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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!, vacation rental in Five Islands
The best of Midcoast Maine; waterfront home, spectacular views, dog friendly!, vacation rental in Five Islands
The best of Midcoast Maine; waterfront home, spectacular views, dog friendly!, vacation rental in Five Islands

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, vacation rental in Five Islands
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage, vacation rental in Five Islands
Enjoy the stunning views while relaxing on the deck at East Ledge Cottage, vacation rental in Five Islands

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!, vacation rental in Five Islands
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, vacation rental in Five Islands
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!, vacation rental in Five Islands

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', vacation rental in Five Islands
Cheerful Southport Isle Waterfront Cottage, 'An Tigin', vacation rental in Five Islands
Cheerful Southport Isle Waterfront Cottage, 'An Tigin', vacation rental in Five Islands

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!!, vacation rental in Five Islands
Beautiful Cottage On Water, Near Beach!!, vacation rental in Five Islands
Beautiful Cottage On Water, Near Beach!!, vacation rental in Five Islands

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, vacation rental in Five Islands
Beautiful Boothbay Harbor Waterfront Cottage with private dock, vacation rental in Five Islands
Beautiful Boothbay Harbor Waterfront Cottage with private dock, vacation rental in Five Islands

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, vacation rental in Five Islands
Unique, romantic, motorless floating island  (Tessie Ann) w/ 4 hp skiff, vacation rental in Five Islands
Unique, romantic, motorless floating island  (Tessie Ann) w/ 4 hp skiff, vacation rental in Five Islands

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!, vacation rental in Five Islands
Historic House Featured in March 2015 House Beautiful Magazine!, vacation rental in Five Islands
Historic House Featured in March 2015 House Beautiful Magazine!, vacation rental in Five Islands

Historic House Featured in March 2015 House Beautiful Magazine!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Updated Cottage on Water’s Edge with Deepwater Boat Dock!, vacation rental in Five Islands
Updated Cottage on Water’s Edge with Deepwater Boat Dock!, vacation rental in Five Islands
Updated Cottage on Water’s Edge with Deepwater Boat Dock!, vacation rental in Five Islands

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cool 4BR / 1 BA * Family Getaway Near Maine's Best Ocean Beaches, vacation rental in Five Islands
Cool 4BR / 1 BA * Family Getaway Near Maine's Best Ocean Beaches, vacation rental in Five Islands
Cool 4BR / 1 BA * Family Getaway Near Maine's Best Ocean Beaches, vacation rental in Five Islands

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, vacation rental in Five Islands
Cozy Home on Georgetown Island off the Coast of Maine, vacation rental in Five Islands
Cozy Home on Georgetown Island off the Coast of Maine, vacation rental in Five Islands

Cozy Home on Georgetown Island off the Coast of Maine

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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A Water Getaway.  Vacation On A Houseboat in Maine, A Virtual Private Island., vacation rental in Five Islands
A Water Getaway.  Vacation On A Houseboat in Maine, A Virtual Private Island., vacation rental in Five Islands
A Water Getaway.  Vacation On A Houseboat in Maine, A Virtual Private Island., vacation rental in Five Islands

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, vacation rental in Five Islands
Romance and Adventure on the High Seas!  The Charles Andrew with Motorized Skiff, vacation rental in Five Islands
Romance and Adventure on the High Seas!  The Charles Andrew with Motorized Skiff, vacation rental in Five Islands

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, vacation rental in Five Islands
Waterfront Cottage with Screened Porch surrounded by conservation land, vacation rental in Five Islands
Waterfront Cottage with Screened Porch surrounded by conservation land, vacation rental in Five Islands

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, vacation rental in Five Islands
Saltwater farmhouse on 2+ acres of waterfront with private dock, vacation rental in Five Islands
Saltwater farmhouse on 2+ acres of waterfront with private dock, vacation rental in Five Islands

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, vacation rental in Five Islands
Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen, vacation rental in Five Islands
Cozy, dog-friendly cabin w/ a wood burning fireplace & a full kitchen, vacation rental in Five Islands

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, vacation rental in Five Islands
Oceanfront Family Retreat + Dock + Walk to Town + Lobster wharf + Fire pit, vacation rental in Five Islands
Oceanfront Family Retreat + Dock + Walk to Town + Lobster wharf + Fire pit, vacation rental in Five Islands

Oceanfront Family Retreat + Dock + Walk to Town + Lobster wharf + Fire pit

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Maine Waterfront Cottage With Deep Water Dock!, vacation rental in Five Islands
Maine Waterfront Cottage With Deep Water Dock!, vacation rental in Five Islands
Maine Waterfront Cottage With Deep Water Dock!, vacation rental in Five Islands

Maine Waterfront Cottage With Deep Water Dock!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Picturesque Waterfront Cottage with Wraparound Screen Porch, vacation rental in Five Islands
Picturesque Waterfront Cottage with Wraparound Screen Porch, vacation rental in Five Islands
Picturesque Waterfront Cottage with Wraparound Screen Porch, vacation rental in Five Islands

Picturesque Waterfront Cottage with Wraparound Screen Porch

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Cape Home for Tranquil Vacationing, vacation rental in Five Islands
Waterfront Cape Home for Tranquil Vacationing, vacation rental in Five Islands
Waterfront Cape Home for Tranquil Vacationing, vacation rental in Five Islands

Waterfront Cape Home for Tranquil Vacationing

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cottage Overlooking Water, vacation rental in Five Islands
Cottage Overlooking Water, vacation rental in Five Islands
Cottage Overlooking Water, vacation rental in Five Islands

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, vacation rental in Five Islands
Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic, vacation rental in Five Islands
Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic, vacation rental in Five Islands

Oceanfront Juniper Point Cottage with dock, screened porch, close boat traffic

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Decker Cove Southport Paradise with Central Air Conditioning, vacation rental in Five Islands
Decker Cove Southport Paradise with Central Air Conditioning, vacation rental in Five Islands
Decker Cove Southport Paradise with Central Air Conditioning, vacation rental in Five Islands

Decker Cove Southport Paradise with Central Air Conditioning

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cottage on the Water with Beatiful View, vacation rental in Five Islands
Cottage on the Water with Beatiful View, vacation rental in Five Islands
Cottage on the Water with Beatiful View, vacation rental in Five Islands

Cottage on the Water with Beatiful View

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming, peaceful 1 bedroom cottage with a serene waterfront view, vacation rental in Five Islands
Charming, peaceful 1 bedroom cottage with a serene waterfront view, vacation rental in Five Islands
Charming, peaceful 1 bedroom cottage with a serene waterfront view, vacation rental in Five Islands

Charming, peaceful 1 bedroom cottage with a serene waterfront view

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Classic Maine Cottage with Screen Porch, vacation rental in Five Islands
Classic Maine Cottage with Screen Porch, vacation rental in Five Islands
Classic Maine Cottage with Screen Porch, vacation rental in Five Islands

Classic Maine Cottage with Screen Porch

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern, Sunsets, Solitude, Swimming, Boating, close to Lobster and State Parks!, vacation rental in Five Islands
Modern, Sunsets, Solitude, Swimming, Boating, close to Lobster and State Parks!, vacation rental in Five Islands
Modern, Sunsets, Solitude, Swimming, Boating, close to Lobster and State Parks!, vacation rental in Five Islands

Modern, Sunsets, Solitude, Swimming, Boating, close to Lobster and State Parks!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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A  Cozy Retreat on Southport Island, vacation rental in Five Islands
A  Cozy Retreat on Southport Island, vacation rental in Five Islands
A  Cozy Retreat on Southport Island, vacation rental in Five Islands

A Cozy Retreat on Southport Island

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

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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming cottage overlooking  picturesque Five Islands Harbor, vacation rental in Five Islands
Charming cottage overlooking  picturesque Five Islands Harbor, vacation rental in Five Islands
Charming cottage overlooking  picturesque Five Islands Harbor, vacation rental in Five Islands

Charming cottage overlooking picturesque Five Islands Harbor

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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New listing! Unique oceanfront home w/ wall of windows & amazing view!, vacation rental in Five Islands
New listing! Unique oceanfront home w/ wall of windows & amazing view!, vacation rental in Five Islands
New listing! Unique oceanfront home w/ wall of windows & amazing view!, vacation rental in Five Islands

New listing! Unique oceanfront home w/ wall of windows & amazing view!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Scenic Oceanfront Cottage w/ Deck & Near Town, vacation rental in Five Islands
NEW! Scenic Oceanfront Cottage w/ Deck & Near Town, vacation rental in Five Islands
NEW! Scenic Oceanfront Cottage w/ Deck & Near Town, vacation rental in Five Islands

NEW! Scenic Oceanfront Cottage w/ Deck & Near Town

Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Capitol Island, Waterfront, Kayaks, Tennis, Beach, Spectacular Sunrises, Sunsets, vacation rental in Five Islands
Capitol Island, Waterfront, Kayaks, Tennis, Beach, Spectacular Sunrises, Sunsets, vacation rental in Five Islands
Capitol Island, Waterfront, Kayaks, Tennis, Beach, Spectacular Sunrises, Sunsets, vacation rental in Five Islands

Capitol Island, Waterfront, Kayaks, Tennis, Beach, Spectacular Sunrises, Sunsets

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Coastal Island Retreat -   Privacy and Convenience. Boat rental available., vacation rental in Five Islands
Coastal Island Retreat -   Privacy and Convenience. Boat rental available., vacation rental in Five Islands
Coastal Island Retreat -   Privacy and Convenience. Boat rental available., vacation rental in Five Islands

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Open Plan 1- Bedroom Apt. Woods & Water. Southport., vacation rental in Five Islands
Open Plan 1- Bedroom Apt. Woods & Water. Southport., vacation rental in Five Islands
Open Plan 1- Bedroom Apt. Woods & Water. Southport., vacation rental in Five Islands

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Relax over looking the quaint Five Islands Harbor in Georgetown Maine, vacation rental in Five Islands
Relax over looking the quaint Five Islands Harbor in Georgetown Maine, vacation rental in Five Islands
Relax over looking the quaint Five Islands Harbor in Georgetown Maine, vacation rental in Five Islands

Relax over looking the quaint Five Islands Harbor in Georgetown Maine

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sweet Little Guest Cottage Perfect for Two, vacation rental in Five Islands
Sweet Little Guest Cottage Perfect for Two, vacation rental in Five Islands
Sweet Little Guest Cottage Perfect for Two, vacation rental in Five Islands

Sweet Little Guest Cottage Perfect for Two

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Island Cottage with  Water Views on Both Sides, vacation rental in Five Islands
Island Cottage with  Water Views on Both Sides, vacation rental in Five Islands
Island Cottage with  Water Views on Both Sides, vacation rental in Five Islands

Island Cottage with Water Views on Both Sides

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sprucerock Cabin - Escape to the Sounds of the Sea and Breathtaking Views, vacation rental in Five Islands
Sprucerock Cabin - Escape to the Sounds of the Sea and Breathtaking Views, vacation rental in Five Islands
Sprucerock Cabin - Escape to the Sounds of the Sea and Breathtaking Views, vacation rental in Five Islands

Sprucerock Cabin - Escape to the Sounds of the Sea and Breathtaking Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands
3 one-bedroom fully equipped cottages with free WIFI /weekly rental, vacation rental in Five Islands

3 one-bedroom fully equipped cottages with free WIFI /weekly rental

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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, vacation rental in Five Islands
Welcoming vacation home offers a private setting on the water's edge, vacation rental in Five Islands
Welcoming vacation home offers a private setting on the water's edge, vacation rental in Five Islands

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, vacation rental in Five Islands
4 Bedroom Ocean Front cottage with glorious ocean views and deep water dock, vacation rental in Five Islands
4 Bedroom Ocean Front cottage with glorious ocean views and deep water dock, vacation rental in Five Islands

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Classic Maine Cottage on Juniper Point with Ocean Views and Steps to Beach, vacation rental in Five Islands
Classic Maine Cottage on Juniper Point with Ocean Views and Steps to Beach, vacation rental in Five Islands
Classic Maine Cottage on Juniper Point with Ocean Views and Steps to Beach, vacation rental in Five Islands

Classic Maine Cottage on Juniper Point with Ocean Views and Steps to Beach

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Contemporary Cottage Nestled in the Pines at The Ocean’s Edge, vacation rental in Five Islands
Contemporary Cottage Nestled in the Pines at The Ocean’s Edge, vacation rental in Five Islands
Contemporary Cottage Nestled in the Pines at The Ocean’s Edge, vacation rental in Five Islands

Contemporary Cottage Nestled in the Pines at The Ocean’s Edge

Rental Home
3 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Unique Contemporary Waterfront 4 bedroom house on gorgeous peninsula lot, vacation rental in Five Islands
Unique Contemporary Waterfront 4 bedroom house on gorgeous peninsula lot, vacation rental in Five Islands
Unique Contemporary Waterfront 4 bedroom house on gorgeous peninsula lot, vacation rental in Five Islands

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, vacation rental in Five Islands
Log Cabin on Southport Isl,10 acres, 400' waterfrt, deepwater dock, sunset views, vacation rental in Five Islands
Log Cabin on Southport Isl,10 acres, 400' waterfrt, deepwater dock, sunset views, vacation rental in Five Islands

Log Cabin on Southport Isl,10 acres, 400' waterfrt, deepwater dock, sunset views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Waterfront home near Reid State Park, vacation rental in Five Islands
Waterfront home near Reid State Park, vacation rental in Five Islands
Waterfront home near Reid State Park, vacation rental in Five Islands

Waterfront home near Reid State Park

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Five Islands