Southport Island, Maine Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Southport Island, Maine on RentalSaver.com!

Southport Island Rentals

From $816 per night (USD)
VRBO
Saltwater farmhouse on 2+ acres of waterfront with private dock
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Hartwell House has origins in the 1770s and expanded in the 1800s and 1970s. It is in a protected cove off Ebenecook Ba ...
From $816 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Snowman Cottage -- Southport Enjoy water views of Cape Harbor and the open ocean from nearly every room in this 3-bedroo ...
From $319 per night (USD)
VRBO
From $95 per night (USD)
VRBO
Boothbay Harbor, Maine Beautiful Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This room has a personal key. Spacious Bedroom with a firm Queen Bed, a love seat, and a comfortable chair, a refrigera ...
From $95 per night (USD)
VRBO
$Two-Story Family-Friendly Home w\/Free WiFi, Deck, and Partial Ocean Views$
From $443 per night (USD)
Expedia
Two-Story Family-Friendly Home w\/Free WiFi, Deck, and Partial Ocean Views
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Cape Newagen Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $443 per night (USD)
Expedia
$Waterfront Cottage with a dock & float on Townsend Gut w\/one floor living$
From $300 per night (USD)
VRBO
Waterfront Cottage with a dock & float on Townsend Gut w\/one floor living
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This charming 2 bedroom, 1 bath cottage sits right at the water's edge of Townsend Gut. Boats galore can be seen from th ...
From $300 per night (USD)
VRBO
From $164 per night (USD)
VRBO
Charming Plumpoint Cottage On Southport Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the serenity of beautiful Southport Island in a classic Maine cottage with a peek at Decker's Cove. Walk to Robins ...
From $164 per night (USD)
VRBO
From $988 per night (USD)
VRBO
The ultimate vacation spot, 4 BR waterfront cottage overlooking the open ocean
Bedrooms:
2
Bathrooms:
5
Sleeps:
13
The ultimate Maine vacation spot! Enjoy the open ocean and boating activity from this 4 bedroom, 2 bath waterfront cotta ...
From $988 per night (USD)
VRBO
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Expedia
3 Bedroom Classic Maine Cottage, Close To Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Open floor plan cottage, on wooded, private lot, less than 5 minute walk to beautiful, perfect-for-kids beach. Well equ ...
Click For Pricing
Expedia
$Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A\/C$
From $289 per night (USD)
VRBO
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A\/C
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Come enjoy the peaceful tranquility of this lakefront retreat just 5 minutes from the quaint seaside shops and restauran ...
From $289 per night (USD)
VRBO
$Stunning oceanfront cottage w\/ private deck and Atlantic views$
From $453 per night (USD)
Expedia
Stunning oceanfront cottage w\/ private deck and Atlantic views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Serene Newagen House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $453 per night (USD)
Expedia
From $323 per night (USD)
VRBO
Charming cottage overlooking picturesque Five Islands Harbor
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
3 Bedroom cottage overlooking the quintessential Maine working harbor of Five Islands. Watch lobster boats come and go ...
From $323 per night (USD)
VRBO
From $178 per night (USD)
VRBO
Waterfront Cottage With An Awesome View Of Capital And Burnt Island
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Two story home, with 3 bedrooms upstairs and Bathroom down stairs.Large living area with a beautiful view of the ocean a ...
From $178 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Fun, unique spot with lots of diverse boats traveling right by property. Seasonal cottage with great views, private doc ...
From $382 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Steamboat Landing Cottage
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Steamboat Landing is a large cottage overlooking the Sheepscot River on Southport Island. Hosted by Of Sea and Pine; Mai ...
From $442 per night (USD)
Expedia
From $232 per night (USD)
VRBO
A Cozy Retreat on Southport Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cute-as-a-button newly renovated waterfront cottage is located on Southport Island across the swing bridge from Boo ...
From $232 per night (USD)
VRBO
From $376 per night (USD)
Expedia
A Picturesque Cottage on Capitol Island, Maine
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Capitol Island is the epitome of quintessential Maine! Capitol with a Sea cottage is situated just above the docks at t ...
From $376 per night (USD)
Expedia
From $505 per night (USD)
VRBO
Newly Restored 1920's Vintage Boathouse.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Impeccably restored former boathouse. Very unique property that features a spectacular view of Boothbay Harbor and the o ...
From $505 per night (USD)
VRBO
From $690 per night (USD)
VRBO
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
On the water with expansive views and a private deepwater dock on the property for your boat. This location cannot be be ...
From $690 per night (USD)
VRBO
From $654 per night (USD)
VRBO
Oceanfront Log Cabin with Dock on Southport Island - 7 acres with westerly views
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Log cabin on Love's Cove and looking west over Ebenecook Bay on Southport Island. Built and furnished in 1909 by the sa ...
From $654 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Historical New England home with outdoor shower - near downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Firehouse Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $306 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Southport Island Cottage | Deck & New Luxe Kitchen | Near Boothbay Harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Southport Island Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $314 per night (USD)
VRBO
From $568 per night (USD)
Expedia
Beachfront Delight with detached guesthouse, sunset views & private beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Deep Cove Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $568 per night (USD)
Expedia
From $612 per night (USD)
VRBO
Decker Cove Southport Paradise with Central Air Conditioning
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Brand new construction in 2019. 3 bed, 3 bath home. Partial view of Decker Cove from all bedrooms, walking distance to R ...
From $612 per night (USD)
VRBO
From $323 per night (USD)
VRBO
Relax over looking the quaint Five Islands Harbor in Georgetown Maine
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This 3 bedroom cottage sits right on the picturesque harbor of Five Islands with views out to the Sheepscot River and be ...
From $323 per night (USD)
VRBO
$Secluded Dog-Friendly Getaway w\/ Free WiFi, Private Washer\/Dryer, Furnished Deck$
From $342 per night (USD)
VRBO
Secluded Dog-Friendly Getaway w\/ Free WiFi, Private Washer\/Dryer, Furnished Deck
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Island Pines Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $342 per night (USD)
VRBO
From $311 per night (USD)
VRBO
Updated Cottage on Water’s Edge with Deepwater Boat Dock!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
On the water with deepwater dock for your boat - this location cannot be beat. This cottage is located on Southport Isla ...
From $311 per night (USD)
VRBO
$3 one-bedroom fully equipped cottages with free WIFI \/weekly rental$
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VRBO
3 one-bedroom fully equipped cottages with free WIFI \/weekly rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Dockside Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + ...
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VRBO
$3 one-bedroom fully equipped cottages with free WIFI \/weekly rental$
Click For Pricing
Expedia
3 one-bedroom fully equipped cottages with free WIFI \/weekly rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Tan Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + resta ...
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Expedia
$3 one-bedroom fully equipped cottages with free WIFI \/weekly rental$
Click For Pricing
VRBO
3 one-bedroom fully equipped cottages with free WIFI \/weekly rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The White Cottage is located on Decker's Cove overlooking a busy waterway with lots of boat traffic. Lobster wharf + res ...
Click For Pricing
VRBO
$Remodeled Cottage with AC, Private W\/D, Full Kitchen, and High-Speed WiFi$
From $201 per night (USD)
Expedia
Remodeled Cottage with AC, Private W\/D, Full Kitchen, and High-Speed WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Little Cottage in the Woods Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $201 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Waterfront Cottage Sitting On The Water's Edge Of Townsend Gut
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 2 bedroom, 2 bath cottage sits waterfront on Townsend Gut. Sit out on the wrap-around porch and enjoy the abundant ...
From $378 per night (USD)
VRBO
From $352 per night (USD)
Expedia
Charming coastal cottage with high-speed WiFi, furnished deck, gas grill, & dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Blue Shutters Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $352 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Oceanfront home
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Beautiful oceanfront home with large outdoor deck facing the water for dining and relaxing, Great sunsets. Private sand ...
From $547 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
"Harborview Perch": comfortable & inviting with spectacular, elevated views of Boothbay Harbor! "Harborview Perch" a ...
From $326 per night (USD)
Expedia
From $490 per night (USD)
VRBO
Waterfront cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautiful Cottage on Southport Island with access to dock and kayaks. Cozy, the perfect getaway. Gorgeous sunsets. Priv ...
From $490 per night (USD)
VRBO
From $200 per night (USD)
VRBO
Brand new in 2020 Cozy Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our cottage is brand new, built in 2020, Radiant Heat on both 1st and 2nd floor. Enjoy the tranquility of a cozy cottage ...
From $200 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Breathtaking Water Views on Southport Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The sound of the waves will greet you even before you can lay eyes on the ocean. It will call you to the front porch wh ...
From $464 per night (USD)
VRBO
$Oceanfront Cottage w\/ Deck 2 Mi to Boothbay Harbor$
From $494 per night (USD)
Expedia
Oceanfront Cottage w\/ Deck 2 Mi to Boothbay Harbor
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
The moment you arrive at this bright 4-bedroom, 2-bathroom cottage you are sure to be enchanted by its historic New Engl ...
From $494 per night (USD)
Expedia
From $438 per night (USD)
VRBO
Classic Maine Cottage with Ocean Views and Beach
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Stuart Little is a wonderful place to slow down and just breathe. It's a perfect place for making summer memories. The b ...
From $438 per night (USD)
VRBO
From $105 per night (USD)
VRBO
Boothbay Harbor Maine, Beautiful private Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Spacious Living room / kitchenet , comfy couch, Queen Ann chair, bar style table with stools seating. Refrigerator, micr ...
From $105 per night (USD)
VRBO
From $384 per night (USD)
VRBO
Pratts Island Get Away
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Enjoy an island living getaway with this three bedroom two two-bathroom home located across a wooden bridge from Southpo ...
From $384 per night (USD)
VRBO
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Expedia
Spectacular Ocean Front Estate on Southport
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Prepare to be captivated by this extraordinary oceanfront retreat, boasting breathtaking panoramic views of the open oce ...
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Expedia
From $752 per night (USD)
VRBO
Charming Waterfront Cottage with Private Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Established in 1844 and rich with history and charm, The Boathouse is the perfect little getaway spot for couples and fa ...
From $752 per night (USD)
VRBO
From $1214 per night (USD)
Expedia
Stunning Ocean Front Estate with a Private Dock
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Relax and unwind in this spacious and peaceful oceanfront setting just minutes from fine dining, hiking trails, shopping ...
From $1214 per night (USD)
Expedia
From $147 per night (USD)
VRBO
A Sweet Little Guest Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Tucked away on Southport Island is this little guest house for two. Located just across the swing bridge from Boothbay H ...
From $147 per night (USD)
VRBO
From $316 per night (USD)
VRBO
3 BR, 1.5 BA home is perfect for your visit to Boothbay Harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This spacious, comfortable one-level, 3 bedroom, 1 1/2 bath home has a large yard, views of the Sheepscot River and Indi ...
From $316 per night (USD)
VRBO
From $490 per night (USD)
VRBO
Boothbay area -- Newly renovated, near ocean, short drive to Botanical Gardens
Bedrooms:
4
Bathrooms:
4
Sleeps:
13
Welcome to this modern architectural gem tucked among the spruces on Southport Island, serenely peaceful and yet just a ...
From $490 per night (USD)
VRBO
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Expedia
Charming Southport Island Cottage on Cozy Harbor with Sunny Deck - Sleeps 6!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Enjoy the spectacular natural beauty of Cozy Harbor and delight in watching all the harbor activity from the privacy of ...
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Expedia
From $628 per night (USD)
VRBO
Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Let it all go! Come here for peace and respite. Welcome to quintessential Maine summer living! Enjoy stunning ocean v ...
From $628 per night (USD)
VRBO
From $634 per night (USD)
Expedia
PINE CLIFF DWELLER | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. STAY ...
From $634 per night (USD)
Expedia
From $1087 per night (USD)
VRBO
LEDGEMERE ON SOUTHPORT ISLAND | 3 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER _________________________________________________________ ...
From $1087 per night (USD)
VRBO
From $669 per night (USD)
Expedia
PIFFI BIFF ON SOUTHPORT ISLAND | 5 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. STAY THE ...
From $669 per night (USD)
Expedia
Click For Pricing
VRBO
Coastal Cottage - Panoramic Views - Pond & Nature
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our family's favorite Maine coastal cottage! Although small in size, 600 SF - Gull Cottage is overflowing w ...
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VRBO
From $1339 per night (USD)
Expedia
A SLICE OF HEAVEN | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
THIS PROPERTY RENTS WEEKLY, FRIDAY - FRIDAY, JUNE, JULY, AND SEPTEMBER ONLY ___________________________________________ ...
From $1339 per night (USD)
Expedia
From $1126 per night (USD)
VRBO
Ocean front cottage on a drive-on island in Boothbay Harbor, Maine
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Exquisitely maintained 5 bedroom/2 bathroom cottage right on the ocean. Family owned since 1891. Step back in time into ...
From $1126 per night (USD)
VRBO
From $405 per night (USD)
VRBO
Cedar Cove: a tranquil retreat on the water just minutes from Boothbay Harbor
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Cedar Cove was completed in 2023 and designed for tranquility: find yourself surrounded by woods and water, in a beauti ...
From $405 per night (USD)
VRBO
$Generational Southport Property w\/ Private Beach Newly Available for Rent!$
Click For Pricing
VRBO
Generational Southport Property w\/ Private Beach Newly Available for Rent!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
**CONTACT US TO SEE RENTING AVAILABILITY** Get ready to enjoy amazing afternoon sun on your own private sandy beach, lo ...
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VRBO
From $615 per night (USD)
Expedia
MERWICK COTTAGE | GEORGETOWN | 3 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. WEEKLY SP ...
From $615 per night (USD)
Expedia
From $614 per night (USD)
VRBO
NEW FOR 2024 | SEA MIST | 4 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
THIS HOME RENTS WITH A 7-NIGHT MINIMUM, JUNE-LABOR DAY 4-NIGHT MINIMUM IN FALL. STAY THE WEEK FOR A SPECIAL RATE! ____ ...
From $614 per night (USD)
VRBO
From $1111 per night (USD)
Expedia
CLIFF COTTAGE | TOWNSEND GUT | 4 Bed, 2.5 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
THIS PROPERTY RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. Welco ...
From $1111 per night (USD)
Expedia
From $657 per night (USD)
VRBO
THE LEDGE ON SOUTHPORT ISLAND | 3 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
THIS PROPERTY RENTS SATURDAY - SATURDAY, TWO WEEKS MINIMUM _____________________________________________________________ ...
From $657 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Seawood Sunset Cottage: Southport Island
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Seawood Sunset Cottage is located on the beautiful island of Southport. Built by an artist and displaying much of her wo ...
From $328 per night (USD)
Expedia
From $910 per night (USD)
VRBO
Waterfront Home on Decker Cove
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sit out on the covered porch or open deck and enjoy the boating activity out on Townsend Gut and across the protected co ...
From $910 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Cozy Ocean Side Cottage with screened in Sun room! 5 minutes from Private beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
TheCottageAtFiveIslands.com The Cottage is a fully furnished 900 sq ft two bedroom with full kitchen, bathroom and livi ...
From $344 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Cottage at Island Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come enjoy coastal Maine island living at this comfortable Southport cottage. This peaceful Newagen retreat will make y ...
From $368 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Cozy Waterfront Cottage with Dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step into the charm of coastal Maine at The Lilly Pad, a lovingly restored 1940s cottage nestled on the tranquil shores ...
From $299 per night (USD)
Expedia
From $972 per night (USD)
VRBO
Miradon Ocean Estate
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Miradon Ocean Estate affectionately known as “Ole Gusty”, is an extraordinary oceanfront retreat. Designed to showcase p ...
From $972 per night (USD)
VRBO

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Southport Island Rentals

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Results: 67 Rentals