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Southport Rentals

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141 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

$728

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

$261

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

$132

Periwinkle Cottage - A Cozy Retreat on Southport Island, Maine

Southport cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$174

2BR 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

New Listing! 3500 Sq. Ft. Bayfront Getaway w/ Incredible Views & Private Dock

Southport house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$458

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

$360

Maine Island Lodge

Friendship lodge

7 bedrooms / 6 bathrooms / sleeps 18

Price per night from

$1,290

Open Ocean Estate w/ path to neighborhood beach

Bailey Island house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,103

Private Island - Great for Reunions - Sleeps 24

Port Clyde house

11 bedrooms / 6 bathrooms / sleeps 24

Price per night from

$2,763

Meadow View Artist Retreat

Monhegan Island apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$258

Ocean Front Cottage, Harpswell, ME

Harpswell cottage

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$276

Oceanfront Cottage on Middle Bay

Harpswell house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$348

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

New Harbor cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$188

The Barn

Alna house

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$360

OceanView BonnieView

Round Pond house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$207

Beautiful waterfront home

Boothbay Harbor condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$165

Waterfront Home on Scenic Cove

Harpswell house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$181

Ocean Point, Maine Cottage Weekly Rental

East Boothbay cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$327

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

$357

Ocean Waterfront - Walk to Pemaquid Light

New Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$362

Maine Cottage, Mid-Coast Maine

South Bristol cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 37 minutes

Price per night from

$158

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

$887

The Loft Guest Cottage

New Harbor house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$194

Spacious Deck, Shared Dock, Linekin Bay Cottage & Apartment

Boothbay Harbor cottage

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$344

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

$564

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

Boothbay Harbor house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$302

Beachfront Cottage on Indian Point

Georgetown cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$314

Scenic White Rocks Cottage on the Maine Coast

Georgetown cottage

2 bedrooms / 1 bathroom / sleeps 6

“Beautiful setting on Kennebeck River” Husband and I stayed short of a week, enjoyed the screened porch watching the activity on the Kennecbeck, especially the tour boat loaded with fellow vacationers.Cottage was very pleasant and had everything we needed. But we did find the upstairs stairs a little hard for us to maneuver being rather steep and narrow, so we utilized the sleeper sofa that was very comfortable located downstairs all in all we managed fine and enjoyed our time ar White Rocks, owner lives within view of cottage at end of road we frequented the Georgetown store for their huge dinner plate size blueberry pancakes which my husband enjoyed frequently.

Price per night from

$140

Classic Maine Cottage with Ocean Views and Beach

Boothbay Harbor cottage

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$325

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".

Price per night from

$244

A Regal House in Downtown Boothbay Harbor - The Red House

Boothbay Harbor house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$285

Brand New Modern Loft Home

Topsham house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 54 minutes

Price per night from

$137

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