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Shelter Island
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Apartments and Vacation Rentals in Shelter Island, NY
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Kid friendly (30)
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37 rentals
in Shelter Island.
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Newly renovated! Quiet, private, short walk to the beach.
56 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Charming A-Frame Home On Private Quiet Road
40 reviews
3 bedrooms
1 bathroom
Sleeps 6
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Beautiful, Waterfront Home With Dock And Heated Gunite Pool!
18 reviews
4 bedrooms
3 bathrooms
Sleeps 10
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Charming, Renovated Island Cottage - Shelter Island License #: ********
24 reviews
2 bedrooms
1 bathroom
Sleeps 4
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Perfect Family Summer Vacation Home Close to beach 18x42 pool
23 reviews
3 bedrooms
3 bathrooms
Sleeps 6
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Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
12 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Secluded Family Home on Shelter Island.
13 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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NEW LISTING: LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES;...
7 reviews
5 bedrooms
7 bathrooms
Sleeps 10
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Private Hamptons Cottage
5 reviews
5 bedrooms
2 bathrooms
Sleeps 10
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Shelter Island Escape Awaits
8 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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Shelter Island Waterfront Home!
4 reviews
5 bedrooms
4 bathrooms
Sleeps 10
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Charming Shelter Island Oasis
3 reviews
4 bedrooms
4 bathrooms
Sleeps 5
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Mid-century on idyllic pasture like setting with pond
3 reviews
3 bedrooms
2 bathrooms
Sleeps 5
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Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape.
2 reviews
4 bedrooms
3 bathrooms
Sleeps 7
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Contemporary Home on Quiet Country Road/Walk to beach and Fresh Pond
2 reviews
3 bedrooms
2 bathrooms
Sleeps 7
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Waterfront Charmer on idyllic Shelter Island
3 bedrooms
3 bathrooms
Sleeps 8
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Stunning Waterfront Estate House with 270 degree sea views on 7 private acres
1 review
4 bedrooms
4 bathrooms
Sleeps 2
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Gorgeous, tranquil 9000 Sq Ft home on Dering Harbor
1 review
6 bedrooms
10 bathrooms
Sleeps 12
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New Listing: Beautiful Waterview 4-Bedroom Home, Newly Renovated with Huge...
1 review
4 bedrooms
3 bathrooms
Sleeps 8
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Summer Sun and Family Fun in Shelter Island
4 bedrooms
3 bathrooms
Sleeps 8
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The Ultimate Beach House
7 bedrooms
5 bathrooms
Sleeps 15
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Luxurious 'Shelter Island Hideaway' w/ Pool!
4 bedrooms
4 bathrooms
Sleeps 10
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Hilo Shores, bay access, air conditioned , rec room, spotless , family ready!!
3 bedrooms
3 bathrooms
Sleeps 6
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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 &...
3 bedrooms
3 bathrooms
Sleeps 8
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New Listing: Technicolor Paradise, Architectural Masterpiece Amidst...
4 bedrooms
3 bathrooms
Sleeps 6
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Family friendly home near beach with wonderful deck!
4 bedrooms
2 bathrooms
Sleeps 7
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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
3 bedrooms
2 bathrooms
Sleeps 6
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A FAMILY’S DREAM & THE DEFINITION OF SERENITY
4 bedrooms
3 bathrooms
Sleeps 10
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Cozy Cottage for 2 - great for couples/singles - in the heart of Shelter Island!
1 bedroom
1 bathroom
Sleeps 2
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New Renovation Waterfront House With Dock. Best Location In Shelter Island
3 bedrooms
3 bathrooms
Sleeps 8
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Pristine renovated home within minutes of West Neck harbor
3 bedrooms
3 bathrooms
Sleeps 6
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Stunning Shelter Island Estate
8 bedrooms
8 bathrooms
Sleeps 14
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Chic Shelter Island Home, Pool and Gardens
3 bedrooms
2 bathrooms
Sleeps 6
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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
2 bedrooms
3 bathrooms
Sleeps 7
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1
Frequently Asked Questions about Shelter Island
Do any vacation rentals in Shelter Island have a pool?
Yes, here are some popular vacation rentals in Shelter Island that have a pool:
The Ultimate Beach House
Beautiful, Waterfront Home With Dock And Heated Gunite Pool!
Perfect Family Summer Vacation Home Close to beach 18x42 pool
See all vacation rentals with a pool in Shelter Island on Tripadvisor
Do any vacation rentals in Shelter Island have internet access?
Yes, here are some popular vacation rentals in Shelter Island that have internet access:
Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape.
Summer Sun and Family Fun in Shelter Island
Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
See all vacation rentals in Shelter Island on Tripadvisor
What are the best pet friendly rentals in Shelter Island?
The best pet friendly rentals in Shelter Island are:
Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape.
Summer Sun and Family Fun in Shelter Island
Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
See all pet friendly vacation rentals in Shelter Island on Tripadvisor
What are some great rentals in Shelter Island that are kid friendly?
Some of the most popular kid friendly rentals in Shelter Island are:
Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape.
Summer Sun and Family Fun in Shelter Island
Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
See all kid friendly vacation rentals in Shelter Island on Tripadvisor