Vacation rentals with a pool in Cumberland

Find and book unique homes with a pool on Airbnb

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Popular amenities for Cumberland rentals with a pool

House rentals with a pool

Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 33 reviews

Love OOB! NEW 3 BR, 2.5 BA Maine Home

LoriRating, 5 stars8 months ago
Heather’s place was by far the most well maintained and clean Airbnb our family has ever stayed in. She was responsive and kind with all our needs. The pool was conveniently located right across the road and a beautiful place to spend the warmer day. Walking to the OOB trolly, seafood restaurants and the best ice cream place we’ve visited yet. We look forward to making Heather’s place and a trip to the Maine coast an annual family vacation.
Superhost
Home in Wells
5 out of 5 average rating, 3 reviews

210 Sea Castle Circle

VincentRating, 5 stars7 months ago
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!
Guest favourite
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars6 months ago
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!
Top guest favourite
Home in Biddeford
5 out of 5 average rating, 27 reviews

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK

AshleyRating, 5 stars7 months ago
Thank you for allowing us to stay at your beautiful home. The photos did it no justice! I can’t wait to be back, we will be stay here again.
Top guest favourite
Home in Fryeburg
4.97 out of 5 average rating, 30 reviews

The Lodge at Hidden Pines

JordannaRating, 5 stars2 months ago
The house was exactly as described and seen in the photos, a large, beautiful, authentic log cabin in the woods. The setting was quiet and beautiful though conviently right off the main road. We enjoyed cross country skiing, ice skating and a sleigh ride in Jackson (about 30 min away) and shopping in North Conway (about 20 min). Eileen made sure we were plowed and shoveled regularly during the snow storm so we enjoyed curling up by the fire and watching a movie on the large tv. My mother in particular enjoyed all the vintage decor which brought back childhood memories.
Guest favourite
Home in Bartlett
4.82 out of 5 average rating, 120 reviews

Walk to StoryLand!Updated Condo! WiFi/Golf/Pool/AC

SHAUNRating, 5 stars3 months ago
Had a quick weekend getaway at Keith's place. Everything was perfect. Easy check in and great communication.
Guest favourite
Home in Portland
4.95 out of 5 average rating, 123 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Kathleen AudreyRating, 5 stars4 weeks ago
My stay was very comfortable. The property was well kept and updated. The beds and furniture were were in perfect condition. Both the house and the grounds were exceptionally clean and well maintained. I would visit again!
Guest favourite
Home in Portland
4.82 out of 5 average rating, 109 reviews

There's No Place Like Home

JeremyRating, 5 stars7 months ago
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!

Condo rentals with a pool

Guest favourite
Condo in Bartlett
4.91 out of 5 average rating, 100 reviews

White Mountains Hiking Dogs Storyland Family

WilliamRating, 5 stars5 months ago
Wife and I had a great time at Fairley’s place. Condo was as advertised, clean with all the utensils you need. The resort has a clubhouse with all great amenities. Location is great! We would definitely like to rent again.
Guest favourite
Condo in Bartlett
4.93 out of 5 average rating, 200 reviews

Bartlett Condo; Great Views, Resort Access

AnnetteRating, 5 stars2 months ago
This is the second time we have stayed at Bill's Condo. We love the location. I think this is one of the very best views in Nordic Village. Also, Bill is one of the best hosts that I have worked with. We had early check in which was great. The condo itself is very well stocked and had everything that we needed. Great Kitchen, comfortable bed, 2-person jet tub, and fireplace makes the condo very cozy and inviting. Hope to stay again soon.
Guest favourite
Condo in Bartlett
4.89 out of 5 average rating, 264 reviews

Intimate Garden Style Condo with Mountain Views

MollyRating, 5 stars2 months ago
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!
Superhost
Condo in Wells
4.75 out of 5 average rating, 126 reviews

Generic Two Bedroom - Stair access only

Rose-MarieRating, 5 stars2 months ago
The condo was very clean, tasteful decorated. Beds were comfortable. Loved the big table to play games and the living room was cozy for the evening and morning chats. Pretty views.
Top guest favourite
Condo in Conway
4.96 out of 5 average rating, 110 reviews

Cozy, clean, 2nd floor condo in Conway, NH!

RachelRating, 5 stars4 months ago
A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!
Superhost
Condo in Bartlett
4.83 out of 5 average rating, 270 reviews

Peaceful Condo Near Storyland & Attitash Skiing

PalakRating, 5 stars3 weeks ago
Very clean and relaxing place. Felt like home and will definitely visit back again. The host is very responsive and had clear instructions of everything.
Guest favourite
Condo in Bartlett
4.95 out of 5 average rating, 100 reviews

Mountain views! Condo in amazing Nordic Village!

VictorRating, 5 stars4 weeks ago
I stayed one night at Erics’ AirBnb with my girlfriend. It was amazing. Everything was very clean and it was exactly what the photos showed. The jacuzzi and views were definitely a highlight. It was 10 minutes away from Downtown North Conway which was really nice as well. Eric was very helpful and friendly, He responded to questions and comments very efficiently and was very caring. We had an amazing stay, I would 100% stay here again in the future. I highly recommend. Thank you!
Guest favourite
Condo in Bartlett
4.84 out of 5 average rating, 199 reviews

Cozy Mountain Getaway For All Seasons

JulieRating, 5 stars3 months ago
We had a great day! The place was perfect for our small group, and very convenient to the mountains for skiing. The condo had all the little things needed. And it was very comfortable. I would definitely book again.

Quick stats about vacation rentals with a pool in Cumberland

  • Total rentals

    20 properties

  • Nightly prices starting at

    $55 CAD before taxes and fees

  • Total number of reviews

    320 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore