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Shelter Island Holiday Rentals

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35 rentals in Shelter Island.
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Newly renovated! Quiet, private, short walk to the beach., holiday rental in Shelter Island

Newly renovated! Quiet, private, short walk to the beach.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming  A-Frame Home On Private Quiet Road, holiday rental in Shelter Island

Charming A-Frame Home On Private Quiet Road

3 bedrooms
1 bathroom
Sleeps 6
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Charming, Renovated Island Cottage - Shelter Island License #:  ********, holiday rental in Shelter Island

Charming, Renovated Island Cottage - Shelter Island License #: ********

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful, Waterfront Home With Dock And Heated Gunite Pool!, holiday rental in Shelter Island

Beautiful, Waterfront Home With Dock And Heated Gunite Pool!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Perfect Family Summer Vacation Home Close to beach 18x42 pool, holiday rental in Shelter Island

Perfect Family Summer Vacation Home Close to beach 18x42 pool

3 bedrooms
3 bathrooms
Sleeps 6
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Stunning Shelter Island Estate, holiday rental in Shelter Island

Stunning Shelter Island Estate

8 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!, holiday rental in Shelter Island

Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!

4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Secluded Family Home on Shelter Island., holiday rental in Shelter Island

Beautiful Secluded Family Home on Shelter Island.

4 bedrooms
3 bathrooms
Sleeps 8
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Private Hamptons Cottage, holiday rental in Shelter Island

Private Hamptons Cottage

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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NEW LISTING: LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES;..., holiday rental in Shelter Island

NEW LISTING: LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES;...

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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New Listing: Technicolor Paradise, Architectural Masterpiece Amidst..., holiday rental in Shelter Island

New Listing: Technicolor Paradise, Architectural Masterpiece Amidst...

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Waterfront Estate House with 270 degree sea views on 7 private acres, holiday rental in Shelter Island

Stunning Waterfront Estate House with 270 degree sea views on 7 private acres

4 bedrooms
4 bathrooms
Sleeps 2
Match: Sleeps
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Shelter Island Escape Awaits, holiday rental in Shelter Island

Shelter Island Escape Awaits

4 bedrooms
3 bathrooms
Sleeps 8
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Views-Views-Views of beautiful Peconic Bay.  Tastefully renovated 1929 Cape., holiday rental in Shelter Island

Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape.

4 bedrooms
3 bathrooms
Sleeps 7
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Shelter Island Waterfront Home!, holiday rental in Shelter Island

Shelter Island Waterfront Home!

5 bedrooms
4 bathrooms
Sleeps 10
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Charming Shelter Island Oasis, holiday rental in Shelter Island

Charming Shelter Island Oasis

4 bedrooms
4 bathrooms
Sleeps 5
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Mid-century on idyllic pasture like setting with pond, holiday rental in Shelter Island

Mid-century on idyllic pasture like setting with pond

3 bedrooms
2 bathrooms
Sleeps 5
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Family friendly home near beach with wonderful deck!, holiday rental in Shelter Island

Family friendly home near beach with wonderful deck!

4 bedrooms
2 bathrooms
Sleeps 7
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Contemporary Home on Quiet Country Road/Walk to beach and Fresh Pond, holiday rental in Shelter Island

Contemporary Home on Quiet Country Road/Walk to beach and Fresh Pond

3 bedrooms
2 bathrooms
Sleeps 7
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Cozy Cottage for 2 - great for couples/singles - in the heart of Shelter Island!, holiday rental in Shelter Island

Cozy Cottage for 2 - great for couples/singles - in the heart of Shelter Island!

1 bedroom
1 bathroom
Sleeps 2
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Gorgeous, tranquil 9000 Sq Ft home on Dering Harbor, holiday rental in Shelter Island

Gorgeous, tranquil 9000 Sq Ft home on Dering Harbor

6 bedrooms
10 bathrooms
Sleeps 12
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New Listing: Beautiful Waterview 4-Bedroom Home, Newly Renovated with Huge..., holiday rental in Shelter Island

New Listing: Beautiful Waterview 4-Bedroom Home, Newly Renovated with Huge...

4 bedrooms
3 bathrooms
Sleeps 8
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Summer Sun and Family Fun in Shelter Island, holiday rental in Shelter Island

Summer Sun and Family Fun in Shelter Island

4 bedrooms
3 bathrooms
Sleeps 8
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The Ultimate Beach House, holiday rental in Shelter Island

The Ultimate Beach House

7 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Waterfront Charmer on idyllic Shelter Island, holiday rental in Shelter Island

Waterfront Charmer on idyllic Shelter Island

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hilo Shores, bay access, air conditioned ,  rec room, spotless , family ready!!, holiday rental in Shelter Island

Hilo Shores, bay access, air conditioned , rec room, spotless , family ready!!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming 4 Bed/2.5 Bath Cottage In Historic Shelter Island, Walk To Ferry, holiday rental in Shelter Island

Charming 4 Bed/2.5 Bath Cottage In Historic Shelter Island, Walk To Ferry

4 bedrooms
2 bathrooms
Sleeps 8
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New Listing: Rustic Chic Designer Home on Dering Harbor, Private Dock &..., holiday rental in Shelter Island

New Listing: Rustic Chic Designer Home on Dering Harbor, Private Dock &...

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bright and Airy West Neck Bay Shingle Style House, holiday rental in Shelter Island

Bright and Airy West Neck Bay Shingle Style House

3 bedrooms
3 bathrooms
Sleeps 10
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Lovely property near beaches and amenities, holiday rental in Shelter Island

Lovely property near beaches and amenities

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A FAMILY’S DREAM & THE DEFINITION OF SERENITY, holiday rental in Shelter Island

A FAMILY’S DREAM & THE DEFINITION OF SERENITY

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Pristine renovated home within minutes of West Neck harbor, holiday rental in Shelter Island

Pristine renovated home within minutes of West Neck harbor

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Chic Shelter Island Home, Pool and Gardens, holiday rental in Shelter Island

Chic Shelter Island Home, Pool and Gardens

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious house next to the beach, Ferry and Eateries., holiday rental in Shelter Island

Spacious house next to the beach, Ferry and Eateries.

6 bedrooms
5 bathrooms
Sleeps 11
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WATERFRONT with Private Beach Boat Dock and Launch Ramp Sleeps 7, holiday rental in Shelter Island

WATERFRONT with Private Beach Boat Dock and Launch Ramp Sleeps 7

2 bedrooms
3 bathrooms
Sleeps 7
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