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Long Island Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
47 rentals in Long Island.
Heartrock on Long Island, holiday rental in Long Island
Heartrock on Long Island, holiday rental in Long Island
Heartrock on Long Island, holiday rental in Long Island

Heartrock on Long Island

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Updated Long Island Maine Cottage, holiday rental in Long Island
Updated Long Island Maine Cottage, holiday rental in Long Island
Updated Long Island Maine Cottage, holiday rental in Long Island

Updated Long Island Maine Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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 5
Match: Sleeps
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Private Oceanfront Island Estate, holiday rental in Long Island
Private Oceanfront Island Estate, holiday rental in Long Island
Private Oceanfront Island Estate, holiday rental in Long Island

Private Oceanfront Island Estate

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 20
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!, 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
Match: Sleeps
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Experienced 5 Star Host! 8 bed/6 bath, Incredible porches, a short walk to, holiday rental in Long Island
Experienced 5 Star Host! 8 bed/6 bath, Incredible porches, a short walk to, holiday rental in Long Island
Experienced 5 Star Host! 8 bed/6 bath, Incredible porches, a short walk to, holiday rental in Long Island

Experienced 5 Star Host! 8 bed/6 bath, Incredible porches, a short walk to

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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The following properties within 20 miles of Long Island match all your filters:
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
Match: Sleeps
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Large, light filled 4 bedroom house - walk to ocean and ferry, holiday rental in Long Island
Large, light filled 4 bedroom house - walk to ocean and ferry, holiday rental in Long Island
Large, light filled 4 bedroom house - walk to ocean and ferry, holiday rental in Long Island

Large, light filled 4 bedroom house - walk to ocean and ferry

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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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
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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Classic Island Cottage, holiday rental in Long Island
Classic Island Cottage, holiday rental in Long Island
Classic Island Cottage, holiday rental in Long Island

Classic Island Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Long Island
Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Long Island
Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Long Island

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Cozy Historic Home on Great Diamond Island, holiday rental in Long Island
Cozy Historic Home on Great Diamond Island, holiday rental in Long Island
Cozy Historic Home on Great Diamond Island, holiday rental in Long Island

Cozy Historic Home on Great Diamond Island

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury King Room with Parlor and Balcony, holiday rental in Long Island
Luxury King Room with Parlor and Balcony, holiday rental in Long Island
Luxury King Room with Parlor and Balcony, holiday rental in Long Island

Luxury King Room with Parlor and Balcony

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Beach House Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Long Island
The Beach House Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Long Island
The Beach House Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Long Island

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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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 2
Match: Sleeps
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King Suite with Kitchenette & Balcony on Great Diamond Island, holiday rental in Long Island
King Suite with Kitchenette & Balcony on Great Diamond Island, holiday rental in Long Island
King Suite with Kitchenette & Balcony on Great Diamond Island, holiday rental in Long Island

King Suite with Kitchenette & Balcony on Great Diamond Island

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Sweet Island Cottage- 3 minute walk to beach, holiday rental in Long Island
Sweet Island Cottage- 3 minute walk to beach, holiday rental in Long Island
Sweet Island Cottage- 3 minute walk to beach, holiday rental in Long Island

Sweet Island Cottage- 3 minute walk to beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Welcome to Happy Place on Peaks Island, holiday rental in Long Island
Welcome to Happy Place on Peaks Island, holiday rental in Long Island
Welcome to Happy Place on Peaks Island, holiday rental in Long Island

Welcome to Happy Place on Peaks Island

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cute 2+ Bedroom Cottage, holiday rental in Long Island
Cute 2+ Bedroom Cottage, holiday rental in Long Island
Cute 2+ Bedroom Cottage, holiday rental in Long Island

Cute 2+ Bedroom Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New Ocean-front, Peaks Island, Portland home, Beaches,, holiday rental in Long Island
New Ocean-front, Peaks Island, Portland home, Beaches,, holiday rental in Long Island
New Ocean-front, Peaks Island, Portland home, Beaches,, holiday rental in Long Island

New Ocean-front, Peaks Island, Portland home, Beaches,

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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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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Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side, holiday rental in Long Island
Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side, holiday rental in Long Island
Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side, holiday rental in Long Island

Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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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Historic Bakery House on Great Diamond Island with Lots of Charm, holiday rental in Long Island
Historic Bakery House on Great Diamond Island with Lots of Charm, holiday rental in Long Island
Historic Bakery House on Great Diamond Island with Lots of Charm, holiday rental in Long Island

Historic Bakery House on Great Diamond Island with Lots of Charm

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean House: Stunning Oceanfront Views, Spectacular Sunrises Peaks Island, Maine, holiday rental in Long Island
Ocean House: Stunning Oceanfront Views, Spectacular Sunrises Peaks Island, Maine, holiday rental in Long Island
Ocean House: Stunning Oceanfront Views, Spectacular Sunrises Peaks Island, Maine, holiday rental in Long Island

Ocean House: Stunning Oceanfront Views, Spectacular Sunrises Peaks Island, Maine

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Long Island
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Long Island
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Long Island

NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Classic turn of the century Maine cottage, holiday rental in Long Island
Classic turn of the century Maine cottage, holiday rental in Long Island
Classic turn of the century Maine cottage, holiday rental in Long Island

Classic turn of the century Maine cottage

Holiday Rental House
4 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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Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!, holiday rental in Long Island
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!, holiday rental in Long Island
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!, holiday rental in Long Island

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Wonderful Summer Cottage on Great Diamond Island, holiday rental in Long Island
Wonderful Summer Cottage on Great Diamond Island, holiday rental in Long Island
Wonderful Summer Cottage on Great Diamond Island, holiday rental in Long Island

Wonderful Summer Cottage on Great Diamond Island

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Knit 1, Purl 2: Fabulous Turn Of The Century Cottage, Peaks Island, ME, holiday rental in Long Island
Knit 1, Purl 2: Fabulous Turn Of The Century Cottage, Peaks Island, ME, holiday rental in Long Island
Knit 1, Purl 2: Fabulous Turn Of The Century Cottage, Peaks Island, ME, holiday rental in Long Island

Knit 1, Purl 2: Fabulous Turn Of The Century Cottage, Peaks Island, ME

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious island home on the water, 30 minute ferry ride from Portland Maine, holiday rental in Long Island
Luxurious island home on the water, 30 minute ferry ride from Portland Maine, holiday rental in Long Island
Luxurious island home on the water, 30 minute ferry ride from Portland Maine, holiday rental in Long Island

Luxurious island home on the water, 30 minute ferry ride from Portland Maine

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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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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
6 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic Turn of the Century Island Summer Cottage, holiday rental in Long Island
Classic Turn of the Century Island Summer Cottage, holiday rental in Long Island
Classic Turn of the Century Island Summer Cottage, holiday rental in Long Island

Classic Turn of the Century Island Summer Cottage

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Island Cottage, Portland, ME, Sleeps 6-8, Walk to ferry, beach, restaurants., holiday rental in Long Island
Island Cottage, Portland, ME, Sleeps 6-8, Walk to ferry, beach, restaurants., holiday rental in Long Island
Island Cottage, Portland, ME, Sleeps 6-8, Walk to ferry, beach, restaurants., holiday rental in Long Island

Island Cottage, Portland, ME, Sleeps 6-8, Walk to ferry, beach, restaurants.

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Contemporary Home with Historic Charm, holiday rental in Long Island
Contemporary Home with Historic Charm, holiday rental in Long Island
Contemporary Home with Historic Charm, holiday rental in Long Island

Contemporary Home with Historic Charm

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Dwelling Place Su, holiday rental in Long Island
The Dwelling Place Su, holiday rental in Long Island
The Dwelling Place Su, holiday rental in Long Island

The Dwelling Place Su

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New Listing - Private Oceanfront Property on Peaks Island, Maine - Sleeps 10, holiday rental in Long Island
New Listing - Private Oceanfront Property on Peaks Island, Maine - Sleeps 10, holiday rental in Long Island
New Listing - Private Oceanfront Property on Peaks Island, Maine - Sleeps 10, holiday rental in Long Island

New Listing - Private Oceanfront Property on Peaks Island, Maine - Sleeps 10

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Dairy House Summa, holiday rental in Long Island
The Dairy House Summa, holiday rental in Long Island
The Dairy House Summa, holiday rental in Long Island

The Dairy House Summa

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront with private beach., holiday rental in Long Island
Waterfront with private beach., holiday rental in Long Island
Waterfront with private beach., holiday rental in Long Island

Waterfront with private beach.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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RubySayl Summary:Sim, holiday rental in Long Island
RubySayl Summary:Sim, holiday rental in Long Island
RubySayl Summary:Sim, holiday rental in Long Island

RubySayl Summary:Sim

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sea Glass - Peaks Island oceanfront cottage with stunning views for 7 people!, holiday rental in Long Island
Sea Glass - Peaks Island oceanfront cottage with stunning views for 7 people!, holiday rental in Long Island
Sea Glass - Peaks Island oceanfront cottage with stunning views for 7 people!, holiday rental in Long Island

Sea Glass - Peaks Island oceanfront cottage with stunning views for 7 people!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Sweet Thing Summary:, holiday rental in Long Island
Sweet Thing Summary:, holiday rental in Long Island
Sweet Thing Summary:, holiday rental in Long Island

Sweet Thing Summary:

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-47 of 47
Frequently Asked Questions about Long Island