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Squirrel Island Vacation Rentals

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Bedrooms

Bathrooms

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5 mi
51 rentals in Squirrel Island.
Oceanfront home & guesthouse w/ incredible ocean views, deck & location!, vacation rental in Squirrel Island
Oceanfront home & guesthouse w/ incredible ocean views, deck & location!, vacation rental in Squirrel Island
Oceanfront home & guesthouse w/ incredible ocean views, deck & location!, vacation rental in Squirrel Island

Oceanfront home & guesthouse w/ incredible ocean views, deck & location!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace, vacation rental in Squirrel Island
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace, vacation rental in Squirrel Island
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace, vacation rental in Squirrel Island

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming Cottage on Ocean Point, vacation rental in Squirrel Island
Charming Cottage on Ocean Point, vacation rental in Squirrel Island
Charming Cottage on Ocean Point, vacation rental in Squirrel Island

Charming Cottage on Ocean Point

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Rustic Chic Cottage in Ocean Point! Water Views, Fireplace and Great Linens!, vacation rental in Squirrel Island
Rustic Chic Cottage in Ocean Point! Water Views, Fireplace and Great Linens!, vacation rental in Squirrel Island
Rustic Chic Cottage in Ocean Point! Water Views, Fireplace and Great Linens!, vacation rental in Squirrel Island

Rustic Chic Cottage in Ocean Point! Water Views, Fireplace and Great Linens!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Summer Cottage on Iconic Ocean Point, vacation rental in Squirrel Island
Beautiful Summer Cottage on Iconic Ocean Point, vacation rental in Squirrel Island
Beautiful Summer Cottage on Iconic Ocean Point, vacation rental in Squirrel Island

Beautiful Summer Cottage on Iconic Ocean Point

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sea Haven at Ocean Point, vacation rental in Squirrel Island
Sea Haven at Ocean Point, vacation rental in Squirrel Island
Sea Haven at Ocean Point, vacation rental in Squirrel Island

Sea Haven at Ocean Point

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Just one block from the Ocean!, vacation rental in Squirrel Island
Just one block from the Ocean!, vacation rental in Squirrel Island
Just one block from the Ocean!, vacation rental in Squirrel Island

Just one block from the Ocean!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Oceanfront family home w/ screened porch, amazing view & water access!, vacation rental in Squirrel Island
Oceanfront family home w/ screened porch, amazing view & water access!, vacation rental in Squirrel Island
Oceanfront family home w/ screened porch, amazing view & water access!, vacation rental in Squirrel Island

Oceanfront family home w/ screened porch, amazing view & water access!

Rental Home
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Darling Rustic Ocean Point Cottage, vacation rental in Squirrel Island
Darling Rustic Ocean Point Cottage, vacation rental in Squirrel Island
Darling Rustic Ocean Point Cottage, vacation rental in Squirrel Island

Darling Rustic Ocean Point Cottage

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Ocean Point Colony Home w/ Sunroom & Sweeping Ocean Views, vacation rental in Squirrel Island
Ocean Point Colony Home w/ Sunroom & Sweeping Ocean Views, vacation rental in Squirrel Island
Ocean Point Colony Home w/ Sunroom & Sweeping Ocean Views, vacation rental in Squirrel Island

Ocean Point Colony Home w/ Sunroom & Sweeping Ocean Views

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Stunning Views with Walks to the Beach, vacation rental in Squirrel Island
Stunning Views with Walks to the Beach, vacation rental in Squirrel Island
Stunning Views with Walks to the Beach, vacation rental in Squirrel Island

Stunning Views with Walks to the Beach

Rental Home
6 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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New Offering | Spruce Cabin on Ocean Point | East Boothbay | Spectacular Ocean, vacation rental in Squirrel Island
New Offering | Spruce Cabin on Ocean Point | East Boothbay | Spectacular Ocean, vacation rental in Squirrel Island
New Offering | Spruce Cabin on Ocean Point | East Boothbay | Spectacular Ocean, vacation rental in Squirrel Island

New Offering | Spruce Cabin on Ocean Point | East Boothbay | Spectacular Ocean

Rental Home
5 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The following properties within 20 miles of Squirrel Island match all your filters:
Cedar Cove: a tranquil retreat on the coast of Maine with modern amenities, vacation rental in Squirrel Island
Cedar Cove: a tranquil retreat on the coast of Maine with modern amenities, vacation rental in Squirrel Island
Cedar Cove: a tranquil retreat on the coast of Maine with modern amenities, vacation rental in Squirrel Island

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Partial Ocean Views! ADA Room with Fireplace+Porch, vacation rental in Squirrel Island
Partial Ocean Views! ADA Room with Fireplace+Porch, vacation rental in Squirrel Island
Partial Ocean Views! ADA Room with Fireplace+Porch, vacation rental in Squirrel Island

Partial Ocean Views! ADA Room with Fireplace+Porch

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Woodlandview Lodge with Fireplace + Spa Access, vacation rental in Squirrel Island
Woodlandview Lodge with Fireplace + Spa Access, vacation rental in Squirrel Island
Woodlandview Lodge with Fireplace + Spa Access, vacation rental in Squirrel Island

Woodlandview Lodge with Fireplace + Spa Access

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Bright ADA Lodge Room with Partial Ocean Views, vacation rental in Squirrel Island
Bright ADA Lodge Room with Partial Ocean Views, vacation rental in Squirrel Island
Bright ADA Lodge Room with Partial Ocean Views, vacation rental in Squirrel Island

Bright ADA Lodge Room with Partial Ocean Views

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming Cottage Room with Porch | Hot Tub + Pool, vacation rental in Squirrel Island
Charming Cottage Room with Porch | Hot Tub + Pool, vacation rental in Squirrel Island
Charming Cottage Room with Porch | Hot Tub + Pool, vacation rental in Squirrel Island

Charming Cottage Room with Porch | Hot Tub + Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Beautiful Room + Porch | Shared Pool + Hot Tub, vacation rental in Squirrel Island
Beautiful Room + Porch | Shared Pool + Hot Tub, vacation rental in Squirrel Island
Beautiful Room + Porch | Shared Pool + Hot Tub, vacation rental in Squirrel Island

Beautiful Room + Porch | Shared Pool + Hot Tub

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Lodge Room with Partial Ocean View | Pool + Spa, vacation rental in Squirrel Island
Lodge Room with Partial Ocean View | Pool + Spa, vacation rental in Squirrel Island
Lodge Room with Partial Ocean View | Pool + Spa, vacation rental in Squirrel Island

Lodge Room with Partial Ocean View | Pool + Spa

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Spa + Pool Access! Bright Woodland View Room, vacation rental in Squirrel Island
Spa + Pool Access! Bright Woodland View Room, vacation rental in Squirrel Island
Spa + Pool Access! Bright Woodland View Room, vacation rental in Squirrel Island

Spa + Pool Access! Bright Woodland View Room

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Relaxing Escape! Partial Oceanview Lodge Room, vacation rental in Squirrel Island
Relaxing Escape! Partial Oceanview Lodge Room, vacation rental in Squirrel Island
Relaxing Escape! Partial Oceanview Lodge Room, vacation rental in Squirrel Island

Relaxing Escape! Partial Oceanview Lodge Room

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Bright Oceanview Lodge Room | Private Porch + Spa, vacation rental in Squirrel Island
Bright Oceanview Lodge Room | Private Porch + Spa, vacation rental in Squirrel Island
Bright Oceanview Lodge Room | Private Porch + Spa, vacation rental in Squirrel Island

Bright Oceanview Lodge Room | Private Porch + Spa

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Luxury Cabin on Linekin Bay, vacation rental in Squirrel Island
Luxury Cabin on Linekin Bay, vacation rental in Squirrel Island
Luxury Cabin on Linekin Bay, vacation rental in Squirrel Island

Luxury Cabin on Linekin Bay

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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MORNING SUN | COUPLE`S RETREAT | WATERFRONT | PRIVATE BEACH, vacation rental in Squirrel Island
MORNING SUN | COUPLE`S RETREAT | WATERFRONT | PRIVATE BEACH, vacation rental in Squirrel Island
MORNING SUN | COUPLE`S RETREAT | WATERFRONT | PRIVATE BEACH, vacation rental in Squirrel Island

MORNING SUN | COUPLE`S RETREAT | WATERFRONT | PRIVATE BEACH

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town, vacation rental in Squirrel Island
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town, vacation rental in Squirrel Island
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town, vacation rental in Squirrel Island

Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island
Spruce Point Inn, vacation rental in Squirrel Island

Spruce Point Inn

Cabin
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Bright Cottage Close to Waterfront! Private Porch, vacation rental in Squirrel Island
Bright Cottage Close to Waterfront! Private Porch, vacation rental in Squirrel Island
Bright Cottage Close to Waterfront! Private Porch, vacation rental in Squirrel Island

Bright Cottage Close to Waterfront! Private Porch

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Come and enjoy our Boothbay Cottage, vacation rental in Squirrel Island
Come and enjoy our Boothbay Cottage, vacation rental in Squirrel Island
Come and enjoy our Boothbay Cottage, vacation rental in Squirrel Island

Come and enjoy our Boothbay Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Original Cottage Of Spruce Point Inn, vacation rental in Squirrel Island
Original Cottage Of Spruce Point Inn, vacation rental in Squirrel Island
Original Cottage Of Spruce Point Inn, vacation rental in Squirrel Island

Original Cottage Of Spruce Point Inn

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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PINE CLIFF DWELLER | SOUTHPORT ISLAND | OCEANFRONT | PRIVATE DOCK & FLOAT, vacation rental in Squirrel Island
PINE CLIFF DWELLER | SOUTHPORT ISLAND | OCEANFRONT | PRIVATE DOCK & FLOAT, vacation rental in Squirrel Island
PINE CLIFF DWELLER | SOUTHPORT ISLAND | OCEANFRONT | PRIVATE DOCK & FLOAT, vacation rental in Squirrel Island

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Cheerful Southport Island Waterfront Cottage, 'Tigin', vacation rental in Squirrel Island
Cheerful Southport Island Waterfront Cottage, 'Tigin', vacation rental in Squirrel Island
Cheerful Southport Island Waterfront Cottage, 'Tigin', vacation rental in Squirrel Island

Cheerful Southport Island Waterfront Cottage, 'Tigin'

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

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Waterfront Cottage With An Awesome View Of Capital And Burnt Island, vacation rental in Squirrel Island
Waterfront Cottage With An Awesome View Of Capital And Burnt Island, vacation rental in Squirrel Island
Waterfront Cottage With An Awesome View Of Capital And Burnt Island, vacation rental in Squirrel Island

Waterfront Cottage With An Awesome View Of Capital And Burnt Island

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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QUIET SPOT | EAST BOOTHBAY | LINEKIN BAY| FAMILY VACATION |, vacation rental in Squirrel Island

QUIET SPOT | EAST BOOTHBAY | LINEKIN BAY| FAMILY VACATION |

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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A Picturesque Cottage on Capitol Island, Maine, vacation rental in Squirrel Island
A Picturesque Cottage on Capitol Island, Maine, vacation rental in Squirrel Island
A Picturesque Cottage on Capitol Island, Maine, vacation rental in Squirrel Island

A Picturesque Cottage on Capitol Island, Maine

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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LEDGEMERE ON SOUTHPORT ISLAND | PET-FRIENDLY | BOLD OCEANFRONT | BEACH ACCESS |, vacation rental in Squirrel Island
LEDGEMERE ON SOUTHPORT ISLAND | PET-FRIENDLY | BOLD OCEANFRONT | BEACH ACCESS |, vacation rental in Squirrel Island
LEDGEMERE ON SOUTHPORT ISLAND | PET-FRIENDLY | BOLD OCEANFRONT | BEACH ACCESS |, vacation rental in Squirrel Island

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming Waterfront Cottage with Private Dock, vacation rental in Squirrel Island
Charming Waterfront Cottage with Private Dock, vacation rental in Squirrel Island
Charming Waterfront Cottage with Private Dock, vacation rental in Squirrel Island

Charming Waterfront Cottage with Private Dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Newly renovated, near ocean, vacation rental in Squirrel Island
Newly renovated, near ocean, vacation rental in Squirrel Island
Newly renovated, near ocean, vacation rental in Squirrel Island

Newly renovated, near ocean

Rental Home
4 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
More info
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Ocean front cottage on the coast of Maine., vacation rental in Squirrel Island
Ocean front cottage on the coast of Maine., vacation rental in Squirrel Island
Ocean front cottage on the coast of Maine., vacation rental in Squirrel Island

Ocean front cottage on the coast of Maine.

Rental Home
5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Oceanfront House on 2 acres, Sleeps 8, Use of SPI amenities (6 passes), vacation rental in Squirrel Island
Oceanfront House on 2 acres, Sleeps 8, Use of SPI amenities (6 passes), vacation rental in Squirrel Island
Oceanfront House on 2 acres, Sleeps 8, Use of SPI amenities (6 passes), vacation rental in Squirrel Island

Oceanfront House on 2 acres, Sleeps 8, Use of SPI amenities (6 passes)

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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PIFFI BIFF ON SOUTHPORT ISLAND | NEAR CAPE NEWAGEN | PET FRIENDLY | FAMILY, vacation rental in Squirrel Island
PIFFI BIFF ON SOUTHPORT ISLAND | NEAR CAPE NEWAGEN | PET FRIENDLY | FAMILY, vacation rental in Squirrel Island
PIFFI BIFF ON SOUTHPORT ISLAND | NEAR CAPE NEWAGEN | PET FRIENDLY | FAMILY, vacation rental in Squirrel Island

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-50 of 51
Frequently Asked Questions about Squirrel Island