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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
4.71 out of 5 average rating, 14 reviews

Private pool, 8 person Hot tub 6 Bedrooms

JanellRating, 5 stars8 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, 7 reviews

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

CourtneyRating, 5 stars2 weeks ago
Ellie’s place was exactly as is in the listing! It’s absolutely beautiful! Pictures doesn’t do this place any justice. The host was fast to respond each time I reached out the pool table and the projector screen were great additions! We had so much fun!! We will deff be back!
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!
Superhost
Home in Burnside
4.67 out of 5 average rating, 6 reviews

Blue Lagoon at VillagerResort,Pool,Boat slip/dock

MatthewRating, 5 stars8 months ago
Great place, super convenient to everything and my kids loved the trolley!
Home in Burnside
4.56 out of 5 average rating, 88 reviews

Lakeside Retreat/ Jacuzzi and Private Pool

ShelbyRating, 5 stars2 weeks ago
Hot tub was nice and the place was clean! Would stay here again!
Home in Liberty
5 out of 5 average rating, 3 reviews

Teddy Hill Homestead

KaitlinRating, 5 stars5 days ago
Great rental. The shower is a roll-in -- very friendly to different physical abilities. The beds were comfortable, though the king size bed might be too soft for some. Plenty of hot water. Lots of space to spread out.
Guest favourite
Home in Burnside
4.87 out of 5 average rating, 98 reviews

Cozy Cumberland Lakeview Shangri-la

JoshuaRating, 5 stars1 month ago
Very quiet and peaceful location that felt like a retreat, but also close enough to town and nearby attractions. My family of 6 had a great mini Spring Break getaway.

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 stars22 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 stars8 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 stars10 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 stars9 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 stars5 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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