Five Islands Vacation Rentals
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50 rentals in Five Islands.
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The best of Midcoast Maine; waterfront home, spectacular views, dog friendly!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Enjoy the stunning views while relaxing on the deck at East Ledge Cottage
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Cheerful Southport Isle Waterfront Cottage, 'An Tigin'
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Beautiful Cottage On Water, Near Beach!!
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Beautiful Boothbay Harbor Waterfront Cottage with private dock
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Unique, romantic, motorless floating island (Tessie Ann) w/ 4 hp skiff
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Historic House Featured in March 2015 House Beautiful Magazine!
Rental Home
6 bedrooms
3 bathrooms
Sleeps 13
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Updated Cottage on Water’s Edge with Deepwater Boat Dock!
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Cool 4BR / 1 BA * Family Getaway Near Maine's Best Ocean Beaches
Rental Home
4 bedrooms
1 bathroom
Sleeps 8
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Cozy Home on Georgetown Island off the Coast of Maine
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
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A Water Getaway. Vacation On A Houseboat in Maine, A Virtual Private Island.
Rental Home
1 bedroom
1 bathroom
Sleeps 5
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Romance and Adventure on the High Seas! The Charles Andrew with Motorized Skiff
Rental Home
1 bedroom
1 bathroom
Sleeps 5
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Waterfront Cottage with Screened Porch surrounded by conservation land
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Saltwater farmhouse on 2+ acres of waterfront with private dock
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Oceanfront Family Retreat + Dock + Walk to Town + Lobster wharf + Fire pit
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
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Maine Waterfront Cottage With Deep Water Dock!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
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Picturesque Waterfront Cottage with Wraparound Screen Porch
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Waterfront Cape Home for Tranquil Vacationing
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
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Cottage Overlooking Water
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Decker Cove Southport Paradise with Central Air Conditioning
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Cottage on the Water with Beatiful View
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Charming, peaceful 1 bedroom cottage with a serene waterfront view
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Classic Maine Cottage with Screen Porch
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Modern, Sunsets, Solitude, Swimming, Boating, close to Lobster and State Parks!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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A Cozy Retreat on Southport Island
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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New listing! Oceanfront home w/amazing view, wrap-around deck & 2 fireplaces!
Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
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Charming cottage overlooking picturesque Five Islands Harbor
Rental Home
3 bedrooms
1 bathroom
Sleeps 5
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New listing! Unique oceanfront home w/ wall of windows & amazing view!
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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NEW! Scenic Oceanfront Cottage w/ Deck & Near Town
Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
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Capitol Island, Waterfront, Kayaks, Tennis, Beach, Spectacular Sunrises, Sunsets
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
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Coastal Island Retreat - Privacy and Convenience. Boat rental available.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Open Plan 1- Bedroom Apt. Woods & Water. Southport.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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Relax over looking the quaint Five Islands Harbor in Georgetown Maine
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Sweet Little Guest Cottage Perfect for Two
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Island Cottage with Water Views on Both Sides
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
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Sprucerock Cabin - Escape to the Sounds of the Sea and Breathtaking Views
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Three Bedroom Cottage on Southport Island overlooking Decker Cove
Rental Home
3 bedrooms
2 bathrooms
Sleeps 2
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Welcoming vacation home offers a private setting on the water's edge
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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4 Bedroom Ocean Front cottage with glorious ocean views and deep water dock
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
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Classic Maine Cottage on Juniper Point with Ocean Views and Steps to Beach
Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
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Contemporary Cottage Nestled in the Pines at The Ocean’s Edge
Rental Home
3 bedrooms
1 bathroom
Sleeps 2
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Unique Contemporary Waterfront 4 bedroom house on gorgeous peninsula lot
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Log Cabin on Southport Isl,10 acres, 400' waterfrt, deepwater dock, sunset views
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
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Waterfront home near Reid State Park
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Frequently Asked Questions about Five Islands
- Yes, here are some popular vacation rentals in Five Islands that have a pool:\n
- \n
- Enjoy the stunning views while relaxing on the deck at East Ledge Cottage \n
- The best of Midcoast Maine; waterfront home, spectacular views, dog friendly! \n
- Coastal Island Retreat - Privacy and Convenience. Boat rental available. \n
- Yes, here are some popular vacation rentals in Five Islands that have internet access:\n
- \n
- Enjoy the stunning views while relaxing on the deck at East Ledge Cottage \n
- The best of Midcoast Maine; waterfront home, spectacular views, dog friendly! \n
- Cottage Overlooking Water \n
- The best pet friendly rentals in Five Islands are:\n
- \n
- Enjoy the stunning views while relaxing on the deck at East Ledge Cottage \n
- The best of Midcoast Maine; waterfront home, spectacular views, dog friendly! \n
- Coastal Island Retreat - Privacy and Convenience. Boat rental available. \n
- Some of the most popular kid friendly rentals in Five Islands are:\n
- \n
- The best of Midcoast Maine; waterfront home, spectacular views, dog friendly! \n
- Enjoy the stunning views while relaxing on the deck at East Ledge Cottage \n
- Coastal Island Retreat - Privacy and Convenience. Boat rental available. \n