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Holiday Homes in Long Island

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50 rentals in Long Island.
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Ocean View Cottage Falmouth Foreside, holiday rental in Long Island
Ocean View Cottage Falmouth Foreside, holiday rental in Long Island
Ocean View Cottage Falmouth Foreside, holiday rental in Long Island

Ocean View Cottage Falmouth Foreside

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Cozy Beach Cottage Just Minutes Walk From South Beach, Private, Screened Porch, holiday rental in Long Island
Cozy Beach Cottage Just Minutes Walk From South Beach, Private, Screened Porch, holiday rental in Long Island
Cozy Beach Cottage Just Minutes Walk From South Beach, Private, Screened Porch, holiday rental in Long Island

Cozy Beach Cottage Just Minutes Walk From South Beach, Private, Screened Porch

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Island Escape - Spacious 4 BR House with Car included!, holiday rental in Long Island
Island Escape - Spacious 4 BR House with Car included!, holiday rental in Long Island
Island Escape - Spacious 4 BR House with Car included!, holiday rental in Long Island

Island Escape - Spacious 4 BR House with Car included!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Oceanfront Villa 282, holiday rental in Long Island
Oceanfront Villa 282, holiday rental in Long Island
Oceanfront Villa 282, holiday rental in Long Island

Oceanfront Villa 282

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Home Sweet Home - Long Island, ME, holiday rental in Long Island
Home Sweet Home - Long Island, ME, holiday rental in Long Island
Home Sweet Home - Long Island, ME, holiday rental in Long Island

Home Sweet Home - Long Island, ME

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Seaside Island Home, holiday rental in Long Island
Beautiful Seaside Island Home, holiday rental in Long Island
Beautiful Seaside Island Home, holiday rental in Long Island

Beautiful Seaside Island Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Private Oceanfront Island Estate - Sleeps up to 22!, holiday rental in Long Island
Private Oceanfront Island Estate - Sleeps up to 22!, holiday rental in Long Island
Private Oceanfront Island Estate - Sleeps up to 22!, holiday rental in Long Island

Private Oceanfront Island Estate - Sleeps up to 22!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Grace Cottage, holiday rental in Long Island
Grace Cottage, holiday rental in Long Island
Grace Cottage, holiday rental in Long Island

Grace Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Brand New Island Rental, holiday rental in Long Island
Brand New Island Rental, holiday rental in Long Island
Brand New Island Rental, holiday rental in Long Island

Brand New Island Rental

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Sunset Landing 286 Oceanfront, holiday rental in Long Island
Sunset Landing 286 Oceanfront, holiday rental in Long Island
Sunset Landing 286 Oceanfront, holiday rental in Long Island

Sunset Landing 286 Oceanfront

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
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Charming Peaks Island Cottage, holiday rental in Long Island
Charming Peaks Island Cottage, holiday rental in Long Island
Charming Peaks Island Cottage, holiday rental in Long Island

Charming Peaks Island Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Oceanside Cottage On A Beautiful Sandy Beach - Enjoy Your Maine Vacation!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Charming, Secluded, Island Getaway!, holiday rental in Long Island
Charming, Secluded, Island Getaway!, holiday rental in Long Island
Charming, Secluded, Island Getaway!, holiday rental in Long Island

Charming, Secluded, Island Getaway!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Hollywood meets seaside charm in the former cottage of famed director, John Ford, holiday rental in Long Island
Hollywood meets seaside charm in the former cottage of famed director, John Ford, holiday rental in Long Island
Hollywood meets seaside charm in the former cottage of famed director, John Ford, holiday rental in Long Island

Hollywood meets seaside charm in the former cottage of famed director, John Ford

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location, holiday rental in Long Island
Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location, holiday rental in Long Island
Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location, holiday rental in Long Island

Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW LISTING ☼ Unique Oceanfront Home, holiday rental in Long Island
NEW LISTING ☼ Unique Oceanfront Home, holiday rental in Long Island
NEW LISTING ☼ Unique Oceanfront Home, holiday rental in Long Island

NEW LISTING ☼ Unique Oceanfront Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Long Island
The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Long Island
The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Long Island

The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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New Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Long Island
New Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Long Island
New Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Long Island

New Peaks Cottage: Modern amenities, island charm, steps to shore

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Falmouth Waterfront Carriage House Apt, holiday rental in Long Island
Falmouth Waterfront Carriage House Apt, holiday rental in Long Island
Falmouth Waterfront Carriage House Apt, holiday rental in Long Island

Falmouth Waterfront Carriage House Apt

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful getaway on Peaks Island!, holiday rental in Long Island
Beautiful getaway on Peaks Island!, holiday rental in Long Island
Beautiful getaway on Peaks Island!, holiday rental in Long Island

Beautiful getaway on Peaks Island!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Peaks Island Cottage with beautiful view of Whitehead passage, holiday rental in Long Island
Peaks Island Cottage with beautiful view of Whitehead passage, holiday rental in Long Island
Peaks Island Cottage with beautiful view of Whitehead passage, holiday rental in Long Island

Peaks Island Cottage with beautiful view of Whitehead passage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Adorable Peaks Island Cottage, holiday rental in Long Island
Adorable Peaks Island Cottage, holiday rental in Long Island
Adorable Peaks Island Cottage, holiday rental in Long Island

Adorable Peaks Island Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Great Diamond Island home w/water views-20 mins. by ferry from downtown Portland, holiday rental in Long Island
Great Diamond Island home w/water views-20 mins. by ferry from downtown Portland, holiday rental in Long Island
Great Diamond Island home w/water views-20 mins. by ferry from downtown Portland, holiday rental in Long Island

Great Diamond Island home w/water views-20 mins. by ferry from downtown Portland

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful House Rental At Diamond Cove At Great Diamond Island, holiday rental in Long Island
Beautiful House Rental At Diamond Cove At Great Diamond Island, holiday rental in Long Island
Beautiful House Rental At Diamond Cove At Great Diamond Island, holiday rental in Long Island

Beautiful House Rental At Diamond Cove At Great Diamond Island

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island, holiday rental in Long Island
Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island, holiday rental in Long Island
Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island, holiday rental in Long Island

Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Refurbished Brick, Waterfront Home on Cushing's Island., holiday rental in Long Island
Refurbished Brick, Waterfront Home on Cushing's Island., holiday rental in Long Island
Refurbished Brick, Waterfront Home on Cushing's Island., holiday rental in Long Island

Refurbished Brick, Waterfront Home on Cushing's Island.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Classic turn of the century Maine cottage - available May through October, holiday rental in Long Island
Classic turn of the century Maine cottage - available May through October, holiday rental in Long Island
Classic turn of the century Maine cottage - available May through October, holiday rental in Long Island

Classic turn of the century Maine cottage - available May through October

Holiday Rental House
0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning White Water Ocean Views From This Peaks Island Home, holiday rental in Long Island
Stunning White Water Ocean Views From This Peaks Island Home, holiday rental in Long Island
Stunning White Water Ocean Views From This Peaks Island Home, holiday rental in Long Island

Stunning White Water Ocean Views From This Peaks Island Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Evergreen cottage 5' from the water, holiday rental in Long Island
Evergreen cottage 5' from the water, holiday rental in Long Island
Evergreen cottage 5' from the water, holiday rental in Long Island

Evergreen cottage 5' from the water

Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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DIRECT OCEANFRONT Perfect location, holiday rental in Long Island
DIRECT OCEANFRONT Perfect location, holiday rental in Long Island
DIRECT OCEANFRONT Perfect location, holiday rental in Long Island

DIRECT OCEANFRONT Perfect location

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic Island Cottage, 5BR, holiday rental in Long Island
Historic Island Cottage, 5BR, holiday rental in Long Island
Historic Island Cottage, 5BR, holiday rental in Long Island

Historic Island Cottage, 5BR

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!, holiday rental in Long Island
Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!, holiday rental in Long Island
Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!, holiday rental in Long Island

Classic Summer Cottage With Full Amenities For Your Maine Island Vacation!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Island Village Cottage With Easy Ferry Ride to Portland, holiday rental in Long Island
Cozy Island Village Cottage With Easy Ferry Ride to Portland, holiday rental in Long Island
Cozy Island Village Cottage With Easy Ferry Ride to Portland, holiday rental in Long Island

Cozy Island Village Cottage With Easy Ferry Ride to Portland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season, holiday rental in Long Island
Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season, holiday rental in Long Island
Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season, holiday rental in Long Island

Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Peaks Island, easy to get to and harder to leave, holiday rental in Long Island
Peaks Island, easy to get to and harder to leave, holiday rental in Long Island
Peaks Island, easy to get to and harder to leave, holiday rental in Long Island

Peaks Island, easy to get to and harder to leave

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sunset Cottage, Family-Friendly Oasis, holiday rental in Long Island
Sunset Cottage, Family-Friendly Oasis, holiday rental in Long Island
Sunset Cottage, Family-Friendly Oasis, holiday rental in Long Island

Sunset Cottage, Family-Friendly Oasis

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Classic Maine Beach Cottage  *** Aug 2019 availability! Fabulous location!, holiday rental in Long Island
Classic Maine Beach Cottage  *** Aug 2019 availability! Fabulous location!, holiday rental in Long Island
Classic Maine Beach Cottage  *** Aug 2019 availability! Fabulous location!, holiday rental in Long Island

Classic Maine Beach Cottage *** Aug 2019 availability! Fabulous location!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Magical Rambling 5 Bedroom Cottage Built 1904 By John Calvin Stevens, holiday rental in Long Island
Magical Rambling 5 Bedroom Cottage Built 1904 By John Calvin Stevens, holiday rental in Long Island
Magical Rambling 5 Bedroom Cottage Built 1904 By John Calvin Stevens, holiday rental in Long Island

Magical Rambling 5 Bedroom Cottage Built 1904 By John Calvin Stevens

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Sunny, modern, family home w large yard. Summer on beautiful Peaks Island!, holiday rental in Long Island
Sunny, modern, family home w large yard. Summer on beautiful Peaks Island!, holiday rental in Long Island
Sunny, modern, family home w large yard. Summer on beautiful Peaks Island!, holiday rental in Long Island

Sunny, modern, family home w large yard. Summer on beautiful Peaks Island!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stunning views and comfort complete your ultimate Maine island vacation getaway., holiday rental in Long Island
Stunning views and comfort complete your ultimate Maine island vacation getaway., holiday rental in Long Island
Stunning views and comfort complete your ultimate Maine island vacation getaway., holiday rental in Long Island

Stunning views and comfort complete your ultimate Maine island vacation getaway.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Classic, cozy family cottage with modern amenities and ocean view from porch, holiday rental in Long Island
Classic, cozy family cottage with modern amenities and ocean view from porch, holiday rental in Long Island
Classic, cozy family cottage with modern amenities and ocean view from porch, holiday rental in Long Island

Classic, cozy family cottage with modern amenities and ocean view from porch

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Authentic Coastal Maine Cottage Living, holiday rental in Long Island
Authentic Coastal Maine Cottage Living, holiday rental in Long Island
Authentic Coastal Maine Cottage Living, holiday rental in Long Island

Authentic Coastal Maine Cottage Living

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch, holiday rental in Long Island
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch, holiday rental in Long Island
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch, holiday rental in Long Island

Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic Maine Beach Cottage, private beach access, holiday rental in Long Island
Classic Maine Beach Cottage, private beach access, holiday rental in Long Island
Classic Maine Beach Cottage, private beach access, holiday rental in Long Island

Classic Maine Beach Cottage, private beach access

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Renovated, Sunny 1850's Island Farmhouse, holiday rental in Long Island
Renovated, Sunny 1850's Island Farmhouse, holiday rental in Long Island
Renovated, Sunny 1850's Island Farmhouse, holiday rental in Long Island

Renovated, Sunny 1850's Island Farmhouse

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Backshore House Family friendly Oasis on Peaks Island, holiday rental in Long Island
The Backshore House Family friendly Oasis on Peaks Island, holiday rental in Long Island
The Backshore House Family friendly Oasis on Peaks Island, holiday rental in Long Island

The Backshore House Family friendly Oasis on Peaks Island

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in Long Island
Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in Long Island
Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in Long Island

Luxury Coastal Home w2 Living Rooms, Pool, Rooftop

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Ocean Views for Miles, Spectacular Sunrises at Ocean House, Peaks Island, Maine, holiday rental in Long Island
Ocean Views for Miles, Spectacular Sunrises at Ocean House, Peaks Island, Maine, holiday rental in Long Island
Ocean Views for Miles, Spectacular Sunrises at Ocean House, Peaks Island, Maine, holiday rental in Long Island

Ocean Views for Miles, Spectacular Sunrises at Ocean House, Peaks Island, Maine

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in Long Island
Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in Long Island
Luxury Coastal Home w2 Living Rooms, Pool, Rooftop, holiday rental in Long Island

Luxury Coastal Home w2 Living Rooms, Pool, Rooftop

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Ocean front cottage with private beach., holiday rental in Long Island
Ocean front cottage with private beach., holiday rental in Long Island
Ocean front cottage with private beach., holiday rental in Long Island

Ocean front cottage with private beach.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Long Island