
Holiday rentals with a pool in Cumberland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cumberland
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Cumberland rentals with a pool
House rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Maine Home
Clean , comfortable...home away from home...would definitely rebook if I revisit Old Orchard Beach Elisa

Faith Lane with community pool
We had a wonderful stay- place was pristine and welcoming, looks exactly like the photos. Of course being closer to water is always great and can’t beat it for the price. Many OOB hotels leave much to be desired and are outrageously expensive for what you get. After some less than stellar experiences, to be somewhere clean, free of bugs and animals was a relief. Easy uber ride or trolley to boardwalk. Definitely would rent there again!

Pleasant River 3 bed | 2 bath, Pool, Hot Tub
Josh's place was great. close to our activities, not far from restaurants. josh was very quick to respond and remedy the only issue we had, which was with the hot tub. the only thing we didn't have that I personally wish there was, was a broom. the place was clean but I hate feeling dirt on my feet inside, so I bought a broom, but that was my decision. great place, thanks Josh

Oceanfront Cottage 1
We had a wonderful time! Going during off season was very peaceful and quiet will definitely book again in the future!

2BR, Sea & Relax w/ Wells Reserve View
Cottage 2 br, well equipped kitchen and nice extra porch enclosed and furnished beachy decor. Backyard comfortable adirondack chairs for sitting. Near to beach with free parking if spots are available. plenty of restaurants and grocery nearby. Last cottage in the row and was quiet. Pool and hot tub on property. Would rent again.

Heated POOL|Views|HotTub|Sauna|2mi to SR Golf Club
Eshi was very responsive when needing help with the sauna instructions and other things! Beautiful views and a great place to host a sweet 16 🩷

Spectacular 3 Bed Resort Cottage
This cottage in Arundel was just perfect! Beautiful, private, quiet setting, and just a short drive to all the best beach towns! We absolutely loved everything about it! Jaime & Susan

Cottage ten minutes from beach
Great place to stay! Clean and comfortable. Excellent location, close to many restaurants, and other activities!
Condo rentals with a pool

Cozy Beach Condo in Wells - Hot Tub & Pool!
Thank you for a great stay, Kathleen! My husband and I were celebrating our anniversary and both of our birthdays that week and needed a little get away. This was perfect for us. I wish the weather was better, but you can’t do anything about that. We ate great food, went to a movie, shopped, went to the Nubble lighthouse and more. We would definitely use Kathleen again. She also made arrangements to have my favorite hoodie sent back to me as I mistakenly left it on the back of the door. Great host and super cute place!

Don’t miss out, book for Fall NOW!
This AirBnB was a perfect winter vacation escape. It had everything we needed for our two families. The kitchen was so well stocked and we were never without. Great set up. My 5 year old begged to live there forever! We can't wait to come back!

Lovely Seaglass Studio, Pool, Walk to Everything!
Denise is an outstanding host! We couldn't believe that the kitchen was FULLY stocked! from the coffee keurig, to the teaspoons and everything one would need to cook dinner or breakfast or both. We were super impressed with the quality of kitchen items and how clean everything was. Even the bathroom was stocked with the "little things" like individual make up remover packs which I was most thankful for as I had forgotten mine! The linens were beautiful and there were 3 choices of pillows for the bed! We loved that she also had clear instructions regarding towels, checking out and the use of the keyless entry. The decor is warm and welcoming...very inviting. We loved that we could walk to everything in Ogunquit and Perkins Cove. Our stay in Maine was just wonderful and we would definitely book with Denise again.

Two-Bedroom Condo on the Wells/Ogunquit town-line
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Relaxing Beachside Condo with Pool at Wells Beach
Julie’s place was very nice and very clean. The location was great, right across the street from the ocean. The kitchen was well-equipped and there was even a small basket of treats. Julie responded very quickly to any messages we sent. We would highly recommend this place.

Generic Two Bedroom - Stair access only
Great place to stay for our family of 4. I asked for 3 beds and that request was made possible. I enjoyed the area and it was quiet and peaceful place to rest after walking around the beaches and or state parks. Amenities were very good and communication with the check in team was excellent.

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104
Jennifer's place is AMAZING! First, it's steps away from the ski lift. Not only can you make first tracks, but stopping for lunch/breaks/warm-up is super easy - ski to your door! Getting in was a breeze: pull up, get the FOB, grab a luggage rack and park in the designated spot by the door and you're done. No long walks hauling ski gear through endless parking lots. The condo is spacious, super comfortable, and great for hanging out. We had 4 adults and 4 kids (8-11) and we had plenty of room for game nights, dinners, and lounging after a long ski day. The bathrooms are big (and even a jet tub for bubble baths). And immaculately clean. Full kitchen equipped with everything you need. So great to have washer/dryer to get gear ready for the next day. And the heated pool/hot tub is a short walk, both are big and a hit with the kids and adults. And did I mention how clean the place was? The unit is on the end to give extra privacy and easy access. Six stars!

Cozy, clean, 2nd floor condo in Conway, NH!
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!!!!
Quick stats about holiday rentals with a pool in Cumberland
Total rentals
20 properties
Nightly prices starting at
$67 NZD 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
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Popham Beach State Park
- Long Beach
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Diana's Baths
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Cliff House Beach
- East End Beach
- Brunswick Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Ferry Beach
- Funtown Splashtown USA
- Cranmore Mountain Resort
- Purity Spring Resort
- King Pine Ski Area
- Dunegrass Golf Club