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 $841 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 $841 per night (USD)
VRBO
From $315 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 $315 per night (USD)
VRBO
From $97 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 $97 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
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VRBO
Pennoyer Point Cottage - 4 BR Waterfront Cottage B- Mooring Access + Shared Dock
Bedrooms:
1
Bathrooms:
4
Sleeps:
13
Ultimate Classic Maine Waterfront Cottage – Perfect for Family Fun! Welcome to the ultimate Maine vacation spot, where ...
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VRBO
From $164 per night (USD)
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 ...
From $164 per night (USD)
Expedia
From $275 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 $275 per night (USD)
VRBO
From $287 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 $287 per night (USD)
Expedia
From $189 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 $189 per night (USD)
VRBO
From $536 per night (USD)
Expedia
Steamboat Landing Cottage: Water Views, Nearby Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Steamboat Landing - Southport Island, Maine. Nestled between Sheepscot Bay and Boothbay, Southport Island is connected ...
From $536 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Periwinkle by Sea Maine
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This cute-as-a-button waterfront cottage is located on Southport Island across the swing bridge from Boothbay Harbor. "P ...
From $378 per night (USD)
VRBO
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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 ...
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Expedia
From $907 per night (USD)
VRBO
Newly Restored 1920's Vintage Boathouse.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Impeccably restored former boathouse. Very unique property that features a spectacular view of Boothbay Harbor and the o ...
From $907 per night (USD)
VRBO
From $690 per night (USD)
VRBO
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!
Bedrooms:
2
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 $266 per night (USD)
VRBO
Historical New England home, outdoor shower , Dog-friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Firehouse Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $266 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Romley House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $254 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Beachfront Delight with detached guesthouse, private beach access, Dog-friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Deep Cove Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $487 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Decker Cove Southport Paradise with Central Air Conditioning
Bedrooms:
3
Bathrooms:
3
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 $541 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Island Pines Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $353 per night (USD)
VRBO
From $272 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 $272 per night (USD)
VRBO
From $174 per night (USD)
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 + ...
From $174 per night (USD)
VRBO
From $174 per night (USD)
Expedia
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 ...
From $174 per night (USD)
Expedia
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VRBO
Remodeled Cottage with AC, Private W/D, Full Kitchen, and High-Speed WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Little Cottage in the Woods Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
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VRBO
From $453 per night (USD)
Expedia
Water's Edge - Waterfront Cottage on Southport - Wrap-Around Porch!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Charming Waterfront Cottage with Stunning Views of Townsend Gut - Southport! Nestled right on the waterfront of Townse ...
From $453 per night (USD)
Expedia
From $267 per night (USD)
VRBO
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 $267 per night (USD)
VRBO
From $547 per night (USD)
VRBO
Oceanfront home
Bedrooms:
1
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 $316 per night (USD)
VRBO
Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
"Harborview Perch": comfortable & inviting with spectacular, elevated views of Boothbay Harbor! "Harborview Perch" a ...
From $316 per night (USD)
VRBO
From $432 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 $432 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Decker Cove Cottage, new in 2020!
Bedrooms:
1
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 $305 per night (USD)
VRBO
From $747 per night (USD)
Expedia
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 $747 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
Bedrooms:
2
Bathrooms:
4
Sleeps:
4
The moment you arrive at this bright 4-bedroom, 2-bathroom cottage you are sure to be enchanted by its historic New Engl ...
From $486 per night (USD)
VRBO
From $118 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 $118 per night (USD)
VRBO
From $182 per night (USD)
VRBO
Boothbay Open Plan 1- Bedroom Apt. Woods & Water. Southport.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located on Southport Island, we are near the water, and adjacent to Capitol Island. This detached garage apartment is sp ...
From $182 per night (USD)
VRBO
From $381 per night (USD)
VRBO
Southport ME Waterfront - Cozy Harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Enjoy an island getaway on a private island off Southport, ME yet only 10 minutes to Boothbay Harbor. The house sits on ...
From $381 per night (USD)
VRBO
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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 ...
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VRBO
From $921 per night (USD)
Expedia
Stunning Ocean Front Estate with a Private Dock
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Relax and unwind in this spacious and peaceful oceanfront setting just minutes from fine dining, hiking trails, shopping ...
From $921 per night (USD)
Expedia
From $141 per night (USD)
VRBO
A Sweet Little Guest Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tucked away on Southport Island is this little guest house for two. Located just across the swing bridge from Boothbay H ...
From $141 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Samoset Cottage - 3 BR Water View Home, Boothbay Harbor
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Riverside Retreat – Spacious, Peaceful Home with Water Views & Private Dock! Settle into comfort and tranquility at thi ...
From $410 per night (USD)
Expedia
From $665 per night (USD)
VRBO
Boothbay area -- Newly renovated, near ocean, short drive to Botanical Gardens
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
Only 12 minutes from Coastal Maine Botanical Gardens, home of Gardens Aglow. Welcome to this modern architectural gem tu ...
From $665 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 $631 per night (USD)
VRBO
Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach
Bedrooms:
1
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 $631 per night (USD)
VRBO
From $836 per night (USD)
Expedia
PINE CLIFF DWELLER | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. STAY THE ...
From $836 per night (USD)
Expedia
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VRBO
Unforgettable Oceanfront: Panoramic Ocean Views Await at Ledgemere Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, JUNE - SEPTEMBER _________________________________________________________ ...
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VRBO
From $1144 per night (USD)
Expedia
Piffi Biff: Watch Whales & Lobster Boats from This Classic Oceanfront Gem!
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 $1144 per night (USD)
Expedia
From $1222 per night (USD)
VRBO
A SLICE OF HEAVEN | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
THIS HOME RENTS WEEKLY, FRIDAY - FRIDAY, JUNE, JULY, AND SEPTEMBER ONLY _______________________________________________ ...
From $1222 per night (USD)
VRBO
From $1261 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 $1261 per night (USD)
VRBO
From $413 per night (USD)
VRBO
Cedar Cove: a tranquil retreat on the water just minutes from Boothbay Harbor
Bedrooms:
2
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 $413 per night (USD)
VRBO
From $916 per night (USD)
Expedia
Breathtaking Oceanfront Views, Private Dock & Osprey Nest at Merwick Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THIS HOME RENTS WEEKLY, JUNE - SEPTEMBER 4 NIGHT STAYS AVAILABLE IN THE SHOULDER SEASON. WEEKLY SPECIAL AVAILABLE! ___ ...
From $916 per night (USD)
Expedia
From $881 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 $881 per night (USD)
VRBO
From $1833 per night (USD)
Expedia
CLIFF COTTAGE | TOWNSEND GUT | 4 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
THIS HOME RENTS WEEKLY, SATURDAY - SATURDAY, ALL SEASON Welcome to Cliff Cottage, located on Townsend Gut at the top en ...
From $1833 per night (USD)
Expedia
From $399 per night (USD)
VRBO
Seawood Sunset Cottage: Southport Island
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Seawood Sunset Cottage – Southport Island, Maine. Hosted by Of Sea and Pine, Maine Vacation Rentals Built by an artist ...
From $399 per night (USD)
VRBO
From $367 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 $367 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Cottage at Island Point; Charming Coastal Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Cottage at Island Point – Southport Island, Maine. Hosted by Of Sea and Pine, Maine Vacation Rentals Come experienc ...
From $364 per night (USD)
VRBO
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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 ...
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Expedia
From $1068 per night (USD)
VRBO
Miradon Ocean Estate: Expansive Ocean Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Miradon Ocean Estate affectionately known as “Ole Gusty”, is an extraordinary oceanfront retreat. Designed to showcase p ...
From $1068 per night (USD)
VRBO
From $229 per night (USD)
Expedia
Enjoyable 1-bedroom rustic cottage in Southport.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Get ready to relax in this welcoming 1-bedroom rustic cottage in Southport. This gorgeous retreat features a cozy queen ...
From $229 per night (USD)
Expedia
From $585 per night (USD)
VRBO
JONES COTTAGE - Town of Boothbay Harbor
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
THIS PROPERTY ONLY RENTS ON A SATURDAY TO SATURDAY SCHEDULE - 7 NIGHT MINIMUM REQUIRED ROOM LAYOUT: 1st Floor: Kitchen ...
From $585 per night (USD)
VRBO
From $578 per night (USD)
VRBO
Gracious 4-bedroom house in Southport on Townsend Gut with a private pond.
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
This Southport Island house boasts 4 inviting bedrooms with 2 queen beds, 1 full bed, and 1 twin (convertible to king) i ...
From $578 per night (USD)
VRBO
From $202 per night (USD)
VRBO
Charming Two-Bedroom Ocean-View Cottage in Quiet Southport
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located on Southport Island, this cottage is a dream for travelers looking to enjoy the slower pace of life. Sip your mo ...
From $202 per night (USD)
VRBO
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Expedia
Cedarbush Cabin - Waterfront Cottage - walk to Robinson's Wharf!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Mid-Century Modern Charm on the Waterfront! Discover the charm of coastal Maine at Cedarbush Cabin, a classic mid-centu ...
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Expedia
From $279 per night (USD)
VRBO
Charming 3-bedroom cottage in Southport with water views and close to Boothbay.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a fabulous 3-bedroom cottage in Southport. This welcoming retreat features a queen bed, bunk bed, twin bed, an ...
From $279 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Serene Seaside Getaway
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to The Patch House by Sea Maine, a charming and spacious coastal retreat nestled in the serene area of Boothbay ...
From $385 per night (USD)
Expedia
From $437 per night (USD)
VRBO
Waterfront Retreat on Southport Island - Pet-Friendly, Sleeps 6
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to your coastal escape! This 3-bedroom, 1.5-bath waterfront home is tucked away on Southport Island, a hidden ge ...
From $437 per night (USD)
VRBO

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Southport Island Rentals

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Results: 63 Rentals