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Squirrel Island Vacation Rentals

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50 rentals in Squirrel Island.
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Dog-friendly, bayfront home w/ gorgeous ocean views & a full kitchen, vacation rental in Squirrel Island

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Water Views, Wrap Around Porch, 3 BR Coastal Home, vacation rental in Squirrel Island

Water Views, Wrap Around Porch, 3 BR Coastal Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean front cottage with spectacular view, vacation rental in Squirrel Island

Ocean front cottage with spectacular view

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Unique Experience!!, vacation rental in Squirrel Island

A Unique Experience!!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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East Boothbay Waterfront One room Condo.Waterview from in side this room, vacation rental in Squirrel Island

East Boothbay Waterfront One room Condo.Waterview from in side this room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, vacation rental in Squirrel Island

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lobster Cove Lookout, vacation rental in Squirrel Island

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 Squirrel Island

Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful! Oceanfront Sunsets With Beach And Deep Water Access!, vacation rental in Squirrel Island

Peaceful! Oceanfront Sunsets With Beach And Deep Water Access!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Boothbay/Ocean Point 1/1 Air conditioned Oceanfront apartment, vacation rental in Squirrel Island

Boothbay/Ocean Point 1/1 Air conditioned Oceanfront apartment

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Our comfortable cottage sits on a dock close to town, over looking Lobster Cove, vacation rental in Squirrel Island

Our comfortable cottage sits on a dock close to town, over looking Lobster Cove

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquil!!  Oceanfront Sunsets with beach, pier,and deep water access, vacation rental in Squirrel Island

Tranquil!! Oceanfront Sunsets with beach, pier,and deep water access

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Waterfront Cottage!  2 Bedroom, 2 Bath  **Walk to Town*  1/2 Mile to the Harbor, vacation rental in Squirrel Island

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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Gorgeous Oceanfront Sunsets With Deep Water Access!, vacation rental in Squirrel Island

Gorgeous Oceanfront Sunsets With Deep Water Access!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relax & Enjoy Beautiful Views From This 2BR with Loft Cottage On the Sea, vacation rental in Squirrel Island

Relax & Enjoy Beautiful Views From This 2BR with Loft Cottage On the Sea

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic House Featured in March 2015 House Beautiful Magazine!, vacation rental in Squirrel Island

Historic House Featured in March 2015 House Beautiful Magazine!

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Updated Cottage on Water’s Edge with Deepwater Boat Dock!, vacation rental in Squirrel Island

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Classic Maine Waterfront Cottage w/ Deepwater Dock, vacation rental in Squirrel Island

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 Squirrel Island

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 Squirrel Island

Oceanfront Cottage On Linekin Bay Boothbay Harbor

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vintage Victorian Oceanfront with Deep Water Dock and Pool, vacation rental in Squirrel Island

Vintage Victorian Oceanfront with Deep Water Dock and Pool

6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Walking Distance To Shops, Restaurants And  Footbridge, vacation rental in Squirrel Island

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 Squirrel Island

Cedar Log Cabin in Boothbay Harbor, Maine

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Gorgeous sunsets on peaceful Linekin Bay coastal beach at low tide, dockfloat, vacation rental in Squirrel Island

Gorgeous sunsets on peaceful Linekin Bay coastal beach at low tide, dockfloat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Pointed Fir Cove: Stunning Ocean Front Maine Retreat for Discerning Vacationers!, vacation rental in Squirrel Island

Pointed Fir Cove: Stunning Ocean Front Maine Retreat for Discerning Vacationers!

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen, vacation rental in Squirrel Island

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quiet family and pet friendly home, vacation rental in Squirrel Island

Quiet family and pet friendly home

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect . Water . Paradise, vacation rental in Squirrel Island

Perfect . Water . Paradise

7 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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New listing! Oceanfront home w/ a wood stove, full kitchen, & stunning bay views, vacation rental in Squirrel Island

New listing! Oceanfront home w/ a wood stove, full kitchen, & stunning bay views

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 Squirrel Island

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 Squirrel Island

Lovely waterfront home, harbour-side setting

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Landings East...Classic Waterfront Coastal Home, vacation rental in Squirrel Island

Landings East...Classic Waterfront Coastal Home

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Decker Cove Southport Paradise with Central Air Conditioning, vacation rental in Squirrel Island

Decker Cove Southport Paradise with Central Air Conditioning

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront  Cottage Southport 3 BR 2BA, Handicapped Accessible, vacation rental in Squirrel Island

Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Inviting & rustic cabin w/wood-burning fireplace & grill- Enjoy a private beach!, vacation rental in Squirrel Island

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

2 bedrooms
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 Squirrel Island

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 Squirrel Island

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 Squirrel Island

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Family home w/ wood stove, game room, gas grill & garden views - 2 dogs OK!, vacation rental in Squirrel Island

Family home w/ wood stove, game room, gas grill & garden views - 2 dogs OK!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Pointed Fir Cove - Ocean Manor Home, vacation rental in Squirrel Island

Pointed Fir Cove - Ocean Manor Home

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Point, Maine Cottage Weekly Rental, vacation rental in Squirrel Island

Ocean Point, Maine Cottage Weekly Rental

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

Beautiful waterfront home

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

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 Squirrel Island

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 Squirrel Island

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 Squirrel Island

Tiny House Cottage

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2 bedroom  1 bath, large deck and dock, on the water in peaceful cove,   Year, vacation rental in Squirrel Island

2 bedroom 1 bath, large deck and dock, on the water in peaceful cove, Year

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pointed Fir Cove Cottage - Maine, vacation rental in Squirrel Island

Pointed Fir Cove Cottage - Maine

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Classic Home on Saltwater Pond in Secluded Oceanfront Neighborhood, vacation rental in Squirrel Island

Classic Home on Saltwater Pond in Secluded Oceanfront Neighborhood

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Carriage House In Beautiful Spruce Point, Pets Welcome, vacation rental in Squirrel Island

Luxury Carriage House In Beautiful Spruce Point, Pets Welcome

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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