
Holiday rentals with a pool in Kennebunkport
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Top-rated rentals with a pool in Kennebunkport
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Kennebunkport rentals with a pool
House rentals with a pool

Fantastic Kittery Home with Pool
This was our second time staying at Ned‘s place. Just as Beautiful as it was several years ago. He keeps the property very well maintained and takes pride in making sure we are comfortable and have everything we need for a pleasant stay. Felt right at home!!

Locke Lake Waterfront Escape
Great and relaxing location, close to local amenities. Perfect for small groups, Hillary was awesome to rent from.

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK
I hosted a group of 8 girls here for a bachelorette and we can’t say enough great things about the place. It was clean and exactly how described. There was plenty of parking space for multiple cars. The hot tub was an enjoyable extra amenity. Jey was quick to respond with any concerns or questions. The home was a quick 20 minute drive from downtown Portland.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Angela’s place was wonderful! Very cozy, clean and comfortable, well stocked, close to downtown Portland. Snacks was a nice touch! Angela was very responsive. Hope to come back soon!

Beautiful Lakefront Vacation
Donna is fantastic and if your looking for a charming New England spot this is it! We Are very satisfied with this home.

Fireplaced Mountain King Suite w/Hot Tubs & Pools
Great stay so homey and comfortable has everything we needed staying with two little girls ! Having laundry and kitchen made everything so convenient ! Close to so many things to do was the best vacation we’ve been on would definitely love to come back . Clean and organized everything was easy to find ! Great amenities pool ect !

There's No Place Like Home
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage
The house is beautiful and the views are just breathtaking. From inside the house, you get a beautiful view of the lake and then the porch is amazing. You can kayak, use the paddle board or use the canoe. You can also sit by the lake and enjoy the campfire. The surroundings are very beautiful and peaceful. The host is very responsive, solved all our doubts and was flexible with us during check-in and check-out, which we appreciated very much. At check-in, we were greeted by a great bottle of wine and chocolates, which was a great touch. The house also has a ping pong table, books to read and board games. The kitchen was well stocked with the basics. We had an amazing stay, we highly recommend this property :)
Apartment rentals with a pool

Upscale retreat w/ panoramic White Mountain views
We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

Attitash Studio | 5min to Storyland| Pools
Was a nice peaceful stay for the most part. The pools were nice to swim in although it seems not everyone seemed to want to follow the pool rules. Doesn't help that there were no lifeguards to ensure kids remained safe other than the parents. A few times I saw individuals in the pool water with either glass or an open drink in hand. Saw kids diving into the pool and even witnessed a few hurt themself. But other than that, the hot tub was so lovely to soak in. The arcade room was fun to play in. It was cool to see there was a lot to be able to do in the area for yourself. Definitely wish there was more to do in the area other than the classic tourists spots. A lot of beautiful spots to hike. We ended up checking out Diana's Bath and it was a gorgeous spot to watch cascading waterfalls or have a tiny dip. Would definitely check out this space again and maybe spend a few more days to truly appreciate the environment and mountains ^-^

Spacious Condo-Attitash Ski-Storyland-Saco & More!
Beautiful place to stay! Great amenities for the kids ! Will definitely go back ❤️

Bartlett Condo; Great Views, Resort Access
Would highly recommend this place if you’re in the Conway area or would like to explore all that this area has to offer. Very easy to get to and it’s in a perfect location with great views.

KimBills’ on the Saco
We are a family of four and we stayed for four nights. It was larger than we expected and we were all quite comfortable. We loved that we could ski, swim, and have dinner without getting into our car on an extremely frigid (-17 degree windchill) day! It was a fun atmosphere and we loved our stay!

Intimate Garden Style Condo with Mountain Views
We had a wonderful stay here! We were up for a weekend to enjoy the snow and mountains and appreciated how close it was to everything we planned. We had a snow storm the second night and the grounds maintenance was perfect, we had no problem walking right out the door. We would recommend heading for a stay!

Bartlett N. Conway, NH condo ski near Storyland
We loved our stay and couldn't have felt more at home. Condo has everything you need and the hosts were so kind. Plenty of space for our family of 4 but could easily fit 6. Location is ideal for families to explore all Bartlett has to offer. Highly recommend and can't wait to come back!

An Amazing Mountain Getaway!
My family and I had an amazing weekend. Melissa was very responsive and flexible with checking in/out. Everything was clean, plenty of linens and towels, great location, comfy beds. 10/10. We can’t wait to be back!
Quick stats about holiday rentals with a pool in Kennebunkport
Total rentals
20 properties
Nightly prices starting at
₹9,497 before taxes and fees
Total number of reviews
160 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Hampton Beach
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- North Hampton Beach
- Popham Beach State Park
- Long Beach
- Surfside Beach
- Crane Beach
- Long Sands Beach
- Rye North Beach
- Bear Brook State Park
- Fox Ridge Golf Club
- Wentworth by the Sea Country Club
- East End Beach
- Brunswick Golf Club
- Cliff House Beach
- Palace Playland
- The Golf Club of New England
- Ferry Beach
- Funtown Splashtown USA
- Purity Spring Resort