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Chebeague Island Pet Friendly Rentals

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    $195 Average
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    Don't let other travelers get your favorite Chebeague Island area vacation rental. You're so close to securing your perfect getaway. Book today.
    12 Matching Rentals in the Chebeague Island AreaView all 58 rentals
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    The following rentals are within 10 miles of Chebeague Island.
    WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!1 / 72
    (2)Excellent
    South Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Large Home Walk to Beach! Close to all amenities!1 / 26
    (9)Excellent
    South Portland
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Internet Access
    • Satellite TV
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll be only one block from Willard Beach at this two-bedroom South Portland condo, a charming and comfortable getaway with a dog-friendly interior, a private outdoor deck, and a wonderful location near lighthouses, shops, restaurants, and the gorgeous shores of Casco Bay. The building, which...
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    Location Information
    South Portland, Maine 04016
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Grill
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a revitalizing retreat to the charming city of Portland when you stay at this lovely vintage condo. You'll have updated amenities inside, plus a deck and gas grill, and you'll be in close proximity to lots of restaurants nearby in Willard Square. Conveniently located in Willard Square, this...
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    South Portland, Maine 04106
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Dog-friendly home with a game room and patio, close to parks, trails & downtown!1 / 27
    (1)Excellent
    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Parking
    • Washer
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2017
    We had a fantastic time at this property. It was close to downtown, barely a 10 minute drive by car to a wide variety of restaurants, shopping, grocery stores, and parks. The...
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    About this property
    Discover classic New England charm within walking distance of downtown Portland at this three-bedroom home, where you'll enjoy a private patio, a lovely remodeled kitchen, and a wonderful location close to dining and shopping. Built in 1910, this dog-friendly home is located in a quiet neighborhood...
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    Portland, Maine 04103
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The Willard Beach House (Dog friendly!)1 / 13
    (1)Excellent
    South Portland
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2017
    This was a find. Charming perfect beach house, literally steps from the beach. And dog friendly. Darrell and Judy were perfect hosts, very helpful. We will definitely be back.
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    About this property
    This unique ocean side carriage house is just one house from the ocean. It has one bedroom with a king size bed. A full bath and kitchen. All linens, plates, utensils and glassware included. Air conditioned. Our beach is a quiet, sandy, mile long neighborhood beach on Casco Bay, with views to the...
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    South Portland, Maine 04106
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Willard Beach Get Away - Dog Friendly1 / 13
    (1)Excellent
    South Portland
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Grill
    • Terrace
    • Balcony
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2017
    Great location for visiting all the Portland sights. Located in a quiet section of South Portland just one house from the beach. The owner was friendly and helpful at all stages...
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    About this property
    Perfect for a Maine summer vacation. This completely renovated, 400 sq foot studio apartment is one house away from Willard Beach, 4 blocks to Willard Square, 1 mile from downtown South Portland, and a 5 minute drive to downtown Portland, ME. The apartment has a full bath, a kitchenette, air...
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    Location Information
    South Portland, Maine 04106
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    South Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • DVD Player
    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE TURNKEY ADVANTAGE Our property is TurnKey Rental Certified. All photos, amenities, calendar, and rates are 100% accurate. We will notify you proactively when early check-in / late check-outs are possible and you'll receive the comforts of home with a starter supply of shampoo, soaps, paper...
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    Location Information
    South Portland, Maine 04106
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1,400 SF of Living Space with a Fenced back yard Fantastic space with high ceilings, modern kitchen and room for 8. Washer & Dryer on site, close to all things Portland without being directly in the bustle of downtown. Great for families with dogs or folks in town for all of the amazing music...
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    Location Information
    Portland, Maine 04103
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Bailey Island
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Patio
    • Satellite TV
    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Restored oceanfront 1910 shingle-style house with private pool, spa, private beach, and incomparable views in all directions. Six bedrooms, four full baths, two fireplaces, large updated kitchen and oceanside porch. This house has all its original charm and authentic details including natural...
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    Bailey Island, Maine 04003
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Falmouth
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adorable, quaint and ideally located Maine Beach cottage. Fully furnished with updated furniture, comfortable beds, and all the necessary amenities. Steps from private beach - bring your kayak, paddleboard or other water craft or just relax and watch the sailboats on the Bay and go fishing from the...
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    Location Information
    Falmouth, Maine 04105
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Chebeague Island Flight and Weather Info
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    Portland Intl Jetport
    11.4 miles from Chebeague Island
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