Shelter Island, NY Vacation Rentals - Long Island, NY

Shelter Island, NY vacation rentals, browse Shelter Island, New York vacation home rentals and plan your next Long Island vacation on Shelter Island Long Island. Imagine relaxing on Shelter Island, NY vacationing by yourself, vacationing with your family or vacationing with friends, whatever your plans may be, make your next vacation a Shelter Island, Long Island vacation.

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Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Peaceful Shelter Island Getaway – Directly Across From Preserved Land, Two Balconies, Gravel Patio Area w/A Fire Pit.

Sleeps: 5
Bedrooms: 3
Bathrooms: 1
Pets Considered

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The Heights, NY

Shelter Island, Long Island Vacation Rentals

Renovated Victorian In The Heart Of It All, Bikes, Deck Overlooking A Private Pond, 15 Min Walk To Crescent Beach & Sunset Beach.

Sleeps: 8
Bedrooms: 3
Bathrooms: 3
No Pets

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Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Charming A-frame Home On Private Quiet Road, Beautiful Deck For Entertaining, Intimate Fire-Pit, Sun Drenched 3BD.

Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets

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The Heights, NY

Shelter Island, Long Island Vacation Rentals

Newly Renovated w/Pool, Hot Tub & Fireplace, Perfect Family Getaway, We Also Have Toys, Pool Toys & A Wii w/Lots Of Games.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets

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Menantic Creek, NY

Shelter Island, Long Island Vacation Rentals

Shelter Island Sun Filled Modern Waterfront Retreat! Spend Your Day On The Spacious Deck, On The Dock, Or On The Water.

Sleeps: 6
Bedrooms: 3
Bathrooms: 4
No Pets

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Silver Beach, NY

Shelter Island, Long Island Vacation Rentals

Relax In This Spacious, Light-Filled Vacation Home w/Pool In Silver Beach. Playset For Children, Your Very Own Zip Line For Hours Of Fun!

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets

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Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Perfect Family Summer Vacation Home Close To Beach, 18×42 Pool, Basement w/Air Hockey And Foosball, Large Outdoor Deck, Front & Side Porch.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
Pets Considered

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Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Walk To Sunset Beach: Perfect Family Getaway: Historic Colonial, Large Backyard For Family Activities, Quick Access To Beaches, Town  & Ferries.

Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets

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Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Shelter Island Waterfront House w/Dock And Private Beach, Complimentary Kayaks & Bicycles, Wraparound Deck & Garden Hammock.

Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets

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Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Farmhouse Nestled By Meadow, Gunite Saline Pool, Near Beaches & Centrally Located! Sun Porch, Patio Area With Outdoor Seating.

Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets

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Silver Beach, NY

Shelter Island, Long Island Vacation Rentals

Newly Renovated! Quiet, Private, Short Walk To The Beach, Bikes On Hand, Brick Patio, Lawn Games, Den That’s Stocked w/Board Games.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered

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Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Charming, Renovated Island Cottage – Shelter Island License #: 012-2017. Beach Chairs, Umbrella, Rafts, Towels, 15 X 26 Cedar Deck.

Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets

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Menantic Creek, NY

Shelter Island, Long Island Vacation Rentals

Beautiful, Waterfront Home w/Dock & Heated Gunite Saltwater Pool! Kayaks, A Paddle Boat, BBQ, Fire Pit, There Is Also A Deep Water Mooring!

Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Considered

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Stylish Shelter Getaway! Private Dock. Heated Saline Pool. Clean & Uncluttered, Grey Travertine Patio, Covered Front Porch.

Sleeps: 10
Bedrooms: 5
Bathrooms: 3.5
Pets Considered

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Hay Beach, NY

Shelter Island, Long Island Vacation Rentals

Beach Front, Renovated Summer Home In Picturesque Island, 2 Spacious Private Decks, There Are Bikes, Grill, Wifi, Games, TV & Internet, Xbox.

Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Considered

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Relaxing Getaway In The Heart Of Shelter Island – Great For Families And Couples, Large Backyard, 2 Adult-Sized Bikes Available.

Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets

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Coecles Harbor, NY

Shelter Island, Long Island Vacation Rentals

Secluded Waterfront Oasis, Water Views From Both Sides Of The House, Wrap Around Deck, Crib, Office w/Queen Size Pull Out Couch.

Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Stunning Contemporary w/Heated Gunite Pool w/ Chaise Lounges, Near Wades Beach, Rockers On The Front Porch To Enjoy Morning Coffee.

Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Tranquility Base; Architect-Renovated, Mid-Century Modern With Heated Pool, Cedar Pergola & Wrap Around Patio Bench Seating.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
Pets Considered

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Waterview House w/Heated Gunite Pool, Large Private Yard, 1.6 Acres w/180 Degree Waterviews, Waterview Balcony.

Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Private Wooded Summer House 5 Min. Walk To Wades Beach, Spacious Deck, Beach Chairs, Towels And Gear Provided.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

The Heights, NY

Shelter Island, Long Island Vacation Rentals

Away From It All! Bright, Generous And Well Located 5-Bedroom/3.5 Heights House, Corn Hole, Bocce, Croquet, Ping Pong And Board Games.

Sleeps: 10
Bedrooms: 5
Bathrooms: 3.5
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Silver Beach, NY

Shelter Island, Long Island Vacation Rentals

Luxurious ‘Shelter Island Hideaway’ w/Pool! 2 Jacuzzi Tubs, Teak Lounge Chairs, Charcoal & Gas Grills, Bicycles And Pool Floats.

Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Silver Beach, NY

Shelter Island, Long Island Vacation Rentals

Charming Newly Renovated Home w/Pool On Quiet Street. Near Silver Beach, Great Yard And Outdoor Shower. Ideal For Families w/2-4 Kids.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Considered

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Shelter Island, NY

Shelter Island, Long Island Vacation Rentals

Contemporary Home w/Heated Saltwater Pool Within An Enclosed Patio & Waterviews On Shelter Island, Wraparound Porch w/Furniture.

Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Silver Beach, NY

Shelter Island, Long Island Vacation Rentals

Waterfront Home w/Plenty of Private Beach And Lots Of Room To Swim, Play, And Relax, Deck Overlooking The Harbor.

Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

The Heights, NY

Shelter Island, Long Island Vacation Rentals

Great For Families, Victorian 4 Bedroom House + Beach Club, Large Bright Screened In Porch, Fenced Yard.

Sleeps: 6
Bedrooms: 4
Bathrooms: 2
Pets Considered

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

The Heights, NY

Shelter Island, Long Island Vacation Rentals

Lovely 3 Bedroom Home On Ice Pond, Long Wide Deck, Large Fenced In, Perennial Garden, Piano, Few Blocks From Sunset Beach.

Sleeps: 5
Bedrooms: 3
Bathrooms: 2
Pets Considered

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Hay Beach, NY

Shelter Island, Long Island Vacation Rentals

Island Retreat With Luxury Gunite Pool *New Listing*. 4,500 Sq. Ft. Of Decks & Patios On All 4 Sides Of The House.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets

Long Island NY Vacation Rentals, Long Island NY Vacations, Long Island NY Vacation Homes, Long Island New York Vacation Home Rentals

Hay Beach, NY

Shelter Island, Long Island Vacation Rentals

Elegant Treetop Modern w/Heated Gunite Pool Steps From Beach, TV Room/Library w/Two Balconies, Lush Bamboo Gardens.

Sleeps: 6
Bedrooms: 4
Bathrooms: 4
No Pets