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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 backyard is captured, featuring a seasonal swimming pool bordered by a stone patio. A grassy area is visible, accented by trees and shrubs. In the distance, a playset is seen, providing a space for outdoor activities. The sky has a gentle evening glow.
Home in Kittery
4.95 out of 5 average rating, 40 reviews

Fantastic Kittery Home with Pool

BarbaraRating, 5 stars5 months ago
The house was perfect for my family and I- plenty of open space for the kids to play and a great yard- even in December with cold weather the kids loved the play gym outside!! The location was amazing with lots of things to do within a few minutes and the food scene was great. Thanks to Ned for a spotless home and great amenities!! We can’t wait to come back in the summer to use the pool!!
Guest favorite
The living area features a spacious sectional sofa complemented by a matching ottoman. Light wood flooring contrasts with a large area rug displaying a star motif. Artwork depicting coastal scenes adorns the walls, while windows let in natural light, illuminating the adjacent dining table.
Home in Old Orchard Beach
4.98 out of 5 average rating, 40 reviews

Upscale OOB Beach House | Seasonal Heated Pool

SavannahRating, 5 stars2 weeks ago
Jason was a fantastic host—responsive, helpful, and easy to communicate with. Although we encountered a few minor issues during our stay, he responded immediately and went above and beyond to ensure everything was resolved quickly. The space itself was absolutely beautiful and made for a wonderful stay. I would highly recommend this place to anyone and hope to return in the future!
Superhost
Home in Bartlett
4.9 out of 5 average rating, 200 reviews

Fireplaced Mountain King Suite w/Hot Tubs & Pools

HeatherRating, 5 stars3 days 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
An outdoor deck is presented, equipped with a round table and several chairs beneath a large umbrella. Surrounding trees provide shade, while distant views of Lake Winnipesaukee are visible, creating a serene outdoor dining space.
Home in Gilford
5 out of 5 average rating, 3 reviews

Coolest Condo on the Lake!

MicheleRating, 5 stars1 week ago
We enjoyed our short, but lovely stay at the lake! Home was beautiful and warmly decorated. Comfy beds and set up so nicely! View of lake was so nice and it was hard to leave the deck. We loved the peace and quiet, relaxing vibe! Loved the closed in porch too! Enjoyed pickleball so easily accessible and pretty walk to the lakefront to relax. Wish we could have stayed longer, but rain made it easier to leave. We had magical weather our full day! We hope to return to this special area and home. Loved the market so close though! Thank you!!
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, 123 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 :)
Superhost
A classic beach house is situated amidst lush greenery, featuring a charming wraparound porch. The two-story structure is accentuated by large windows and a balcony above. A clear blue sky complements the inviting landscape, creating a serene setting just steps from the beach.
Home in Kennebunkport
4.96 out of 5 average rating, 26 reviews

Lovely Beach house in GRB - Heated pool!

SophieRating, 5 stars2 weeks ago
Great stay with our family of 6! Lots of space for everyone!
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 Portland
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

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 stars3 days 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 stars5 days 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
An inviting in-ground pool is surrounded by a spacious patio, offering numerous lounge chairs for relaxation. Lush green lawns and trees frame the pool area, while buildings are visible in the background, contributing to a serene outdoor setting.
Condo in Bartlett
4.92 out of 5 average rating, 461 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
Top guest favorite
Condo in Bartlett
4.99 out of 5 average rating, 142 reviews

KimBills’ on the Saco

SaraRating, 5 stars3 months ago
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!
Guest favorite
A tranquil pool area is surrounded by lush greenery. Comfortable lounge chairs are arranged on the pool deck, along with umbrellas for shade. The clear water reflects the tree canopy overhead, creating a serene atmosphere for relaxation.
Condo in Bartlett
4.89 out of 5 average rating, 142 reviews

Cozy 1 BR Resort Condo; Fireplace; Amazing views

MarcRating, 5 stars2 weeks ago
Great long weekend stay! Location perfect for trail/gravel biking, hiking, waterfall searching, and fly fishing! Perfect for 2…..great views to Doublehead and black mts. Accommodations were perfect. Kitchen stocked with essentials, large bathroom w separate jet tub…..and adequate hot water capacity to run it. Recommend highly.
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 Bartlett
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!
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!!!!
Guest favorite
A seasonal outdoor pool is surrounded by landscaped gardens and lounge chairs, showcasing stunning mountain views. Lush greenery and colorful flowers frame the area, while a cozy seating area is visible in the distance beneath the clear blue sky.
Condo in Bartlett
4.93 out of 5 average rating, 267 reviews

An Amazing Mountain Getaway!

KelseyRating, 5 stars1 week ago
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 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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