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Holiday rentals with a pool in Lake Cumberland

Find and book unique homes with a pool on Airbnb

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Popular amenities for Lake Cumberland rentals with a pool

House rentals with a pool

Home in Wayne County
4.69 out of 5 average rating, 13 reviews

Private pool, 8 person Hot tub 6 Bedrooms

JanellRating, 5 stars7 months ago
This was perfect for our large group. We didn't want for anything. So many options with a view of the beautiful lake (pool and hot tub area, fire pit, large porch with the option to have windows opened or closed). Plenty of space to spread out or all gather together. No complaints here and would definitely rent again.
Guest favourite
Home in Burnside
5 out of 5 average rating, 6 reviews

Ellie's Place-Best ever '25 Rates. Book Now!

MacRating, 5 stars2 weeks ago
This place is amazing, super quiet and very private. It made for a relaxing stay after doing all the touristy things around town. The hot tub is comfortable and private, with a beautiful view of the trees. We will definitely be back!
Home in Somerset
4.71 out of 5 average rating, 21 reviews

Lakefront Sunsetter at The Villager

KorinneRating, 5 stars3 months ago
This house did not disappoint! Went for a family reunion with extended family ages 8-80! Something for everyone to enjoy. The great room was perfect for our large gathering with plenty of space for games, kids and visiting. Kitchen was perfect for our needs (some repair issues Clay is addressing did not overly affect our stay - he’s super responsive and helpful!). Table for 8 plus counter height seating for another 6 or so in the kitchen itself. Tons of bedrooms offer privacy and comfort for everyone. 2 showers on main floor, one in basement and one on 2nd floor. Basement is teenager heaven! Poor, shuffleboard, Nintendo and air hockey as well as a bar area with another refrigerator which was awesome for drinks. Hot tub outside on the porch was great. I think our favorite was the deck outside the great room had lots of seating so we could enjoy the unseasonable 60 degree weather! Never got a chance to use the fire pit looked awesome. Highly recommend - we will definitely be back!
Superhost
Home in Somerset
4.78 out of 5 average rating, 18 reviews

Burnside Bungalow, w/ dock, pool & firepit

LuisRating, 5 stars3 months ago
Place is amazing! Felt like home, once we left we started to miss it. Extremely spacious, amenities were amazing. Would recommend to anyone who wants to visit Somerset!
Top Guest favourite
Home in Pulaski County
5 out of 5 average rating, 16 reviews

Lake-Front Woodson Bend 14-1

JenniferRating, 5 stars1 month 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!
Home in Burnside
4.55 out of 5 average rating, 85 reviews

Lakeside Retreat/ Jacuzzi and Private Pool

ChristinaRating, 5 stars2 weeks ago
My family and I travelled here during spring break. The place is beautiful, felt right at home. We love Kentucky! We will definitely return during another vacation - we want to go back when the pool is open. There is so much do around Burnside, Somerset, and surrounding areas. Highly recommended if you need a quick get away from reality!

Condo rentals with a pool

Condo in Bronston
4.83 out of 5 average rating, 6 reviews

Woodson Bend Gorgeous Lake View Condo First Floor

MegRating, 5 stars21 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 favourite
Condo in Bronston
4.98 out of 5 average rating, 41 reviews

Relaxing Cumberland Getaway

JeffreyRating, 5 stars7 months ago
We've been coming to Woodsen Bend for over 30 yrs and have rent too many unit's to remember. Beth's unit is clearly the most comfortable, and well appointed we have ever rented. She has prepared a home away from home. Amazing from A to Z.
Guest favourite
Condo in Bronston
5 out of 5 average rating, 18 reviews

WoodsonBendResort 7-3 Condo 1 Brd Lake Cumberland

CraigRating, 5 stars6 months ago
Tony’s place was absolutely phenomenal. It was in great condition, we had 4 guys and each had their own spot to sleep comfortably. Absolutely no complaints and already planning a golf trip next year
Guest favourite
Condo in Bronston
4.89 out of 5 average rating, 81 reviews

Gated Golf Course Condo w/view of Lake Cumberland

ShondaRating, 5 stars6 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.
Guest favourite
Condo in Bronston
4.86 out of 5 average rating, 7 reviews

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

ChristineRating, 5 stars9 months ago
We have been going to Woodson Bend since I was a kid. We finally outgrew my parents place and needed a place of our own. We had a great stay at this Condo. We have 4 kids and the bunk beds were great, the condo was clean, and they had very detailed instructions.
Condo in Bronston
4.75 out of 5 average rating, 20 reviews

Lake Cumberland Resort Condo w/ Direct Lake Access

Jeff Rating, 5 stars10 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.
Condo in Bronston
4.71 out of 5 average rating, 35 reviews

Lakefront Condo at Woodson Bend Resort

NicoleRating, 5 stars8 months ago
Beautiful condo at Woodson Bend! The kitchen is HUGE as well as the patio! We will definitely stay again!
Top Guest favourite
Condo in Pulaski County
5 out of 5 average rating, 32 reviews

Highly upgraded, luxury condo in Woodson Bend

KristineRating, 5 stars4 months ago
We were there at Thanksgiving time so the busy season was over. It was a beautiful area with lots of deer and other wildlife. The condo was very cosy, clean and updated. Very comfortable beds too! We really didn’t need much in the way of service because everything was already there and we had no issues. The couple things I did ask Holly about were answered immediately! I highly recommend this location, condo and hostess.

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