be mindful of this. My wife dealt with allergies during our stay so she avoided the living room and took Benadryl to help. We were gone most of the day at the pool or on the lake. Overall, nice and peaceful, would recommend.