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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 favorite
A spacious deck features a hot tub with a privacy screen and comfortable seating arrangements. The outdoor furniture includes a sectional sofa and a low coffee table, all set under a large orange umbrella. Lush greenery surrounds the area, providing a sense of seclusion.
Home in Biddeford
4.97 out of 5 average rating, 32 reviews

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

Morgon-AshliRating, 5 stars2 weeks ago
Gorgeous house, peaceful area, a great back deck with pool and hot tub! Jey was a great host, very helpful and quick response time. The house was very clean and put together. I would totally recommend staying at jeys house!!
Superhost
Home in Bartlett
4.9 out of 5 average rating, 200 reviews

Fireplaced Mountain King Suite w/Hot Tubs & Pools

HeatherRating, 5 stars1 week ago
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 !
Superhost
A spacious living room features a large sectional sofa with colorful accent pillows. A wooden coffee table sits in the center. Natural light fills the space through multiple windows, while a spiral staircase leads to an upper level. A mounted television is positioned above the fireplace.
Home in Arundel
5 out of 5 average rating, 3 reviews

Spectacular 3 Bed Resort Cottage

RebeccaRating, 5 stars10 months ago
Beautiful home in a quiet, family-friendly community. We loved being able to walk up to the pool and play in the game room in the main clubhouse area. The house is a short drive to downtown Kennebunkport and local beaches. It is a quick 30 minute drive up to Portland. Our daughter loved sleeping in the private bedroom upstairs. The kitchen was fully stocked with appliances. The space was immaculate when we arrived. Steve was responsive to any needs we had during our stay. A great find!
Superhost
A campfire burns brightly near the shoreline, with flames reflecting off the calm water. Adirondack chairs are positioned nearby, providing a serene view of the sunset over the lake, framed by trees and a rocky edge.
Home in Barnstead
4.89 out of 5 average rating, 124 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

AndresRating, 5 stars1 month ago
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 :)
Guest favorite
A living area features a comfortable gray sofa and an accent chair with a small ottoman. A light-colored coffee table sits in the center. Two windows allow natural light to brighten the space, while a wall-mounted television adds to the room's functionality.
Home in Saco
4.92 out of 5 average rating, 13 reviews

Cottage ten minutes from beach

VincentRating, 5 stars3 weeks ago
Great place to stay! Clean and comfortable. Excellent location, close to many restaurants, and other activities!
Guest favorite
An aerial view of a spacious backyard showcases a well-maintained heated pool surrounded by a patio area with seating. Lush greenery and trees frame the property, enhancing the outdoor space, while a shaded fire pit area and landscaped garden beds are visible.
Home in Stroudwater
5 out of 5 average rating, 11 reviews

The Hill's on Buttonwood

DanielRating, 5 stars7 months ago
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown
Top guest favorite
A spacious living area features large windows that allow natural light to fill the room, while providing views of the surrounding landscape. A stone fireplace is centered among wood-paneled walls, complemented by a modern sectional and a leather sofa arranged around a coffee table.
Home in Bethel
5 out of 5 average rating, 17 reviews

Pet Friendly Home, Ski Storage Room, HotTub, Sauna

JamesRating, 5 stars2 weeks ago
This place was one of the best i’ve stayed in, and Joe & Colleen thought of everything you could possibly need to feel beyond comfortable. They were extremely kind and responsive hosts, and the space made us feel like royalty. What a fantastic experience, better than the pictures, we never wanted to leave the home. We enjoyed walking the neighborhood with our dogs, and did i mention the hosts left dog bowls, beds, toys, waste bags and more? This home is less than 10 mins from bethel village, 15 from sunday river, and 20 from beautiful grafton notch state park. Overall, the house was amazing, the sauna hot tub and heated pool were fantastic, and we would stay again in a heartbeat
Superhost
A log cabin is nestled among tall trees on a gentle slope. Large windows create airy views from the exterior, showcasing a front deck that extends along the house. The natural surroundings provide a peaceful and serene setting.
Home in Peru
4.95 out of 5 average rating, 218 reviews

the lake house

CarlaRating, 5 stars5 months ago
We had a lovely time at the cabin. Close to skiing yet peaceful and relaxing. We thoroughly enjoyed our stay ! Thank you!

Condo rentals with a pool

Guest favorite
An outdoor swimming pool is surrounded by a sunbathing area with numerous lounge chairs arranged neatly. A clubhouse with a red roof is visible in the background, bordered by lush greenery and trees that provide a natural setting.
Condo in Bartlett
4.87 out of 5 average rating, 303 reviews

Attitash Studio | 5min to Storyland| Pools

JasmineRating, 5 stars1 week ago
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 ^-^
Guest favorite
A large outdoor pool area is surrounded by lounge chairs in vibrant colors. The pool is complemented by neighboring buildings with multiple windows, providing a welcoming atmosphere. The concrete patio offers ample space for relaxation and sunbathing, with a barbecue area visible in the background.
Condo in Wells
4.85 out of 5 average rating, 187 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars1 week ago
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
Guest favorite
A cozy living area is illuminated by warm lighting, featuring a comfortable sofa adorned with decorative pillows. A coffee table holds potted plants, complementing the wooden furniture. The adjacent kitchen is equipped with modern appliances and counter seating, blending functionality and comfort.
Condo in Glen
4.92 out of 5 average rating, 462 reviews

Across from Storyland & in the Heart of the Mtns

MonamiRating, 5 stars3 weeks ago
Beautiful place, has everything you might need. Very convenient location , close to storyland, restaurants and convenience stores . The restaurant recommendations from the host were great
Guest favorite
An indoor pool area is showcased with a spacious layout featuring large windows that allow natural light to fill the room. Several lounge chairs are arranged around the pool, providing a relaxing environment. The wooden ceiling adds warmth to the setting.
Condo in Bartlett
4.87 out of 5 average rating, 149 reviews

Spacious Condo-Attitash Ski-Storyland-Saco & More!

CristinRating, 5 stars1 week ago
Beautiful place to stay! Great amenities for the kids ! Will definitely go back ❤️
Guest favorite
An indoor pool area is shown with large windows allowing natural light to fill the space. Several individuals, including adults and children, are engaged in swimming and playing. Comfortable seating is available along the poolside, and steps lead to the water.
Condo in Bartlett
4.84 out of 5 average rating, 357 reviews

Quiet Condo Close to Shopping and Attractions

KeighleyRating, 5 stars3 weeks ago
Amazing place! Clean, lots of amenities, and the place had all the basics you could need! I will definitely be referring friends and returning for future trips!
Guest favorite
A comfortable living area is presented with a dark leather sofa and two wooden lounge chairs. Soft lighting from lamps creates a warm ambiance. A coffee table stands at the center, and large sliding glass doors open to a view of the outdoor grounds.
Condo in Glen
4.89 out of 5 average rating, 264 reviews

Intimate Garden Style Condo with Mountain Views

MollyRating, 5 stars4 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
An outdoor heated pool is framed by lounge chairs, providing a space for relaxation. The pool reflects the two-story building behind, with large windows visible. Umbrellas offer shade on sunny days, and well-maintained grass surrounds the pool area.
Condo in Wells
4.76 out of 5 average rating, 134 reviews

Generic Two Bedroom - Stair access only

DeysiRating, 5 stars3 weeks ago
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.
Top guest favorite
A well-maintained outdoor pool is enclosed by a chain-link fence, featuring a spacious deck with lounge chairs and umbrellas. Lush greenery surrounds the area, enhancing the tranquil environment. A pool cleaning net rests on the pool deck, indicating regular maintenance.
Condo in Conway
4.96 out of 5 average rating, 110 reviews

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

RachelRating, 5 stars5 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!!!!

Quick stats about vacation rentals with a pool in Cumberland

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 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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