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, 41 reviews

Upscale OOB Beach House | Seasonal Heated Pool

BonnieRating, 5 stars6 days ago
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.
Guest favorite
The backyard features an above-ground pool surrounded by a spacious deck, offering ample seating and relaxation areas. A shaded dining space is visible under an umbrella, while the two-story colonial home stands in the background, framed by lush greenery.
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars8 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 favorite
A spacious living area features a stone fireplace, surrounded by comfortable seating options and rustic decor. Natural wood accents are present in the beams and walls, while a Christmas tree adds a festive touch. Large windows provide views of the outdoors.
Home in Fryeburg
4.97 out of 5 average rating, 30 reviews

The Lodge at Hidden Pines

JordannaRating, 5 stars3 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.
Superhost
Home in Bartlett
4.9 out of 5 average rating, 200 reviews

Fireplaced Mountain King Suite w/Hot Tubs & Pools

HeatherRating, 5 stars4 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
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 stars9 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, 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 :)
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

Condo rentals with a pool

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 stars6 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 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 stars4 days 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 stars2 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 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 Glen
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 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 stars2 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!!!!
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 Glen
4.93 out of 5 average rating, 268 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

    G$8,366 GYD 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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