Beautifully located five bedroom, three bathroom cottage with stairs to the rocks below and the ocean, incredible water views and great home-base for your vacation adventures!

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Guests 10
Bedrooms 5
Bathrooms 3
Allows Pets Yes


Piffi Biff is a beautiful cottage located on the historic Southport Island on the Boothbay peninsula. With incredible views of the Atlantic Ocean, Squirrel Island, Boothbay Harbor, Burnt Island, you will also see porpoises, whales, migratory shore birds, sailboats, yachts and lobster boats! The endless parade of nature- made and man-made oceanic wildlife and vessels will provide endless entertainment! Want to get in the picture too?

Need more room? Right next door is Pine Cliff Dweller, a 2 bedroom, 2 bathroom cottage with a private dock and float. Both cottages can be rented together, making a perfect setting for a reunion, girls get-a-way or extended family vacation!

Bring your own kayaks or rent locally. Launch from the association's dock and float just a short walk from your cottage. Piffi Biff is a great home-base for your ocean adventures! Don't sit home and "pine" for Maine. Piffi Biff is located in the Pine Cliff section of Southport Island, only a couple of miles from Boothbay Harbor. This is a perfect spot to see some of the schooners go by during Windjammer Days in Boothbay Harbor! Rent or bring your own bikes and explore this quaint little island, bike over to Southport Beach, enjoy lunch from the Southport General Store or Sunday Brunch at Newagen Seaside Inn. Don’t forget your camera as you explore this little slice of heaven!

Experience Maine like a native. Visit our local farmers market, farms stands and farms to buy local and buy fresh. Don't forget the seafood. Lobster abounds in this area and can be purchased just a short distance away at Robinson's Wharf.

Gorgeous views of the ocean are the hallmark of this classic Maine summer cottage. The large living room has a field-stone fireplace to be enjoyed by all along with the incredible views! A dining room and breakfast room offer even more visual delights. A covered open deck offers another dining options, as well as a place to just sit and take it all in, sights, smells and sounds.

Along with the living and dining areas, the main floor includes one bedroom with a single bed, a half bath and a master bedroom with a Queen Bed and en-suite ¾ (shower) bathroom.

The second floor has two bedrooms, each with a King bed and a third bedroom with three single beds. There is also a full bathroom with a stand-up shower and a separate soaking tub.

1st Floor: One bedroom with a Single Bed. One bedroom with a Queen Bed.
2nd Floor: One bedroom with a King bed overlooking the ocean, Second bedroom with a King Bed. A bedroom with three single beds.

1st Floor: ½ Bath and en-suite ¾ Bath (shower)
2nd Floor: Newly updated and renovated full bathroom with a shower and separate soaking tub.

Peruse our web site for local vendors, eateries and activities. Replete with all things vacation; if you can think of it, our site most likely covers it! Be sure to reach out to us if you need any help creating the perfect vacation!

Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993.
Cottage Connection was one of the first vacation rental companies in the Mid-coast region of Maine. Jeff and Audrey Miller, who own three vacation rental homes themselves had an aha moment when they realized they could not find anyone who ‘got it’ to manager their rentals for them. Since 1993 they have been trusted by homeowners and vacationers to “connect” each family with the perfect cottage for their vacation. As Audrey puts it; “The home they stay in becomes a personality, a part of their lore when a family connects with the right cottage. Whether they want a rustic cabin in the woods or a high-end ocean bungalow, the right setting sets the tone for the entire vacation.” Learn more about how Cottage Connection can help make your vacation perfect!

The Boothbay Peninsula is a beautiful region rich in culture, history, all things nautical and of course its own unique niche in nature. The area offers ample opportunities for biking, kayaking, canoeing, fishing, charters and guided cruises, spas, golf, mini-golf, bowling, museums, antiquing, hiking and walking trails. We have the Maine State Aquarium, the Coastal Maine Botanical Gardens and the Boothbay Region Land Trust with its 30+ miles of pet friendly trails in protected areas. For a more comprehensive list of local offerings Click Here!

Southport Island is a hidden treasure on the Boothbay Peninsula. Two miles from Boothbay Harbor, you cross the bridge onto the island and feel the world change around you. You know you are on vacation. Small sandy beaches, large expanses of rocky shoreline, views of Islands and open ocean, walking, kayaking, fishing and more! This quaint and historical part of Maine is treasured by the few who know of it! From the shore you can see Cape Island once owned by Margaret Hamilton who played the Wicked Witch of the West in the Wizard of Oz. A pair of Ruby Red Slippers is on display at the Island’s library. Hendricks Head Lighthouse and Beach are just a short ride away for those who prefer swimming on more of a sandy beach. Rachel Carson frequented Southport often and mentions the area in her books. The Cuckolds Lighthouse can be seen just off shore. This small little spit of land is rich in history, marine life, unique ecology and more. You will come back again and again!


Pet Friendly
Shared dock and float (association owned)
Small boat ramp (association owned)
Field Stone Fireplace, wood is not provided by owner
Covered Deck
Enclosed Porch
Gas Grill
TV, Cable
VCR (not a DVD player)
Washer / Dryer
Iron and Ironing Board
Linens Included.
Mooring available upon request and meeting certain criteria
Can be rented in conjunction with Pine Cliff Dweller!

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Write a Review
Broadalbin, US
Reviewed: Jul 13, 2016
Property Manager
morris plains, US
Reviewed: May 13, 2016
Property Manager
In order to get what you really want from your rental, a conversation with somebody "in the know" is essential. Cottage Connection staff members were all very helpful in narrowing down our choices.
Piffi Biff provided a good combination of the items we were looking for: pet-friendly, handicap friendly, and (our preference) and oceanfront property.
Catherine C & Paul
Barnington, US
Reviewed: Apr 4, 2016
Property Manager
Cottage Connection is very reliable and professional. We book with them to avoid problems and surprises!
View & porch!
Rochester, US
Reviewed: Dec 16, 2015
Property Manager
Reviewed: Sep 20, 2014
Property Manager
Chose Cottage Connection to obtain accessible cottage on the water and past positive experience. The staff are professional and accommodating
Piffi Biffs views makes for a wonderful experience. The spacious accommodations, the great and spacious deck!


Check-In Day:  SaturdayJune 24-Sept 5, 2016 (Prime Season Week’s).  See below for shoulder season details

Check-In Time: BEGINS 4:00 PM during prime season

Check-Out Time:  no later than 10:00 AM

Town:     Southport

Body of water:  Atlantic Ocean

Type of Waterfront: Rocks & Ledges

Swimming Area Rating for this property is a…,   0

Piffi Biff does have use of the Association Dock & Float, just a short walk from the home.  It is right on the water, but you do not have water access from the home.

5 – very easy water access, sandy or pebble beach, great for all ages!
4 – Easy water access, may be a pebble beach or grassy shoreline. Still good for all ages, but young children may want water shoes.
3 – Somewhat easy water access with a rocky shoreline, or rocky bottom, not suitable for young children, but fine for older children/adults, water shoes recommended.
2 – Water access only for agile young adults or adults, rocky shoreline or bottom, may be a hill down to the water or subject to strong currents.
1 – Swimming off dock only due to a seawall or rocky/wooded shoreline, owner has provided a swim ladder to make getting in and out of water easier. 
0 – not a waterfront property.

Privacy rating for this property is a…,   2

5 – very private, secluded location, lots of protection from trees, cannot see any neighbors from the house, not close to any roads, long driveway.
4 – Private location, protection from trees, neighbors a comfortable distance away, not close to any roads.
3 – Still in a quiet location, but one neighbor close by, little protection from trees, may be close to a road.
2 – Semi-quiet location, neighbors close by
1 – in-town home, little or no privacy

# of Bedrooms:  5
Bed Sizes: (2) Kings (1) Queen (4) Singles

# of Bathrooms: 2.5
Bathroom Type: (1) Full Bathroom (1) Shower Only (1) Half Bath

Smoking AND/OR Fireworks Are Prohibited on EVERY Property

Cottage Connection of Maine represents a wide variety of quality vacation rentals throughout the Mid Coast Region of Maine. Individually and privately owned, each vacation rental reflects the taste of its property owners. Every effort has been made to ensure that the descriptions and amenities listed are accurate. However, occasionally changes are made by the owners to furnishings, amenities and equipment. Once a change that has occurred is brought to our attention, we will update that webpage. If you have any specific questions not addressed above or are in search of specific criteria, please contact us.

In other seasons (Spring or Fall), arrival dates may be flexible, speak to the reservationist.  Also, if you book a 7 night stay in the shoulder season, a 15% discount will be applied to your weekly rate.

Linens are provided for the guests stay (sheets and towels)  /  This is a pet friendly property but under specified conditions, please discuss with reservationist  /  Wood is not supplied by the owner, but may be purchased in many places along Route 27, coming into town, our local campgrounds (Shore Hills and Grays Homestead) as well as the local grocery store Hannaford's.

Mooring available for up to a 20' boat with motor, with payment of a mooring fee.  Ask your reservationist for details.

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