Southport Vacation Rentals, Houses & More


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OCEAN WAY | SOUTHPORT ISLAND | QUIET WOODLAND RETREAT | LOCAL BEACHES | BICYCLE

  • 2
  • 4
  • Min stay varies

Inquire for Rates

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Great rentals within 30 miles that match your search

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PIFFI BIFF| SOUTHPORT ISLAND | NEAR CAPE NEWAGEN | BOOTHBAY PENINSULA| GREAT

  • 5
  • 10
  • Min stay varies

$411

Details

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MOLLYS CAPE | SOUTHPORT ISLAND | OCEAN VIEWS | SHARED BEACH | KAYAKERS DREAM

  • 3
  • 6
  • Min stay varies

$465

Details

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BARNACLES COTTAGE | SOUTHPORT ISLAND | PRIVATE BEACH | PET FRIENDLY | QUIET

  • 2
  • 4
  • Min stay varies

$387

Details

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SOUTHPORT Waterfront Tidewater Farm with dock

  • 4
  • 6
  • 7 nights min

$358

Details

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SOUTHPORT waterfront historic farmhouse w dock

  • 4
  • 6
  • 7 nights min

$400

Details

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Oceanfront contemporary home with stunning island and lighthouse views

  • 3
  • 6
  • Min stay varies

$80

Details

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JOHNS COTTAGE | MCKOWN POINT | JUNIPER POINT ASSOCIATION | OCEAN FRONT | OCEAN

  • 5
  • 10
  • Min stay varies

$287

Details

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THREE SEAS | MCKOWN POINT | JUNIPER POINT ASSOCIATION | ASSOCIATION BEACH, DOCK

  • 2
  • 4
  • Min stay varies

$211

Details

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LEDGEMERE | SOUTHPORT ISLAND | BOLD OCEANFRONT | ISLANDS | LIGHTHOUSE

  • 3
  • 6
  • Min stay varies

$318

Details

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Elegant and inviting plantation-style home with two levels of wrap-around decks

  • 4
  • 7
  • 2 nights min

$136

Details

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Charming, dog-friendly cottage near aquarium - minutes from Boothbay Harbor!

  • 3
  • 6
  • Min stay varies

$99

Details

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Lakefront home w/ a private dock, canoe, kayak, fishing equipment & two decks!

  • 4
  • 8
  • Min stay varies

$350

Details

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LAZY DAYS | SPRUCE POINT | BOOTHBAY HARBOR, MAINE | WATER-FRONT| VIEWS INTO

  • 4
  • 7
  • Min stay varies

$358

Details

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SPRUCE POINT ESTATE | KAYAKING, BOATING, BIKING AND MORE! | PET-FRIENDLY

  • 5
  • 10
  • Min stay varies

$909

Details

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ATLANTIC SUNSET | SPRUCE POINT | OCEAN FRONT | KAYAKING | PET-FRIENDLY

  • 7
  • 12
  • Min stay varies

$748

Details

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3BR Waterfront Home w/ Backyard Kayak Launch – 5 Mins to Botanical Gardens

  • 3
  • 6
  • 2 nights min

$248

Details

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LA CABINITA | BOOTHBAY HARBOR | SPRUCEWOLD COMMUNITY | SECLUDED SETTING | GREAT

  • 3
  • 6
  • Min stay varies

$183

Details

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MERWICK COTTAGE | FIVE ISLANDS | GEORGETOWN, MAINE | WATER-FRONT| OCEAN VIEWS

  • 3
  • 6
  • Min stay varies

$269

Details

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Waterfront House with Views of Working Harbor and Open Ocean from Every Room

  • 4
  • 7
  • 7 nights min

$250

Details

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Enchanting bayview home close to the beach scene and local attractions

  • 3
  • 4
  • Min stay varies

$99

Details

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Vintage, log cabin w/ beach club access, very close to harbor

  • 2
  • 4
  • Min stay varies

$99

Details

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Beautiful waterfront home

  • 2
  • 4
  • 7 nights min

$208

Details

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Chic Studio Cabin in Boothbay Harbor: Ocean Views, Sprucewold Beach Access

  • 2
  • Min stay varies

$129

Details

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Classic and dog-friendly house w/grassy yard, near area shopping!

  • 4
  • 8
  • Min stay varies

$176

Details

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Boothbay Harbor Pet-Friendly High-Tech House Lake Access Near Ocean

  • 3
  • 8
  • Min stay varies

$160

Details

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The Coal Shack: Pet-Friendly Harborfront Studio in Downtown Boothbay

  • 2
  • Min stay varies

$139

Details

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3BR in Downtown Boothbay Harbor, On the Shore of Mill Cove

  • 3
  • 6
  • Min stay varies

$205

Details

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Buddy’s Barrel House: Pet-Friendly 3BR Apartment in Downtown Boothbay

  • 3
  • 8
  • Min stay varies

$425

Details

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Mavooshen Retreat at Sprucewold, Private Beach Access, Minutes to Downtown

  • 2
  • 4
  • Min stay varies

$172

Details

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Cedar Log Cabin in Boothbay Harbor, Maine

  • 3
  • 5
  • Min stay varies

$175

Details

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EDGE OF THE SEA | OCEANFRONT | OCEAN POINT | EAST BOOTHBAY MAINE | LIGHTHOUSES

  • 3
  • 6
  • Min stay varies

$423

Details

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Historic Cape Cod with Harbor View, Featured in Coastal Living Magazine!

  • 3
  • 6
  • Min stay varies

$204

Details

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Mackerel Sky Suite

  • 1
  • 2
  • Min stay varies

$110

Details

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Sunny Brae, Modern Sprucewold Log Cabin With Beach Access

  • 2
  • 4
  • Min stay varies

$150

Details

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New England 1890 House with part water view

  • 1
  • 2
  • 7 nights min

$114

Details

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