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Five Islands Holiday Rentals

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50 rentals in Five Islands.
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Enjoy the stunning views while relaxing on the deck at East Ledge Cottage, holiday rental in Five Islands

Enjoy the stunning views while relaxing on the deck at East Ledge Cottage

3 bedrooms
3 bathrooms
Sleeps 6
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Boathouse cottage on water's edge, stunning view and your own pier, holiday rental in Five Islands

Boathouse cottage on water's edge, stunning view and your own pier

3 bedrooms
1 bathroom
Sleeps 6
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Peaceful Lake Waterfront with Swim Dock  &Kayaks! Full Kitchen! Heat & air!, holiday rental in Five Islands

Peaceful Lake Waterfront with Swim Dock &Kayaks! Full Kitchen! Heat & air!

1 bedroom
1 bathroom
Sleeps 4
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Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, holiday rental in Five Islands

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

4 bedrooms
3 bathrooms
Sleeps 8
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Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor, holiday rental in Five Islands

Year Round Luxury Waterfront Condo, Heart of Boothbay Harbor

3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Cottage On Water, Near Beach!!, holiday rental in Five Islands

Beautiful Cottage On Water, Near Beach!!

3 bedrooms
1 bathroom
Sleeps 6
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Scenic White Rocks Cottage on the Maine Coast, holiday rental in Five Islands

Scenic White Rocks Cottage on the Maine Coast

2 bedrooms
1 bathroom
Sleeps 6
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Beautiful Boothbay Harbor Waterfront Cottage with private dock, holiday rental in Five Islands

Beautiful Boothbay Harbor Waterfront Cottage with private dock

3 bedrooms
2 bathrooms
Sleeps 6
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Updated Cottage on Water’s Edge with Deepwater Boat Dock!, holiday rental in Five Islands

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

1 bedroom
1 bathroom
Sleeps 2
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Unique, romantic, motorless floating island  (Tessie Ann) w/ 4 hp skiff, holiday rental in Five Islands

Unique, romantic, motorless floating island (Tessie Ann) w/ 4 hp skiff

1 bedroom
1 bathroom
Sleeps 4
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Historic House Featured in March 2015 House Beautiful Magazine!, holiday rental in Five Islands

Historic House Featured in March 2015 House Beautiful Magazine!

5 bedrooms
3 bathrooms
Sleeps 13
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Cozy Home on Georgetown Island off the Coast of Maine, holiday rental in Five Islands

Cozy Home on Georgetown Island off the Coast of Maine

3 bedrooms
3 bathrooms
Sleeps 7
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Cool 4BR / 1 BA * Family Getaway Near Maine's Best Ocean Beaches, holiday rental in Five Islands

Cool 4BR / 1 BA * Family Getaway Near Maine's Best Ocean Beaches

4 bedrooms
1 bathroom
Sleeps 8
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New rental in Boothbay Harbor, try our 'Authentic 'Log Cabin in Maine, holiday rental in Five Islands

New rental in Boothbay Harbor, try our 'Authentic 'Log Cabin in Maine

2 bedrooms
2 bathrooms
Sleeps 4
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Oceanfront Cottage On Linekin Bay Boothbay Harbor, holiday rental in Five Islands

Oceanfront Cottage On Linekin Bay Boothbay Harbor

1 bedroom
1 bathroom
Sleeps 2
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In-town, cottage nestled in the woods, short walk to all harbor activities, holiday rental in Five Islands

In-town, cottage nestled in the woods, short walk to all harbor activities

2 bedrooms
1 bathroom
Sleeps 3
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Walking Distance To Shops, Restaurants And  Footbridge, holiday rental in Five Islands

Walking Distance To Shops, Restaurants And Footbridge

3 bedrooms
4 bathrooms
Sleeps 8
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Cedar Log Cabin in Boothbay Harbor, Maine, holiday rental in Five Islands

Cedar Log Cabin in Boothbay Harbor, Maine

3 bedrooms
2 bathrooms
Sleeps 5
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Enjoy the beautiful scenery., holiday rental in Five Islands

Enjoy the beautiful scenery.

4 bedrooms
2 bathrooms
Sleeps 6
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Waterfront Cottage with Screened Porch surrounded by conservation land, holiday rental in Five Islands

Waterfront Cottage with Screened Porch surrounded by conservation land

1 bedroom
1 bathroom
Sleeps 4
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Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen, holiday rental in Five Islands

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

2 bedrooms
1 bathroom
Sleeps 6
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A Water Getaway.  Vacation On A Houseboat in Maine, A Virtual Private Island., holiday rental in Five Islands

A Water Getaway. Vacation On A Houseboat in Maine, A Virtual Private Island.

1 bedroom
1 bathroom
Sleeps 5
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Heron Cove on Hodgdon Island, Boothbay, Maine, holiday rental in Five Islands

Heron Cove on Hodgdon Island, Boothbay, Maine

3 bedrooms
2 bathrooms
Sleeps 6
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Charming water view home overlooking Mill Cove w/ a large deck - near town, holiday rental in Five Islands

Charming water view home overlooking Mill Cove w/ a large deck - near town

2 bedrooms
2 bathrooms
Sleeps 4
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Lovely waterfront home, harbour-side setting, holiday rental in Five Islands

Lovely waterfront home, harbour-side setting

2 bedrooms
2 bathrooms
Sleeps 4
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Landings East...Classic Waterfront Coastal Home, holiday rental in Five Islands

Landings East...Classic Waterfront Coastal Home

2 bedrooms
2 bathrooms
Sleeps 4
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5 bedroom/2 bath Cottage with direct water view and access, holiday rental in Five Islands

5 bedroom/2 bath Cottage with direct water view and access

5 bedrooms
2 bathrooms
Sleeps 10
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Oceanfront  Cottage Southport 3 BR 2BA, Handicapped Accessible, holiday rental in Five Islands

Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible

3 bedrooms
2 bathrooms
Sleeps 7
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Inviting & rustic cabin w/wood-burning fireplace & grill- Enjoy a private beach!, holiday rental in Five Islands

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

1 bedroom
1 bathroom
Sleeps 4
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Lakeside 3 BR Cabin in Boothbay Harbor, holiday rental in Five Islands

Lakeside 3 BR Cabin in Boothbay Harbor

3 bedrooms
2 bathrooms
Sleeps 8
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Decker Cove Southport Paradise with Central Air Conditioning, holiday rental in Five Islands

Decker Cove Southport Paradise with Central Air Conditioning

3 bedrooms
3 bathrooms
Sleeps 6
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New listing! Beautiful, dog-friendly home w/ water views, deck, & gas fireplace, holiday rental in Five Islands

New listing! Beautiful, dog-friendly home w/ water views, deck, & gas fireplace

4 bedrooms
3 bathrooms
Sleeps 9
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3 BR, 1.5 BA home waterfront on Sheepscot River with a private dock & float, holiday rental in Five Islands

3 BR, 1.5 BA home waterfront on Sheepscot River with a private dock & float

3 bedrooms
2 bathrooms
Sleeps 6
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Look Out Over the Water from a Cottage in the Water, holiday rental in Five Islands

Look Out Over the Water from a Cottage in the Water

2 bedrooms
1 bathroom
Sleeps 4
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New listing! Oceanfront home w/amazing view, wrap-around deck & 2 fireplaces!, holiday rental in Five Islands

New listing! Oceanfront home w/amazing view, wrap-around deck & 2 fireplaces!

3 bedrooms
4 bathrooms
Sleeps 10
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Coastal Island Retreat -   Privacy and Convenience. Boat rental available., holiday rental in Five Islands

Coastal Island Retreat - Privacy and Convenience. Boat rental available.

3 bedrooms
2 bathrooms
Sleeps 8
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Contemporary home overlooking the Kennebec awaits your Summer vacation, holiday rental in Five Islands

Contemporary home overlooking the Kennebec awaits your Summer vacation

3 bedrooms
3 bathrooms
Sleeps 6
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Open Plan 1- Bedroom Apt. Woods & Water. Southport., holiday rental in Five Islands

Open Plan 1- Bedroom Apt. Woods & Water. Southport.

1 bedroom
1 bathroom
Sleeps 2
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Boothbay Harbor Beach House by Park & Restaurants!, holiday rental in Five Islands

Boothbay Harbor Beach House by Park & Restaurants!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful waterfront home, holiday rental in Five Islands

Beautiful waterfront home

2 bedrooms
2 bathrooms
Sleeps 4
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Destination estate with exclusive views, privacy, and convenience, holiday rental in Five Islands

Destination estate with exclusive views, privacy, and convenience

6 bedrooms
7 bathrooms
Sleeps 12
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The Hilltop Boothbay Harbor Steps from the Footbridge and in town dog friendly, holiday rental in Five Islands

The Hilltop Boothbay Harbor Steps from the Footbridge and in town dog friendly

3 bedrooms
1 bathroom
Sleeps 5
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Tiny House Cottage, holiday rental in Five Islands

Tiny House Cottage

1 bedroom
1 bathroom
Sleeps 2
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Boothbay Harbor Cabin w/Spacious Deck & Yard!, holiday rental in Five Islands

Boothbay Harbor Cabin w/Spacious Deck & Yard!

3 bedrooms
1 bathroom
Sleeps 8
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4 Bedroom Ocean Front cottage with glorious ocean views and deep water dock, holiday rental in Five Islands

4 Bedroom Ocean Front cottage with glorious ocean views and deep water dock

4 bedrooms
2 bathrooms
Sleeps 7
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NEW! ‘Sprucewold’: Boothbay Harbor Cottage w/Deck, holiday rental in Five Islands

NEW! ‘Sprucewold’: Boothbay Harbor Cottage w/Deck

2 bedrooms
1 bathroom
Sleeps 4
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Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor, holiday rental in Five Islands

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

5 bedrooms
2 bathrooms
Sleeps 10
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Historic Home | Popham Beach | Phippsburg Center, holiday rental in Five Islands

Historic Home | Popham Beach | Phippsburg Center

3 bedrooms
2 bathrooms
Sleeps 9
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Luxury Carriage House In Beautiful Spruce Point, Pets Welcome, holiday rental in Five Islands

Luxury Carriage House In Beautiful Spruce Point, Pets Welcome

1 bedroom
1 bathroom
Sleeps 2
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Happy Trails Cottage, holiday rental in Five Islands

Happy Trails Cottage

2 bedrooms
2 bathrooms
Sleeps 4
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