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Middle Island Holiday Rentals

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49 rentals in Middle Island.
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Secluded Long Island Lakefront Cabin w/Deck+Grill!, holiday rental in Middle Island

Secluded Long Island Lakefront Cabin w/Deck+Grill!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Sunny 1 Bedroom Apartment in Bellport, holiday rental in Middle Island

Beautiful Sunny 1 Bedroom Apartment in Bellport

1 bedroom
1 bathroom
Sleeps 2
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Waterfront & private beach  Scandinavian style house near Bellport, NY, holiday rental in Middle Island

Waterfront & private beach Scandinavian style house near Bellport, NY

3 bedrooms
2 bathrooms
Sleeps 6
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Airy Cottage in Bellport Village, holiday rental in Middle Island

Airy Cottage in Bellport Village

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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WATERFRONT BEACH HOUSE - SOUND BEACH, holiday rental in Middle Island

WATERFRONT BEACH HOUSE - SOUND BEACH

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Family Friendly, short walk to water and Tidal pooling, holiday rental in Middle Island

Family Friendly, short walk to water and Tidal pooling

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Water Views from this Immaculate, Sunny Home in Bellport Village with Pool., holiday rental in Middle Island

Water Views from this Immaculate, Sunny Home in Bellport Village with Pool.

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Summer retreat with spectacular view of Long Island Sound, holiday rental in Middle Island

Summer retreat with spectacular view of Long Island Sound

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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2 Bedroom Apartment with Access to LI Sound, holiday rental in Middle Island

2 Bedroom Apartment with Access to LI Sound

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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waterview house. rocky point. long island.New york, holiday rental in Middle Island

waterview house. rocky point. long island.New york

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Luxury Beach House w Panoramic Views 1.5hrs NYC Your own Private Beach!, holiday rental in Middle Island

Luxury Beach House w Panoramic Views 1.5hrs NYC Your own Private Beach!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Historic House Overlooking the Long Island Sound, holiday rental in Middle Island

Historic House Overlooking the Long Island Sound

9 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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Designer retreat with pool in Bellport Village, holiday rental in Middle Island

Designer retreat with pool in Bellport Village

3 bedrooms
2 bathrooms
Sleeps 8
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Sunny and Bright Home in Central Location!, holiday rental in Middle Island

Sunny and Bright Home in Central Location!

3 bedrooms
2 bathrooms
Sleeps 6
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Lodge/ Bunk House with Access to LI Sound, holiday rental in Middle Island

Lodge/ Bunk House with Access to LI Sound

4 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Casa Playa - Secluded Oasis on the LI Northfork - Monthly Rentals Only!, holiday rental in Middle Island

Casa Playa - Secluded Oasis on the LI Northfork - Monthly Rentals Only!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Soundview Lodge- Overlooking Long Island Sound, holiday rental in Middle Island

Soundview Lodge- Overlooking Long Island Sound

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Queen Vic Luxury Beach House Vineyards Farms Hamptons Your own Private Beach!, holiday rental in Middle Island

Queen Vic Luxury Beach House Vineyards Farms Hamptons Your own Private Beach!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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SECLUDED & INTIMATE: Immaculate Cottage at start of the North Fork Wine Country, holiday rental in Middle Island

SECLUDED & INTIMATE: Immaculate Cottage at start of the North Fork Wine Country

2 bedrooms
2 bathrooms
Sleeps 4
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Romantic Beach House Vineyards Farms North Fork Your own Private Beach!, holiday rental in Middle Island

Romantic Beach House Vineyards Farms North Fork Your own Private Beach!

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Luxurious Mermaid Inn Beach House Kayaks SUP jacuzzi sleeps 12, holiday rental in Middle Island

Luxurious Mermaid Inn Beach House Kayaks SUP jacuzzi sleeps 12

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Waters edge Beach House VIEWS North Fork Hamptons Your Private Beach Jacuzzi, holiday rental in Middle Island

Waters edge Beach House VIEWS North Fork Hamptons Your Private Beach Jacuzzi

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Beach Cottage Wineries, Shopping & the Hamptons, holiday rental in Middle Island

Luxury Beach Cottage Wineries, Shopping & the Hamptons

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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True beach House Once Upon A Tide Right on the Beach!, holiday rental in Middle Island

True beach House Once Upon A Tide Right on the Beach!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Glen Laurel on the Sound, holiday rental in Middle Island

Glen Laurel on the Sound

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Luxury Beach House Heart North Fork Wineries Hamptons Your own Private Beach!, holiday rental in Middle Island

Luxury Beach House Heart North Fork Wineries Hamptons Your own Private Beach!

1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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The Seaside Beach House North Fork Vineyards Hamptons, holiday rental in Middle Island

The Seaside Beach House North Fork Vineyards Hamptons

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Dunes Upscale Beach House Vineyards Farm Stands North Fork vineyards, holiday rental in Middle Island

The Dunes Upscale Beach House Vineyards Farm Stands North Fork vineyards

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury Beach House near Hamptons Vineyards walk to Restaurant 60 miles NYC, holiday rental in Middle Island

Luxury Beach House near Hamptons Vineyards walk to Restaurant 60 miles NYC

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Amazing Rocky Point Retreat Overlooking the Sound!, holiday rental in Middle Island

Amazing Rocky Point Retreat Overlooking the Sound!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach Cottage by the Sea Views private Steps to the private beach!, holiday rental in Middle Island

Beach Cottage by the Sea Views private Steps to the private beach!

4 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Frank Lloyd Wright Prairie Style Home on 4 Acres Wild Life Refuge, holiday rental in Middle Island

Frank Lloyd Wright Prairie Style Home on 4 Acres Wild Life Refuge

5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Studio bedroom livingroom combo with private bathroom and enterance, holiday rental in Middle Island

Studio bedroom livingroom combo with private bathroom and enterance

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cheaper Than a Hotel! Spacious Guest Suite in Medford, Long Island, holiday rental in Middle Island

Cheaper Than a Hotel! Spacious Guest Suite in Medford, Long Island

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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1 bedroom apartment apartment home away from home., holiday rental in Middle Island

1 bedroom apartment apartment home away from home.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bellport Village Summer Get Away, holiday rental in Middle Island

Bellport Village Summer Get Away

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Port Jefferson Coastal Paradise, holiday rental in Middle Island

Port Jefferson Coastal Paradise

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Hidden Gem North Fork Home w/ heated Pool & beach amenities Vineyards farms, holiday rental in Middle Island

Hidden Gem North Fork Home w/ heated Pool & beach amenities Vineyards farms

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bellport Village OBK, holiday rental in Middle Island

Bellport Village OBK

3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Blue Haven Brand New Beach house Panoramic Views Your own Private Beach!, holiday rental in Middle Island

Blue Haven Brand New Beach house Panoramic Views Your own Private Beach!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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North Fork Beach House steps to beach Farm Stands, Kayaks, avail all season, holiday rental in Middle Island

North Fork Beach House steps to beach Farm Stands, Kayaks, avail all season

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Summer By The Sea 5Br Beach house Kayaks/Paddle Highspeed Internet Vineyards, holiday rental in Middle Island

Summer By The Sea 5Br Beach house Kayaks/Paddle Highspeed Internet Vineyards

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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*VIEWS** Luxury Beach House overlooking the Long Island Sound **VIEWS**, holiday rental in Middle Island

*VIEWS** Luxury Beach House overlooking the Long Island Sound **VIEWS**

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Miller’s secret, holiday rental in Middle Island

Miller’s secret

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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3BR Sea Cliff Charming Beach Cottage Kayak Paddle, holiday rental in Middle Island

3BR Sea Cliff Charming Beach Cottage Kayak Paddle

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW! Rocky Point Escape w/ Grill - 1 Mi to Beach!, holiday rental in Middle Island

NEW! Rocky Point Escape w/ Grill - 1 Mi to Beach!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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NEW! Vivid Escape on Long Island - Walk to Beach!, holiday rental in Middle Island

NEW! Vivid Escape on Long Island - Walk to Beach!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Entire House near Smith Point Beach, holiday rental in Middle Island

Entire House near Smith Point Beach

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Upscale Mount Sinai Home ~ 2 Miles to Beach!, holiday rental in Middle Island

NEW! Upscale Mount Sinai Home ~ 2 Miles to Beach!

6 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Near Smith Point Beach.  Furnished private studio apartment., holiday rental in Middle Island

Near Smith Point Beach. Furnished private studio apartment.

1 bedroom
1 bathroom
Sleeps 1
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