Vacation rentals with a pool in Cumberland County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cumberland County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Cumberland County rentals with a pool
House rentals with a pool
Home in Old Orchard Beach
4.98 out of 5 average rating, 80 reviewsFaith Lane with community pool
Home in Old Orchard Beach
5 out of 5 average rating, 27 reviewsUpscale OOB Beach House | Seasonal Heated Pool
Home in Windham
New place to stayCozy Nature Escape w/Pool!Mins to Sebago Lake&More
Home in Biddeford
5 out of 5 average rating, 27 reviewsPool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK
Home in Cumberland
5 out of 5 average rating, 14 reviewsHeatdPool&OceanAccess|15Min2Portland|FirePit|Games
Home in Standish
4.94 out of 5 average rating, 50 reviews6BR+ Retreat on 3 Acres Near Lake w/AC +Pets OK
Home in Windham
4.73 out of 5 average rating, 11 reviewsGorgeous Maine House Close to Sebago Lake
Home in Bridgton
4.89 out of 5 average rating, 46 reviews3 mins to Pleasant Mt/Moose Pond w/hot tub & sauna
Condo rentals with a pool
Condo in Old Orchard Beach
4.78 out of 5 average rating, 9 reviews30 second walk to Beach- Pool-Outdoor Shower
Condo in Old Orchard Beach
4.91 out of 5 average rating, 11 reviewsGrand Victorian Ocean Rentals Oob310
Condo in Old Orchard Beach
5 out of 5 average rating, 15 reviewsLUXURY OCEANFRONT CONDO Best Location on the beach
Condo in Old Orchard Beach
4.81 out of 5 average rating, 48 reviews*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM
Condo in Old Orchard Beach
4.83 out of 5 average rating, 35 reviewsMaine, Beach front Condo! Vacation hotspot!
Condo in Old Orchard Beach
4.82 out of 5 average rating, 11 reviewsFamily Vacation Home walking distance to Beach
Condo in Old Orchard Beach
4.78 out of 5 average rating, 37 reviewsGorgeous OceanView condo and Grand Victorian - #301
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