We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Southport Island, ME

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
Payment
Select
Go to map view
More filters
All 15 Rentals in Southport Island
loading...
Sort by
From
₹33,374
/ Night
View Details
1 / 31
5 of 5 stars (1) Excellent
Southport
3 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (1) Make Enquiry
From
₹28,615
/ Night
View Details
1 / 19
Southport
3 Bedrooms / 2 Bathrooms / Sleeps 5
Overview Make Enquiry
From
₹57,103
/ Week
Payment Protection
View Details
1 / 12
Southport
2 Bedrooms / 1 Bathroom / Sleeps 4
Overview Make Enquiry
From
₹28,996
/ Night
Payment Protection
View Details
1 / 22
Southport
6 Bedrooms / 6 Bathrooms / Sleeps 12
Overview Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Coveside House, a Sea Captain-style home overlooking Decker's Cove,is located on beautiful Southport Island on the coast of Maine, just an hour's drive from Portland, and minutes from Boothbay Harbor. This coastal home is approximately 140 years old having gone through several transformations and... View all property information
Make Enquiry
From
₹24,935
/ Night
View Details
1 / 18
Southport
2 Bedrooms / 2 Bathrooms / Sleeps 4
Overview Make Enquiry
Amenities & Details
  • Fireplace
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
A dream that has been repeating but now seems to be coming true has often been used to characterize past guests experiences after staying at Barnacles. What one will often describe when asked what they envision their Maine vacation on the rocky coast of Maine would look like. This classic Maine... View all property information
Make Enquiry
From
₹26,712
/ Night
View Details
1 / 24
Southport
3 Bedrooms / 2 Bathrooms / Sleeps 5
Overview Make Enquiry
Amenities & Details
  • Dishwasher
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Spectacular Ocean Views from almost every room of this Island Cottage! Ocean, islands, boats of all kinds and a sandy beach, make it the perfect spot for a Maine Oceanfront Vacation. Enjoy your meals outside on the terrace area – gas grill, dining set, outside patio furniture and more to make... View all property information
Make Enquiry
From
₹27,727
/ Night
View Details
1 / 35
Southport
5 Bedrooms / 3 Bathrooms / Sleeps 10
Overview Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
PIFFI BIFF 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... View all property information
Make Enquiry
From
₹25,252
/ Night
View Details
1 / 28
Southport
2 Bedrooms / 2 Bathrooms / Sleeps 4
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
PINE CLIFF DWELLER Pine Cliff Dweller is perched on the edge of a cliff overlooking Burnt and Squirrel Islands and the entrance to Boothbay Harbor and the open Atlantic! The owners of this magnificent property have maximized the view with tons of windows, covered and uncovered decks and indoor... View all property information
Make Enquiry
From
₹28,044
/ Night
View Details
1 / 31
Southport
3 Bedrooms / 3 Bathrooms / Sleeps 5
Overview Make Enquiry
Amenities & Details
  • Fireplace
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Crashing ocean at your feet! This wonderful classic Maine summer cottage sits up high right on the Atlantic Ocean. Island Retreat is located on the east side of Southport Island. Enjoy island and boating views! There is a shared beach nearby for swimming. Lots of space in this three bedroom cottage... View all property information
Make Enquiry
From
₹29,313
/ Night
View Details
1 / 35
Southport
4 Bedrooms / 2 Bathrooms / Sleeps 7
Overview Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
TIDEWATER FARM This is Island Living the way we do it in Maine! Tidewater Farm is a beautiful little cottage located on Southport Island, about three miles from Boothbay Harbor. Once you come across the swing bridge, notice the second hand on your watch slow right down. Stunning views, cove and... View all property information
Make Enquiry
Get the List
From
₹76,137
/ Week
View Details
1 / 24
3 Bedrooms / 1 Bathroom / Sleeps 6
Overview Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Noteworthy is the land and dock immediately to the right of the cottage as you look at the water. This dock is the private association dock for the neighborhood, but only a few neighbors actually use it. So, this property not only has access to its dock immediately in front of it, but also the... View all property information
Make Enquiry
From
₹23,476
/ Night
View Details
1 / 17
Southport
3 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
MOLLY’S CAPE Molly’s Cape is perfect for an active family wanting to swim and kayak as well as anyone looking for a quiet, beautiful place to soak up the sunshine and listen to the ocean! Located on the west side of Southport Island Molly’s Cape provides the perfect out-of-the-way location with... View all property information
Make Enquiry
From
₹95,172
/ Week
View Details
1 / 35
5 Bedrooms / 3 Bathrooms / Sleeps 12
Overview Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The property is located on a quiet narrow road so although the road separates the cottage and barn, even the youngest of children can safely walk across the road between the two. The bathrooms in the main cottage were renovated in 2014. Air conditioning was also added to the main home. Enjoy the... View all property information
Make Enquiry
From
₹76,137
/ Week
View Details
1 / 34
4 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Robinson's Wharf - which has the Restaurant & Tug Pub, a Gift Shop, and Seafood Market, as well as an ice cream stand, is within a short walking distance from this property. View all property information
Make Enquiry
Inquire for rates
1 / 16
Southport
4 Bedrooms / 2 Bathrooms / Sleeps 7
Overview Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Early 1800's Maine home on Cosy Harbor with a shared dock and float. You are welcome to share our 2 kayaks when available. The dock is tidal, but has water around it most of the tide(8'at high tide). Walk to the Southport Yacht Club, Beaches, or the General Store for ice cream. The yacht club... View all property information
Make Enquiry