
Holiday 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.
Holiday 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

Treehouse Farm - Sebago

Coastal, 3 bedroom, 2 bath home with pool!

Willow Creek Homestead Indoor Pool Lake Access

Upscale OOB Beach House | Seasonal Heated Pool

New Listing! Pool, Hot tub & Lakes! Mins to Sebago

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront

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

Our Beach House Getaway
Condo rentals with a pool

LUXURY OCEANFRONT CONDO Best Location on the beach

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

Condo in Old Orchard Beach

Ocean View Studio Beach Condo

Maine, Beach front Condo! Vacation hotspot!

Gorgeous OceanView condo at Grand Victorian - #301

Steps to Beach, Pier, Park | Condo with Pool • 8

Lovely 2 bedroom condo, 400 ft from sandy beach
Other holiday rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Maine Home

TreeBear Cottage | Waterfront | Private Dock

A mile from the ocean, brand new, clean and comfy.

Seaside Condo Old Orchard Beach

Luxury Nature Vacation Sanctuary in Portland

Moose Pond Cottage - 3 mins to Pleasant Mountain!

Charming Chalet 3 min to SKIING & PVT beach access

Peaceful Waterfront Apt w/ Deck, 22 Mi to Portland
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- Rentals with pools Maine
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Story Land
- Scarborough Beach
- Long Sands Beach
- York Harbor Beach
- Attitash Mountain Resort
- Popham Beach State Park
- Popham Beach, Phippsburg
- Pemaquid Beach
- Diana's Baths
- Pemaquid Point Lighthouse
- Dunegrass Golf Club
- East End Beach
- Funtown Splashtown USA
- Crescent Beach State Park
- Laudholm Beach
- Parsons Beach
- Cliff House Beach
- Ferry Beach
- White Lake State Park
- Wolfe's Neck Woods State Park
- Short Sands Beach
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