Holiday Houses in Southport

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185 Holiday homes

Oceanfront contemporary home with stunning island and lighthouse views

Newagen house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 32 minutes

from £193 / night

£1,351 / week

Charming, Single-Level Summer Cottage on Southport Island

Newagen house

3 bedrooms / 2 bathrooms / sleeps 4

from £354 / night

£2,478 / week

Bold Oceanfront Cottage on Southport Island

Southport house

3 bedrooms / 2 bathrooms / sleeps 6

from £375 / night

£2,622 / week

Cozy_Cottage_Southport_Island

Southport house

3 bedrooms / 2 bathrooms / sleeps 6

from £150 / night

£1,045 - £1,829 / week

OCEAN WAY ON SOUTHPORT ISLAND | QUIET WOODLAND RETREAT NEAR BEACH

Southport house

2 bedrooms / 1 bathroom / sleeps 4

from £127 / night

£889 / week

Sprucerock_Southport_Island

Newagen house

3 bedrooms / 2 bathrooms / sleeps 6

from £219 / night

£1,532 / week

Mollys_Cape_Southport

Southport house

3 bedrooms / 2 bathrooms / sleeps 6

from £277 / night

£1,935 / week

Two Bedroom, Classic Summer Cottage on Southport Island

Southport house

2 bedrooms / 2 bathrooms / sleeps 4

from £257 / night

£1,799 / week

Classic Maine Cottage on Southport Island

Southport house

5 bedrooms / 3 bathrooms / sleeps 10

from £293 / night

£2,046 / week

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

Southport guest house

1 bedroom / 1 bathroom / sleeps 2

from £95 / night

£796 / week

Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen

Southport cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 32 minutes

from £130 / night

£905 / week

NEW LISTING! Stunning oceanfront cottage w/ private deck and ocean views!

Newagen house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 32 minutes

from £103 / night

£719 / week

Periwinkle Cottage - A Cozy Retreat on Southport Island, Maine

Southport cottage

2 bedrooms / 1 bathroom / sleeps 4

from £136 / night

£1,054 / week

Great rentals within 20 miles that match your search

Laughton House & Cottages - Cabin - Low Tide

New Harbor cottage

1 bedroom / 1 bathroom / sleeps 3

27

Responds fast! avg. 18 minutes

from £102 / night

£662 - £724 / week

Ocean-view Colonial 6 Bedroom Home on Spruce Point

Boothbay Harbor house

7 bedrooms / 4 bathrooms / sleeps 11

from £551 / night

£3,851 / week

from £222 / night

£713 / week

Beautiful waterfront home

Boothbay Harbor condo

2 bedrooms / 2 bathrooms / sleeps 4

from £120 / night

£839 - £1,280 / week

Oceanfront Cottage on Southport Island with Private Dock and Float

East Boothbay house

2 bedrooms / 2 bathrooms / sleeps 4

from £256 / night

£1,792 / week

Pet Friendly, Waterfront Cottage on Spruce Point

Boothbay Harbor house

4 bedrooms / 2 bathrooms / sleeps 7

1

from £243 / night

£1,700 / week

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

Bayville cottage

4 bedrooms / 3 bathrooms / sleeps 8

from £240 / night

£1,678 / week

Spectacular Ocean Views & Private Beach, Minutes from Popham & Sebasco Resort

Phippsburg house

3 bedrooms / 3 bathrooms / sleeps 8

5

from £174 / night

£1,218 / week

Finch Cottage

New Harbor house

2 bedrooms / 2 bathrooms / sleeps 4

7

from £111 / night

£773 / week

Oceanfront Cottage with private beach-Pet friendly

West Bath house

3 bedrooms / 2 bathrooms / sleeps 8

2

from £152 / night

£1,060 - £2,296 / week

A Writer's Home at the Edge of the Forest on the Boothbay Peninsula

Boothbay house

2 bedrooms / 2 bathrooms / sleeps 5

from £115 / night

£804 / week

Spruce_Point_Landing_Boothbay_Harbor

Boothbay Harbor house

5 bedrooms / 4 bathrooms / sleeps 10

1

from £669 / night

£4,680 / week

SOUTHPORT waterfront historic farmhouse w dock

Boothbay Harbor house

4 bedrooms / 3 bathrooms / sleeps 5

from £354 / night

£2,472 / week

NEW! Charming East Boothbay Cottage w/ Large Yard!

Bayville cottage

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 35 minutes

from £111 / night

£773 / week

Happy Hippie Lane Maine: Your Groovy Restore and Explore Midcoast Destination

Wiscasset camper van

1 bedroom / 3 bathrooms / sleeps 36

from £58 / night

£367 - £3,518 / week

Pet Friendly, Historic Farmhouse on Sawyer's Island

Boothbay house

4 bedrooms / 2 bathrooms / sleeps 10

3

from £232 / night

£1,621 / week

Pet Friendly Cottage in Boothbay Harbor, Just a Short Walk From Downtown.

Boothbay Harbor house

2 bedrooms / 1 bathroom / sleeps 4

from £148 / night

£1,032 / week

Historic Captain York House: 7 Bed, 6.5 Bath

Bailey Island house

7 bedrooms / 6 bathrooms / sleeps 14

from £438 / night

£3,063 / week

OCEAN FRONT IN THE HEART OF BOOTHBAY HARBOR, PET FRIENDLY

Boothbay Harbor house

3 bedrooms / 2 bathrooms / sleeps 10

from £451 / night

£3,155 / week

Mazu, the Bed&Boat, the most waterfront cottage

Damariscotta yacht

2 bedrooms / 2 bathrooms / sleeps 6

5

from £199 / night

£1,326 - £1,945 / week

Waterfront Private Estate w dock on 6 acres

Cundys Harbor house

5 bedrooms / 4 bathrooms / sleeps 8

from £694 / night

£4,861 / week

MERWICK COTTAGE | GEORGETOWN, MAINE |WATERFRONT | PRIVATE DOCK AND FLOAT

Georgetown house

3 bedrooms / 2 bathrooms / sleeps 6

from £266 / night

£1,062 / week

Discover a Family Tradition on Linekin Bay

Bayville house

6 bedrooms / 3 bathrooms / sleeps 16

from £695 / night

£4,861 / week

Laughton House & Cottages - High Tide Cabin

New Harbor cottage

1 bedroom / 1 bathroom / sleeps 3

5

Responds fast! avg. 18 minutes

from £102 / night

£663 / week

Camp Forever

Harpswell studio

Studio / 1 bathroom / sleeps 3

6

Responds fast! avg. 1 hour 13 minutes

from £155 / night

£663 / week

Fairview_Boothbay

Boothbay house

3 bedrooms / 3 bathrooms / sleeps 6

3

from £240 / night

£1,681 / week

Captains_Quarters_East_Boothbay

East Boothbay house

8 bedrooms / 3 bathrooms / sleeps 16

1

from £728 / night

£5,095 / week

Viewing 40 of 185
rentals in Southport

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