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Holiday Rentals 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

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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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!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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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!

3 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Grace Cottage, holiday rental in Long Island

Grace Cottage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Seaside Island Home, holiday rental in Long Island

Beautiful Seaside Island Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Waterfront Casco Bay Retreat with Private Deep Water Dock.  Doggie Friendly!, holiday rental in Long Island

A Waterfront Casco Bay Retreat with Private Deep Water Dock. Doggie Friendly!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Glorious getaway on Portland's Eastern Promenade., holiday rental in Long Island

Glorious getaway on Portland's Eastern Promenade.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Oceanside Cottage On A Beautiful Sandy Beach - Enjoy Your Maine Vacation!, holiday rental in Long Island

Oceanside Cottage On A Beautiful Sandy Beach - Enjoy Your Maine Vacation!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Falmouth Furnished 3 Bedroom 2 Bath Loft Close to Portland, holiday rental in Long Island

Beautiful Falmouth Furnished 3 Bedroom 2 Bath Loft Close to Portland

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3BR home: East End neighborhood: walk to ocean or downtown, local eateries, holiday rental in Long Island

3BR home: East End neighborhood: walk to ocean or downtown, local eateries

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Long Island

Charming 2-bedroom steps from the Eastern Promenade

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Sleek Condo w/ a Private Patio - Less than Two Blocks from the Beach/Park, holiday rental in Long Island

Sleek Condo w/ a Private Patio - Less than Two Blocks from the Beach/Park

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW LISTING ☼ Unique Oceanfront Home, holiday rental in Long Island

NEW LISTING ☼ Unique Oceanfront Home

2 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!!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Modern Apartment Two Blocks from Willard Beach in South Portland, holiday rental in Long Island

Modern Apartment Two Blocks from Willard Beach in South Portland

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Falmouth Waterfront Carriage House Apt, holiday rental in Long Island

Falmouth Waterfront Carriage House Apt

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable Portland getaway on the Eastern Promenade, holiday rental in Long Island

Adorable Portland getaway on the Eastern Promenade

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Polished, Modern Condo w/ a Balcony - Walk to Eastern Promenade & Casco Bay!, holiday rental in Long Island

Polished, Modern Condo w/ a Balcony - Walk to Eastern Promenade & Casco Bay!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautifully decorated executive home steps from a private beach, holiday rental in Long Island

Beautifully decorated executive home steps from a private beach

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Sleek & Newly-Renovated Third-Floor Condo w/ Amazing Water Views - Walk to Bay!, holiday rental in Long Island

Sleek & Newly-Renovated Third-Floor Condo w/ Amazing Water Views - Walk to Bay!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fresh East End Apartment Walkable to Downtown Portland, holiday rental in Long Island

Fresh East End Apartment Walkable to Downtown Portland

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Island Cottage, 5BR, holiday rental in Long Island

Historic Island Cottage, 5BR

5 bedrooms
3 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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Art Filled East End Home a short walk to waterfront, restaurants and shops, holiday rental in Long Island

Art Filled East End Home a short walk to waterfront, restaurants and shops

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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DIRECT OCEANFRONT Perfect location, holiday rental in Long Island

DIRECT OCEANFRONT Perfect location

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Portland B&B room - steps from Eastern Prom and beach and close to town too!, holiday rental in Long Island

Portland B&B room - steps from Eastern Prom and beach and close to town too!

1 bedroom
1 bathroom
Sleeps 4
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!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A charming, seaside cottage ~ Falmouth Foreside, holiday rental in Long Island

A charming, seaside cottage ~ Falmouth Foreside

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Waterfront House with Hot Tub, holiday rental in Long Island

Stunning Waterfront House with Hot Tub

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Sunset Cottage, Family-Friendly Oasis, holiday rental in Long Island

Sunset Cottage, Family-Friendly Oasis

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!, holiday rental in Long Island

WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!

3 bedrooms
2 bathrooms
Sleeps 9
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.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Adorable Peaks Island Cottage, holiday rental in Long Island

Adorable Peaks Island Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Evergreen cottage 5' from the water, holiday rental in Long Island

Evergreen cottage 5' from the water

5 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Willard Beach Get Away - Dog Friendly, holiday rental in Long Island

Willard Beach Get Away - Dog Friendly

0 bedrooms
1 bathroom
Sleeps 3
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

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oceanside escape � perfect family getaway!, holiday rental in Long Island

Oceanside escape � perfect family getaway!

3 bedrooms
2 bathrooms
Sleeps 5
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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 3-Bed, Walk to Beach n Bars, holiday rental in Long Island

Spacious 3-Bed, Walk to Beach n Bars

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Portland Area Cottage w/OCEAN VIEWS ~ pet friendly, holiday rental in Long Island

Portland Area Cottage w/OCEAN VIEWS ~ pet friendly

3 bedrooms
1 bathroom
Sleeps 6
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

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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WILLARD BEACH:  Stunning newly RENOVATED HOUSE!   4 Mins to DT Portland., holiday rental in Long Island

WILLARD BEACH: Stunning newly RENOVATED HOUSE! 4 Mins to DT Portland.

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining, holiday rental in Long Island

New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW: Stunningly Renovated Beach House with OCEAN VIEWS-steps to beach.  Pets OK!, holiday rental in Long Island

NEW: Stunningly Renovated Beach House with OCEAN VIEWS-steps to beach. Pets OK!

4 bedrooms
3 bathrooms
Sleeps 10
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

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Authentic Coastal Maine Cottage Living, holiday rental in Long Island

Authentic Coastal Maine Cottage Living

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Casco Bay Sunrise Vista, holiday rental in Long Island

Casco Bay Sunrise Vista

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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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

3 bedrooms
2 bathrooms
Sleeps 6
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

6 bedrooms
4 bathrooms
Sleeps 13
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

6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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