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Southport Rentals

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145 Results

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145 Houses

Waterfront Estate on Pratt's Island w/ Bunk House & Loft - Near Dining

Southport house

6 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$838

Southport Island Cottage | Deck & New Luxe Kitchen | Near Boothbay Harbor

Southport cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$164

On the Water Southport Island with Breathtaking Views - Sprucerock Cabin

Southport log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$263

Little Nick - A Sweet Little Haven with a Peak of the Ocean

Southport guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$133

Periwinkle Cottage - A Cozy Retreat on Southport Island, Maine

Southport cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$175

Seawood Rural Island Retreat | Chef’s Kitchen, Loft & Yard | 5 Mins to Water

Southport house

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$231

Capitol Island Retreat | Exceptional Oceanfront Views | Marina & Beach

Southport cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$315

Waterfront Gem at Capitol Island with Screened Porch, Balcony & Clubhouse

Southport apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$371

3500 Square-Foot Bayfront Getaway | Scenic Multi-Level Deck & Private Dock

Southport house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$458

Waterfront Delight | Guesthouse | Amazing Sunset Views & Private River Access

Southport house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$357

Waterfront Retreat & Guest House | Private Dock, Kayaks | Lovely Cove Views

Southport house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$779

Great rentals within 20 miles that match your search

Charming oceanfront cottage

Cape Neddick cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$365

Maine Island Lodge

Friendship lodge

7 bedrooms / 6 bathrooms / sleeps 18

Price per night from

$1,309

Private Island - Great for Reunions - Sleeps 24

Port Clyde house

11 bedrooms / 6 bathrooms / sleeps 24

Price per night from

$2,803

Ocean Front Cottage, Harpswell, ME

Harpswell cottage

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$280

Light Filled, Woodsy Views, Atlantic Ocean Nearby - Classic Mid-Coast Cottage

New Harbor cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$190

OceanView BonnieView

Round Pond house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$210

Beautiful waterfront home

Boothbay Harbor condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$167

Ocean Point, Maine Cottage Weekly Rental

East Boothbay cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$332

Waterfront Private Estate w dock on 6 acres

Cundys Harbor house

5 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 45 minutes

Price per night from

$900

Port Cabin - New Inground Pool overlooking the Ocean on Beautiful Linekin Bay

Boothbay Harbor house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$572

Gathering Point Cottage, Water View, Walk to Aquarium, Beach Access

Boothbay Harbor house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$307

Lobster Haven

Boothbay Harbor house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$309

Maine Village Properties

Wiscasset house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$345

Beautiful Boothbay Vacation home

Boothbay Harbor house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$311

The Loft Guest Cottage

New Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$196

Historic Captain York House: 7 Bed, 6.5 Bath

Bailey Island house

7 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$571

Oar Island

Bremen cottage

3 bedrooms / 1 bathroom / sleeps 8

“perfect” We love Oar Island. It is the perfect vacation place for families with children of different ages, or just a couple. There is hiking, sunning, relaxation, but mostly what we love about Oar Island is the isolation. It is an adventure as well, since the only way to get there is by the little motorboat. It is a getaway for certain kinds of people; but if you prefer the Marriott type of stay, this is not that kind, it is much more "out-doorsy".

Responds fast! avg. 2 hours 5 minutes

Price per night from

$243

Remarkable Four Gable House Overlooking Friendship Harbor

Friendship house

8 bedrooms / 6 bathrooms / sleeps 18

Responds fast! avg. 3 hours 46 minutes

Price per night from

$394

Brand New Modern Loft Home

Topsham house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 54 minutes

Price per night from

$135

South Bristol Boathouse

South Bristol house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$281

Trick's End - A Beautiful Get Away on the Coast of Barter's Island

Trevett house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$360

Waterfront Cottage, Stroll Away from Historic Bath

Bath cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 22 minutes

Price per night from

$275

Bluewater Vista - Ocean Views, Dock Access, Tennis, Boothbay Harbor

Bayville cottage

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$299

The Hilltop Boothbay Harbor Steps from the Footbridge and in town dog friendly

Boothbay Harbor house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$276

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