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Shelter Island Villas

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

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!, holiday rental in Shelter Island
Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!, holiday rental in Shelter Island
Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!, holiday rental in Shelter Island

Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Charming, Renovated Island Cottage - Shelter Island License #:  ********, holiday rental in Shelter Island
Charming, Renovated Island Cottage - Shelter Island License #:  ********, holiday rental in Shelter Island
Charming, Renovated Island Cottage - Shelter Island License #:  ********, holiday rental in Shelter Island

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

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

Beautiful, Waterfront Home With Dock And Heated Gunite Pool!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Stunning Shelter Island Estate, holiday rental in Shelter Island
Stunning Shelter Island Estate, holiday rental in Shelter Island
Stunning Shelter Island Estate, holiday rental in Shelter Island

Stunning Shelter Island Estate

Holiday Rental House
8 bedrooms
8 bathrooms
Sleeps 14
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Relaxing Getaway in the Heart of Shelter Island - great for families and couples, holiday rental in Shelter Island
Relaxing Getaway in the Heart of Shelter Island - great for families and couples, holiday rental in Shelter Island
Relaxing Getaway in the Heart of Shelter Island - great for families and couples, holiday rental in Shelter Island

Relaxing Getaway in the Heart of Shelter Island - great for families and couples

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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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, holiday rental in Shelter Island
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Shelter Island Waterfront House With Dock And Private Beach, holiday rental in Shelter Island
Shelter Island Waterfront House With Dock And Private Beach, holiday rental in Shelter Island
Shelter Island Waterfront House With Dock And Private Beach, holiday rental in Shelter Island

Shelter Island Waterfront House With Dock And Private Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Private Hamptons Cottage, holiday rental in Shelter Island
Private Hamptons Cottage, holiday rental in Shelter Island
Private Hamptons Cottage, holiday rental in Shelter Island

Private Hamptons Cottage

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!

Holiday Rental House
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., holiday rental in Shelter Island
Beautiful Secluded Family Home on Shelter Island., holiday rental in Shelter Island

Beautiful Secluded Family Home on Shelter Island.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Stylish, Country 4 BR  Retreat August Preferable, holiday rental in Shelter Island
Stylish, Country 4 BR  Retreat August Preferable, holiday rental in Shelter Island
Stylish, Country 4 BR  Retreat August Preferable, holiday rental in Shelter Island

Stylish, Country 4 BR Retreat August Preferable

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
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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, holiday rental in Shelter Island
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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach, holiday rental in Shelter Island
Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach, holiday rental in Shelter Island
Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach, holiday rental in Shelter Island

Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
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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;..., holiday rental in Shelter Island
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;...

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

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
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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., holiday rental in Shelter Island
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.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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Water Views, Renovated Home with Heated Gunite Pool, holiday rental in Shelter Island
Water Views, Renovated Home with Heated Gunite Pool, holiday rental in Shelter Island
Water Views, Renovated Home with Heated Gunite Pool, holiday rental in Shelter Island

Water Views, Renovated Home with Heated Gunite Pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Charming Shelter Island Oasis, holiday rental in Shelter Island
Charming Shelter Island Oasis, holiday rental in Shelter Island
Charming Shelter Island Oasis, holiday rental in Shelter Island

Charming Shelter Island Oasis

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
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Shelter Island Waterfront Home!, holiday rental in Shelter Island
Shelter Island Waterfront Home!, holiday rental in Shelter Island
Shelter Island Waterfront Home!, holiday rental in Shelter Island

Shelter Island Waterfront Home!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Spacious beach house with stunning water views, holiday rental in Shelter Island
Spacious beach house with stunning water views, holiday rental in Shelter Island
Spacious beach house with stunning water views, holiday rental in Shelter Island

Spacious beach house with stunning water views

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
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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, holiday rental in Shelter Island
Mid-century on idyllic pasture like setting with pond, holiday rental in Shelter Island

Mid-century on idyllic pasture like setting with pond

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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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..., holiday rental in Shelter Island
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...

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Family friendly home near beach with wonderful deck!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
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New Listing: Full waterviews, steps to the beach, kayaks available, holiday rental in Shelter Island
New Listing: Full waterviews, steps to the beach, kayaks available, holiday rental in Shelter Island
New Listing: Full waterviews, steps to the beach, kayaks available, holiday rental in Shelter Island

New Listing: Full waterviews, steps to the beach, kayaks available

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home W/Private Beach And Lots Of Room To Swim, Play, And Relax, holiday rental in Shelter Island
Waterfront Home W/Private Beach And Lots Of Room To Swim, Play, And Relax, holiday rental in Shelter Island
Waterfront Home W/Private Beach And Lots Of Room To Swim, Play, And Relax, holiday rental in Shelter Island

Waterfront Home W/Private Beach And Lots Of Room To Swim, Play, And Relax

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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NEW LISTING: Farmhouse renovated w/ Convenience + Comfort, Stylish and..., holiday rental in Shelter Island
NEW LISTING: Farmhouse renovated w/ Convenience + Comfort, Stylish and..., holiday rental in Shelter Island
NEW LISTING: Farmhouse renovated w/ Convenience + Comfort, Stylish and..., holiday rental in Shelter Island

NEW LISTING: Farmhouse renovated w/ Convenience + Comfort, Stylish and...

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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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, holiday rental in Shelter Island
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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The Ultimate Beach House, holiday rental in Shelter Island
The Ultimate Beach House, holiday rental in Shelter Island
The Ultimate Beach House, holiday rental in Shelter Island

The Ultimate Beach House

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 15
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Shelter Island, Waterfront, Lazy Days With Stunning Views, holiday rental in Shelter Island
Shelter Island, Waterfront, Lazy Days With Stunning Views, holiday rental in Shelter Island
Shelter Island, Waterfront, Lazy Days With Stunning Views, holiday rental in Shelter Island

Shelter Island, Waterfront, Lazy Days With Stunning Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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!!, holiday rental in Shelter Island
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!!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Gorgeous, tranquil 9000 Sq Ft home on Dering Harbor

Holiday Rental House
6 bedrooms
10 bathrooms
Sleeps 12
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Modern and Efficient Beachfront Paradise, holiday rental in Shelter Island
Modern and Efficient Beachfront Paradise, holiday rental in Shelter Island
Modern and Efficient Beachfront Paradise, holiday rental in Shelter Island

Modern and Efficient Beachfront Paradise

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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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, holiday rental in Shelter Island
Summer Sun and Family Fun in Shelter Island, holiday rental in Shelter Island

Summer Sun and Family Fun in Shelter Island

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Waterfront Charmer on idyllic Shelter Island, holiday rental in Shelter Island
Waterfront Charmer on idyllic Shelter Island, holiday rental in Shelter Island
Waterfront Charmer on idyllic Shelter Island, holiday rental in Shelter Island

Waterfront Charmer on idyllic Shelter Island

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Payment Protection
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, holiday rental in Shelter Island
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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Charming, Historic Cottage, holiday rental in Shelter Island
Charming, Historic Cottage, holiday rental in Shelter Island
Charming, Historic Cottage, holiday rental in Shelter Island

Charming, Historic Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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NEW LISTING: Spacious living, Perfect Getaway, Bright Open Floor Plan, Amazing L, holiday rental in Shelter Island
NEW LISTING: Spacious living, Perfect Getaway, Bright Open Floor Plan, Amazing L, holiday rental in Shelter Island
NEW LISTING: Spacious living, Perfect Getaway, Bright Open Floor Plan, Amazing L, holiday rental in Shelter Island

NEW LISTING: Spacious living, Perfect Getaway, Bright Open Floor Plan, Amazing L

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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New Listing: Renovated, Victorian-Style Home in Sag Harbor, Al Fresco..., holiday rental in Shelter Island
New Listing: Renovated, Victorian-Style Home in Sag Harbor, Al Fresco..., holiday rental in Shelter Island
New Listing: Renovated, Victorian-Style Home in Sag Harbor, Al Fresco..., holiday rental in Shelter Island

New Listing: Renovated, Victorian-Style Home in Sag Harbor, Al Fresco...

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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SHELTER ISLAND: light-filled renovated farmhouse short walk to town and harbor, holiday rental in Shelter Island
SHELTER ISLAND: light-filled renovated farmhouse short walk to town and harbor, holiday rental in Shelter Island
SHELTER ISLAND: light-filled renovated farmhouse short walk to town and harbor, holiday rental in Shelter Island

SHELTER ISLAND: light-filled renovated farmhouse short walk to town and harbor

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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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 &..., holiday rental in Shelter Island
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 &...

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Private wooded summer house 5 minute walk to Wades Beach, holiday rental in Shelter Island
Private wooded summer house 5 minute walk to Wades Beach, holiday rental in Shelter Island
Private wooded summer house 5 minute walk to Wades Beach, holiday rental in Shelter Island

Private wooded summer house 5 minute walk to Wades Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!, holiday rental in Shelter Island
This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!, holiday rental in Shelter Island
This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!, holiday rental in Shelter Island

This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 16
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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, holiday rental in Shelter Island
Bright and Airy West Neck Bay Shingle Style House, holiday rental in Shelter Island

Bright and Airy West Neck Bay Shingle Style House

Holiday Rental 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, holiday rental in Shelter Island
Lovely property near beaches and amenities, holiday rental in Shelter Island

Lovely property near beaches and amenities

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Charming Shelter Island Home, holiday rental in Shelter Island
Charming Shelter Island Home, holiday rental in Shelter Island
Charming Shelter Island Home, holiday rental in Shelter Island

Charming Shelter Island Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Waterfront Charmer on idyllic Shelter Island for summer rental, holiday rental in Shelter Island
Waterfront Charmer on idyllic Shelter Island for summer rental, holiday rental in Shelter Island
Waterfront Charmer on idyllic Shelter Island for summer rental, holiday rental in Shelter Island

Waterfront Charmer on idyllic Shelter Island for summer rental

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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Perfect family getaway on beautiful Shelter Island!, holiday rental in Shelter Island
Perfect family getaway on beautiful Shelter Island!, holiday rental in Shelter Island
Perfect family getaway on beautiful Shelter Island!, holiday rental in Shelter Island

Perfect family getaway on beautiful Shelter Island!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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, holiday rental in Shelter Island
Pristine renovated home within minutes of West Neck harbor, holiday rental in Shelter Island

Pristine renovated home within minutes of West Neck harbor

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Renovated Beach House with Pool, Waterviews, Central Air, and Private Beach, holiday rental in Shelter Island
Renovated Beach House with Pool, Waterviews, Central Air, and Private Beach, holiday rental in Shelter Island
Renovated Beach House with Pool, Waterviews, Central Air, and Private Beach, holiday rental in Shelter Island

Renovated Beach House with Pool, Waterviews, Central Air, and Private Beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Frequently Asked Questions about Shelter Island