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Southport Vacation Rentals

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43 rentals in Southport.
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, vacation rental in Southport
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, vacation rental in Southport
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, vacation rental in Southport

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cedar Cove: a tranquil retreat on the coast of Maine with modern amenities, vacation rental in Southport
Cedar Cove: a tranquil retreat on the coast of Maine with modern amenities, vacation rental in Southport
Cedar Cove: a tranquil retreat on the coast of Maine with modern amenities, vacation rental in Southport

Cedar Cove: a tranquil retreat on the coast of Maine with modern amenities

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
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!, vacation rental in Southport
Updated Cottage on Water’s Edge with Deepwater Boat Dock!, vacation rental in Southport

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Renovated Upstairs Suite in 1790's Sea Captain's House on Deckers Cove, vacation rental in Southport
Newly Renovated Upstairs Suite in 1790's Sea Captain's House on Deckers Cove, vacation rental in Southport
Newly Renovated Upstairs Suite in 1790's Sea Captain's House on Deckers Cove, vacation rental in Southport

Newly Renovated Upstairs Suite in 1790's Sea Captain's House on Deckers Cove

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Southport

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Coastal Cottage - Panoramic Views - Pond & Nature, vacation rental in Southport
Coastal Cottage - Panoramic Views - Pond & Nature, vacation rental in Southport
Coastal Cottage - Panoramic Views - Pond & Nature, vacation rental in Southport

Coastal Cottage - Panoramic Views - Pond & Nature

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A Sweet Little Guest Cottage, vacation rental in Southport
A Sweet Little Guest Cottage, vacation rental in Southport
A Sweet Little Guest Cottage, vacation rental in Southport

A Sweet Little Guest Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Plumpoint Cottage On Southport Island, vacation rental in Southport
Charming Plumpoint Cottage On Southport Island, vacation rental in Southport
Charming Plumpoint Cottage On Southport Island, vacation rental in Southport

Charming Plumpoint Cottage On Southport Island

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront cottage, vacation rental in Southport
Waterfront cottage, vacation rental in Southport
Waterfront cottage, vacation rental in Southport

Waterfront cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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3 Bedroom Classic Maine Cottage, Close To Beach, vacation rental in Southport
3 Bedroom Classic Maine Cottage, Close To Beach, vacation rental in Southport
3 Bedroom Classic Maine Cottage, Close To Beach, vacation rental in Southport

3 Bedroom Classic Maine Cottage, Close To Beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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A Cozy Retreat on Southport Island, vacation rental in Southport
A Cozy Retreat on Southport Island, vacation rental in Southport
A Cozy Retreat on Southport Island, vacation rental in Southport

A Cozy Retreat on Southport Island

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Brand new in 2020 Cozy Cottage, vacation rental in Southport
Brand new in 2020 Cozy Cottage, vacation rental in Southport
Brand new in 2020 Cozy Cottage, vacation rental in Southport

Brand new in 2020 Cozy Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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PINE CLIFF DWELLER | SOUTHPORT ISLAND | OCEANFRONT | PRIVATE DOCK & FLOAT, vacation rental in Southport
PINE CLIFF DWELLER | SOUTHPORT ISLAND | OCEANFRONT | PRIVATE DOCK & FLOAT, vacation rental in Southport
PINE CLIFF DWELLER | SOUTHPORT ISLAND | OCEANFRONT | PRIVATE DOCK & FLOAT, vacation rental in Southport

PINE CLIFF DWELLER | SOUTHPORT ISLAND | OCEANFRONT | PRIVATE DOCK & FLOAT

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cheerful Southport Island Waterfront Cottage, 'Tigin', vacation rental in Southport
Cheerful Southport Island Waterfront Cottage, 'Tigin', vacation rental in Southport
Cheerful Southport Island Waterfront Cottage, 'Tigin', vacation rental in Southport

Cheerful Southport Island Waterfront Cottage, 'Tigin'

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Two-Story Family-Friendly Home w/Free WiFi, Deck, Partial Ocean Views, and Grill, vacation rental in Southport
Two-Story Family-Friendly Home w/Free WiFi, Deck, Partial Ocean Views, and Grill, vacation rental in Southport
Two-Story Family-Friendly Home w/Free WiFi, Deck, Partial Ocean Views, and Grill, vacation rental in Southport

Two-Story Family-Friendly Home w/Free WiFi, Deck, Partial Ocean Views, and Grill

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Southport Island Cottage | Deck & New Luxe Kitchen | Near Boothbay Harbor, vacation rental in Southport
Southport Island Cottage | Deck & New Luxe Kitchen | Near Boothbay Harbor, vacation rental in Southport
Southport Island Cottage | Deck & New Luxe Kitchen | Near Boothbay Harbor, vacation rental in Southport

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront Delight with detached guesthouse, sunset views & private beach access, vacation rental in Southport
Beachfront Delight with detached guesthouse, sunset views & private beach access, vacation rental in Southport
Beachfront Delight with detached guesthouse, sunset views & private beach access, vacation rental in Southport

Beachfront Delight with detached guesthouse, sunset views & private beach access

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Cottage With An Awesome View Of Capital And Burnt Island, vacation rental in Southport
Waterfront Cottage With An Awesome View Of Capital And Burnt Island, vacation rental in Southport
Waterfront Cottage With An Awesome View Of Capital And Burnt Island, vacation rental in Southport

Waterfront Cottage With An Awesome View Of Capital And Burnt Island

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pratts Island Get Away, vacation rental in Southport
Pratts Island Get Away, vacation rental in Southport
Pratts Island Get Away, vacation rental in Southport

Pratts Island Get Away

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic, vacation rental in Southport
Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic, vacation rental in Southport
Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic, vacation rental in Southport

Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
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, vacation rental in Southport
Oceanfront  Cottage Southport 3 BR 2BA, Handicapped Accessible, vacation rental in Southport

Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Breathtaking Water Views on Southport Island, vacation rental in Southport
Breathtaking Water Views on Southport Island, vacation rental in Southport
Breathtaking Water Views on Southport Island, vacation rental in Southport

Breathtaking Water Views on Southport Island

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning oceanfront cottage w/ private deck and Atlantic views, vacation rental in Southport
Stunning oceanfront cottage w/ private deck and Atlantic views, vacation rental in Southport
Stunning oceanfront cottage w/ private deck and Atlantic views, vacation rental in Southport

Stunning oceanfront cottage w/ private deck and Atlantic views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Picturesque Cottage on Capitol Island, Maine, vacation rental in Southport
A Picturesque Cottage on Capitol Island, Maine, vacation rental in Southport
A Picturesque Cottage on Capitol Island, Maine, vacation rental in Southport

A Picturesque Cottage on Capitol Island, Maine

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LEDGEMERE ON SOUTHPORT ISLAND | PET-FRIENDLY | BOLD OCEANFRONT | BEACH ACCESS |, vacation rental in Southport
LEDGEMERE ON SOUTHPORT ISLAND | PET-FRIENDLY | BOLD OCEANFRONT | BEACH ACCESS |, vacation rental in Southport
LEDGEMERE ON SOUTHPORT ISLAND | PET-FRIENDLY | BOLD OCEANFRONT | BEACH ACCESS |, vacation rental in Southport

LEDGEMERE ON SOUTHPORT ISLAND | PET-FRIENDLY | BOLD OCEANFRONT | BEACH ACCESS |

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Waterfront Cottage with Private Dock, vacation rental in Southport
Charming Waterfront Cottage with Private Dock, vacation rental in Southport
Charming Waterfront Cottage with Private Dock, vacation rental in Southport

Charming Waterfront Cottage with Private Dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated 3 B/2.5B Suite in 1790's Sea Captains House, vacation rental in Southport
Newly Renovated 3 B/2.5B Suite in 1790's Sea Captains House, vacation rental in Southport
Newly Renovated 3 B/2.5B Suite in 1790's Sea Captains House, vacation rental in Southport

Newly Renovated 3 B/2.5B Suite in 1790's Sea Captains House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach, vacation rental in Southport
Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach, vacation rental in Southport
Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach, vacation rental in Southport

Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Steamboat Landing Cottage, vacation rental in Southport
Steamboat Landing Cottage, vacation rental in Southport
Steamboat Landing Cottage, vacation rental in Southport

Steamboat Landing Cottage

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Log Cabin on Southport Island- 7 acres with westerly views, vacation rental in Southport
Waterfront Log Cabin on Southport Island- 7 acres with westerly views, vacation rental in Southport
Waterfront Log Cabin on Southport Island- 7 acres with westerly views, vacation rental in Southport

Waterfront Log Cabin on Southport Island- 7 acres with westerly views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
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, vacation rental in Southport
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor, vacation rental in Southport

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Newly renovated, near ocean, vacation rental in Southport
Newly renovated, near ocean, vacation rental in Southport
Newly renovated, near ocean, vacation rental in Southport

Newly renovated, near ocean

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Ocean front cottage on the coast of Maine., vacation rental in Southport
Ocean front cottage on the coast of Maine., vacation rental in Southport
Ocean front cottage on the coast of Maine., vacation rental in Southport

Ocean front cottage on the coast of Maine.

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
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, vacation rental in Southport
Decker Cove Southport Paradise with Central Air Conditioning, vacation rental in Southport

Decker Cove Southport Paradise with Central Air Conditioning

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A SLICE OF HEAVEN | SPECTACULAR OCEAN VIEWS | SUNRISE VIEWS | PET FRIENDLY, vacation rental in Southport
A SLICE OF HEAVEN | SPECTACULAR OCEAN VIEWS | SUNRISE VIEWS | PET FRIENDLY, vacation rental in Southport
A SLICE OF HEAVEN | SPECTACULAR OCEAN VIEWS | SUNRISE VIEWS | PET FRIENDLY, vacation rental in Southport

A SLICE OF HEAVEN | SPECTACULAR OCEAN VIEWS | SUNRISE VIEWS | PET FRIENDLY

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck, vacation rental in Southport
Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck, vacation rental in Southport
Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck, vacation rental in Southport

Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Ocean Front Estate on Southport, vacation rental in Southport
Spectacular Ocean Front Estate on Southport, vacation rental in Southport
Spectacular Ocean Front Estate on Southport, vacation rental in Southport

Spectacular Ocean Front Estate on Southport

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront home, vacation rental in Southport
Oceanfront home, vacation rental in Southport
Oceanfront home, vacation rental in Southport

Oceanfront home

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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PIFFI BIFF ON SOUTHPORT ISLAND | NEAR CAPE NEWAGEN | PET FRIENDLY | FAMILY, vacation rental in Southport
PIFFI BIFF ON SOUTHPORT ISLAND | NEAR CAPE NEWAGEN | PET FRIENDLY | FAMILY, vacation rental in Southport
PIFFI BIFF ON SOUTHPORT ISLAND | NEAR CAPE NEWAGEN | PET FRIENDLY | FAMILY, vacation rental in Southport

PIFFI BIFF ON SOUTHPORT ISLAND | NEAR CAPE NEWAGEN | PET FRIENDLY | FAMILY

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Saltwater farmhouse on 2+ acres of waterfront with private dock, vacation rental in Southport
Saltwater farmhouse on 2+ acres of waterfront with private dock, vacation rental in Southport
Saltwater farmhouse on 2+ acres of waterfront with private dock, vacation rental in Southport

Saltwater farmhouse on 2+ acres of waterfront with private dock

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Ocean Front Estate with a Private Dock, vacation rental in Southport
Stunning Ocean Front Estate with a Private Dock, vacation rental in Southport
Stunning Ocean Front Estate with a Private Dock, vacation rental in Southport

Stunning Ocean Front Estate with a Private Dock

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Showing results 1-43 of 43
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