
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!!

210 Sea Castle Circle
Very nice place, everything was clean and smelling good, we felt right at home! Comfortable beds except the single one which we could feel the springs. Expensive parking everywhere near the beach, be advised, but free parking at the house. Everyone at the place was friendly. The only thing mmissing would be coffee pods, for the rest, everything was there!

Upscale OOB Beach House | Seasonal Heated Pool
This was the perfect home base for exploring various parts of the Maine coast. Beds were comfy, and each room had a wall unit to make it the temperature you like. Our kids loved being upstairs in the 3 beds room and having their own space. WiFi worked great, and that was with 7 of us on it doing various things - adults working, kids streaming. Would definitely stay here again.

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
The house was spotless and centrally located for what we wanted to do in southern Maine. It was well stocked with quality toilet paper, napkins and Kleenex. We had plenty of towels for the hot tub and pool. It is updated and well taken care of. The hosts were extremely helpful and we didn’t see them at all, so the place felt very private. This was an amazing house and our kids had so much fun in the pool and playing corn hole on the large deck. Would recommend this house for families and couples in a heartbeat!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Angela was a fantastic host, responding quickly to any questions. The home was nice, close to downtown, and a HUGE yard for the dogs

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!

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 !
Condo 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!

Starfish Condo Wells Beach
This was a great find and enjoyed our 3 week there - We got to meet a few neighbors, and they were very nice as well - Very close to restaurants and Wells Beach - WIFI worked great as I work from home and the tip about leaving the second car at the Wells Transportation Center helped a lot ! Danielle was great with communication and rules - We would stay here again

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!

An Amazing Mountain Getaway!
Peter & Melissa were excellent hosts, they were extremely responsive and super helpful! 10/10 would stay at their place again! It was the perfect location and very family friendly, we had a great weekend!
Quick stats about holiday rentals with a pool in Kennebunkport
Total rentals
20 properties
Nightly prices starting at
$170 AUD before taxes and fees
Total number of reviews
160 reviews
Family-friendly rentals
10 properties are a good fit for families
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi 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
- Cliff House Beach
- East End Beach
- Brunswick Golf Club
- Palace Playland
- The Golf Club of New England
- Ferry Beach
- Funtown Splashtown USA
- Purity Spring Resort