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Southport Vacation Rentals

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50 rentals in Southport.
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Historic House Featured in March 2015 House Beautiful Magazine!, vacation rental in Southport

Historic House Featured in March 2015 House Beautiful Magazine!

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, vacation rental in Southport

Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Updated Cottage on Water’s Edge with Deepwater Boat Dock!, vacation rental in Southport

Updated Cottage on Water’s Edge with Deepwater Boat Dock!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen, vacation rental in Southport

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Oceanfront  Cottage Southport 3 BR 2BA, Handicapped Accessible, vacation rental in Southport

Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Decker Cove Southport Paradise with Central Air Conditioning, vacation rental in Southport

Decker Cove Southport Paradise with Central Air Conditioning

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful Lake Waterfront with Swim Dock  &Kayaks! Full Kitchen! Heat & air!, vacation rental in Southport

Peaceful Lake Waterfront with Swim Dock &Kayaks! Full Kitchen! Heat & air!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lobster Cove Lookout, vacation rental in Southport

Lobster Cove Lookout

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor, vacation rental in Southport

Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Boothbay/Ocean Point 1/1 Air conditioned Oceanfront apartment, vacation rental in Southport

Boothbay/Ocean Point 1/1 Air conditioned Oceanfront apartment

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Cottage!  2 Bedroom, 2 Bath  **Walk to Town*  1/2 Mile to the Harbor, vacation rental in Southport

Waterfront Cottage! 2 Bedroom, 2 Bath **Walk to Town* 1/2 Mile to the Harbor

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Boothbay Harbor Waterfront Cottage with private dock, vacation rental in Southport

Beautiful Boothbay Harbor Waterfront Cottage with private dock

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy the stunning views while relaxing on the deck at East Ledge Cottage, vacation rental in Southport

Enjoy the stunning views while relaxing on the deck at East Ledge Cottage

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New rental in Boothbay Harbor, try our 'Authentic 'Log Cabin in Maine, vacation rental in Southport

New rental in Boothbay Harbor, try our 'Authentic 'Log Cabin in Maine

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Classic Maine Waterfront Cottage w/ Deepwater Dock, vacation rental in Southport

Classic Maine Waterfront Cottage w/ Deepwater Dock

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cozy Boothbay Harbor Cottage, vacation rental in Southport

Cozy Boothbay Harbor Cottage

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Oceanfront Cottage On Linekin Bay Boothbay Harbor, vacation rental in Southport

Oceanfront Cottage On Linekin Bay Boothbay Harbor

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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In-town, cottage nestled in the woods, short walk to all harbor activities, vacation rental in Southport

In-town, cottage nestled in the woods, short walk to all harbor activities

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Walking Distance To Shops, Restaurants And  Footbridge, vacation rental in Southport

Walking Distance To Shops, Restaurants And Footbridge

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Cedar Log Cabin in Boothbay Harbor, Maine, vacation rental in Southport

Cedar Log Cabin in Boothbay Harbor, Maine

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Enjoy the beautiful scenery., vacation rental in Southport

Enjoy the beautiful scenery.

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quiet family and pet friendly home, vacation rental in Southport

Quiet family and pet friendly home

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming water view home overlooking Mill Cove w/ a large deck - near town, vacation rental in Southport

Charming water view home overlooking Mill Cove w/ a large deck - near town

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lovely waterfront home, harbour-side setting, vacation rental in Southport

Lovely waterfront home, harbour-side setting

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Dog-friendly, bayfront home w/ gorgeous ocean views & a full kitchen, vacation rental in Southport

Dog-friendly, bayfront home w/ gorgeous ocean views & a full kitchen

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Landings East...Classic Waterfront Coastal Home, vacation rental in Southport

Landings East...Classic Waterfront Coastal Home

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lakeside 3 BR Cabin in Boothbay Harbor, vacation rental in Southport

Lakeside 3 BR Cabin in Boothbay Harbor

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Inviting & rustic cabin w/wood-burning fireplace & grill- Enjoy a private beach!, vacation rental in Southport

Inviting & rustic cabin w/wood-burning fireplace & grill- Enjoy a private beach!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Century-old oceanfront home w/ wrap-around porch - walk downtown, dogs OK!, vacation rental in Southport

Century-old oceanfront home w/ wrap-around porch - walk downtown, dogs OK!

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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New listing! Beautiful, dog-friendly home w/ water views, deck, & gas fireplace, vacation rental in Southport

New listing! Beautiful, dog-friendly home w/ water views, deck, & gas fireplace

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Rustic bayfront cottage with fantastic views - just minutes to downtown!, vacation rental in Southport

Rustic bayfront cottage with fantastic views - just minutes to downtown!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Look Out Over the Water from a Cottage in the Water, vacation rental in Southport

Look Out Over the Water from a Cottage in the Water

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Coastal Island Retreat -   Privacy and Convenience. Boat rental available., vacation rental in Southport

Coastal Island Retreat - Privacy and Convenience. Boat rental available.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pointed Fir Cove - Ocean Manor Home, vacation rental in Southport

Pointed Fir Cove - Ocean Manor Home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Boothbay Harbor Beach House by Park & Restaurants!, vacation rental in Southport

Boothbay Harbor Beach House by Park & Restaurants!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Water Views, Wrap Around Porch, 3 BR Coastal Home, vacation rental in Southport

Water Views, Wrap Around Porch, 3 BR Coastal Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Point, Maine Cottage Weekly Rental, vacation rental in Southport

Ocean Point, Maine Cottage Weekly Rental

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful waterfront home, vacation rental in Southport

Beautiful waterfront home

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Ocean Point Community, vacation rental in Southport

Beautiful Ocean Point Community

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Destination estate with exclusive views, privacy, and convenience, vacation rental in Southport

Destination estate with exclusive views, privacy, and convenience

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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The Hilltop Boothbay Harbor Steps from the Footbridge and in town dog friendly, vacation rental in Southport

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

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Tiny House Cottage, vacation rental in Southport

Tiny House Cottage

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Boothbay Harbor Cabin w/Spacious Deck & Yard!, vacation rental in Southport

Boothbay Harbor Cabin w/Spacious Deck & Yard!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Charming East Boothbay Cottage w/ Large Yard!, vacation rental in Southport

Charming East Boothbay Cottage w/ Large Yard!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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4 Bedroom Ocean Front cottage with glorious ocean views and deep water dock, vacation rental in Southport

4 Bedroom Ocean Front cottage with glorious ocean views and deep water dock

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming Cottage w/ Patio, Walk to Boothbay Harbor, vacation rental in Southport

Charming Cottage w/ Patio, Walk to Boothbay Harbor

4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! ‘Sprucewold’: Boothbay Harbor Cottage w/Deck, vacation rental in Southport

NEW! ‘Sprucewold’: Boothbay Harbor Cottage w/Deck

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor, vacation rental in Southport

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Carriage House In Beautiful Spruce Point, Pets Welcome, vacation rental in Southport

Luxury Carriage House In Beautiful Spruce Point, Pets Welcome

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Happy Trails Cottage, vacation rental in Southport

Happy Trails Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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