Southport, Maine

Vacation Rentals in Southport, Maine

Discover 31 vacation rental properties in Southport. From 1 to 6 bedrooms. Average $423/night. 100% have pools.

31 verified listings Book securely on VRBO Prices updated March 2026

31 properties available

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

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

1 bed 1 bath
PoolA/CWiFiBalcony
$250/night
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A Sweet Little Guest Cottage

A Sweet Little Guest Cottage

1 bed 1 bath
PoolA/CWiFiBalcony
$135/night
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The Ticket Office - Just the ticket for a Private & Romantic Getaway!

The Ticket Office - Just the ticket for a Private & Romantic Getaway!

1 bed 1 bath
PoolA/CWiFiBalcony
$180/night
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Charming Plumpoint Cottage On Southport Island

Charming Plumpoint Cottage On Southport Island

2 beds 1 bath
PoolA/CWiFiBalcony
$151/night
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental

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

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental

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

1 bed 1 bath
PoolA/CWiFiBalcony
$150/night
View Details → Book on VRBO
Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible

Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible

3 beds 2 baths
PoolA/CWiFiBalcony
$283/night
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Newly Renovated Upstairs Suite in 1790's Sea Captain's House on Deckers Cove

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

2 beds 2 baths
PoolA/CWiFiBalcony
$241/night
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Stunning oceanfront cottage w/ private deck and Atlantic views

Stunning oceanfront cottage w/ private deck and Atlantic views

3 beds 2 baths
PoolA/CWiFiBalcony
$278/night
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A Cozy Retreat on Southport Island

A Cozy Retreat on Southport Island

2 beds 1 bath
PoolA/CWiFiBalcony
$212/night
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Seawood Sunset Cottage: Southport Island

Seawood Sunset Cottage: Southport Island

2 beds 2 baths
PoolA/CWiFiBalcony
$328/night
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Remodeled for 2024! Immaculate Southport Island home. 5 minutes to Boothbay!

Remodeled for 2024! Immaculate Southport Island home. 5 minutes to Boothbay!

5 beds 2 baths
PoolA/CWiFiBalcony
$490/night
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Steamboat Landing Cottage

Steamboat Landing Cottage

4 beds 2 baths
PoolA/CWiFiBalcony
$456/night
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Two-Story Family-Friendly Home w/Free WiFi, Deck, Partial Ocean Views, and Grill

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

3 beds 1 bath
PoolA/CWiFiBalcony
$271/night
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Beachfront Delight with detached guesthouse, sunset views & private beach access

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

2 beds 2 baths
PoolA/CWiFiBalcony
$260/night
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Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck

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

4 beds 2 baths
PoolA/CWiFiBalcony
$328/night
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Cedar Cove: a tranquil retreat on the water just minutes from Boothbay Harbor

Cedar Cove: a tranquil retreat on the water just minutes from Boothbay Harbor

3 beds 2 baths
PoolA/CWiFiBalcony
$409/night
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Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!

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

4 beds 2 baths
PoolA/CWiFiBalcony
$613/night
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Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach

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

4 beds 1 bath
PoolA/CWiFiBalcony
$558/night
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Waterfront Home on Decker Cove

Waterfront Home on Decker Cove

4 beds 3 baths
PoolA/CWiFiBalcony
$718/night
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Spectacular Ocean Front Estate on Southport

Spectacular Ocean Front Estate on Southport

4 beds 3 baths
PoolA/CWiFiBalcony
$711/night
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Newly Renovated 3 B/2.5B Suite in 1790's Sea Captains House

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

3 beds 2 baths
PoolA/CWiFiBalcony
$325/night
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Pratts Island Get Away

Pratts Island Get Away

3 beds 2 baths
PoolA/CWiFiBalcony
$392/night
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A Picturesque Cottage on Capitol Island, Maine

A Picturesque Cottage on Capitol Island, Maine

4 beds 2 baths
PoolA/CWiFiBalcony
$370/night
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Decker Cove Southport Paradise with Central Air Conditioning

Decker Cove Southport Paradise with Central Air Conditioning

3 beds 3 baths
PoolA/CWiFiBalcony
$436/night
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Stunning Ocean Front Estate with a Private Dock

Stunning Ocean Front Estate with a Private Dock

6 beds 3 baths
PoolA/CWiFiBalcony
$1,731/night
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Boothbay area -- Newly renovated, near ocean, short drive to Botanical Gardens

Boothbay area -- Newly renovated, near ocean, short drive to Botanical Gardens

4 beds 3 baths
PoolA/CWiFiBalcony
$728/night
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Saltwater farmhouse on 2+ acres of waterfront with private dock

Saltwater farmhouse on 2+ acres of waterfront with private dock

5 beds 3 baths
PoolA/CWiFiBalcony
$728/night
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Ocean front cottage on a very private drive-on island in Boothbay Harbor, Maine

Ocean front cottage on a very private drive-on island in Boothbay Harbor, Maine

5 beds 2 baths
PoolA/CWiFiBalcony
$936/night
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Brand new in 2020 Cozy Cottage

Brand new in 2020 Cozy Cottage

2 beds 2 baths
PoolA/CWiFiBalcony
$166/night
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Coastal Cottage - Panoramic Views - Pond & Nature

Coastal Cottage - Panoramic Views - Pond & Nature

2 beds 1 bath
PoolA/CWiFiBalcony
$126/night
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More destinations in Maine

Old Orchard Beach (413) Wells (400) Bar Harbor (311) York (302) Portland (294) Ogunquit (254) Kennebunkport (216) Boothbay Harbor (206) Southwest Harbor (199) Kennebunk (199) Newry (192) Ellsworth (136) Scarborough (132) camden (105) Greenville (104) Harpswell (97) Mount Desert (96) Bethel (94) Mt Desert (64) Boothbay (63)