Vacation Rentals By Owner In Shelter Island, NY

Showing 86 Of 86 Vacation Rentals

$1209.14

Resort Style Home- Family Friendly

Shelter Island, New York, United States

Located in beautiful Hay Beach, this home has four bedrooms and three full bathrooms. The main bedroom has a king bed and a full bathroom with a private entry to the outdoor deck, pool and shower. Bedroom two has two twins, bedroom three has one twin, and they share a full bathroom. Bedroom 4 has a queen bed and a full private bathroom: large chef's kitchen, living area, dining room, and seating area. A laundry room and small kitchen area accompany bedroom 4.brThe large deck includes an outdoor kitchen, seating area, heated pool, and outdoor shower. Outdoor space is beautifully landscaped and perfect for quiet relaxation.

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$686.31

/ Nightly

Private Vacation Home

Mid-Century Gem with Pool, Fireplace and Steps to Private Beach.

Shelter Island, New York, United States

Escape to our stylish mid-century modern retreat on Shelter Island. A 90 second walk to stunning Crab Creek and a private neighborhood association beach, our home boasts 3 bedrooms, 2.5 baths and an outdoor shower, and sits on nearly an acre of secluded land. The backyard is a private oasis with towering trees, a bamboo forest and a large pool surrounded by beautiful landscaping. Enjoy an indoor fireplace in winter, an outdoor fireplace and grill in summer, or a beach bonfire under the stars.

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$696.92

/ Nightly

Private Vacation Home

Serene 3-bedroom house w/ Pool on Shelter Island

Shelter Island, New York, United States

Consider this lovely house your home away from home while you visit Shelter Island. With 3 cozy bedrooms, heating, and AC, this adorable property is perfect for a relaxing getaway. Beautiful, large 1.5 acre property with inground swimming pool is perfect for a family looking to enjoy the great outdoors. Experience what Shelter Island has to offer with a stay at our house!

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Exceptional(2)

$1754.55

/ Nightly

Private Vacation Home

Chic Shelter Island Home, Pool and Gardens

Shelter Island, New York, United States

You are sure to enjoy a delightful vacation in this sophisticated, fully furnished, three bedroom, two bathroom home with separate, detached studio office.brbrThe living room features a generous wood burning fireplace. The kitchen is well equipped with everything you'll need for meal preparation. brbrThe main bedroom has a queen-sized bed, the second bedroom has a double-sized bed and the third bedroom has two twin-sized beds. The home comfortably sleeps up to six people. brbrThe Gunite pool is 25' x 25' and has a uniform depth of five and a half feet.brbrThe outdoor shower is a very popular amenity during the Summer months as are the perennial and herb gardens.brbrOur home is situated near Crescent Beach, shopping and restaurants -- access to the Hamptons or to the attractions of the North Fork is a short ferry ride away.brbrShelter Island Town License No. 19H-0001brbrPlease note that there are outdoor security cameras (with voice and video recording capability) located on the front porch and at the rear of the home which monitor coming and going.

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Exceptional(52)

$472.87

/ Nightly

Private Vacation Home

Peaceful and Private Shelter Island Getaway

Shelter Island, New York, United States

Enjoy a charming 3 bedroom/2 bath with central AC on an expansive shy acre corner plot located directly across from Sylvester Manor Farm. The land across the street is a preserve and the adjacent lot is undeveloped which allows for plenty of relaxation and privacy. An 800 sqft (open plan) great room with two balconies and large windows is perfect for entertaining or lounging with a good book. The rear balcony descends to a gravel patio area with a fire pit, dining area and charcoal BBQ grill. Owners are very reasonable, responsive, and pet friendly! brbrAbout the Area: Shelter Island is unique to Long Island's east end because it's only accessible by ferry. Upon arriving in S.I., you truly feel like you are in a different world with vacation mode fully setting in. You may be happy to hear that the island has been dubbed the un Hamptons by some because of its low key, relaxed and quiet atmosphere. Shelter Island is home to the 2,100 acre Mashomack Preserve which contains about 10 miles of coastline and represents 1/3 of the island. There you find breathtaking views of fields, creeks, and shoreline. If you are in the mood for an adventure, hop on the north ferry towards Greenport or the south ferry towards Sag Harbor and The Hamptons.brbr Additional notable amenities:brbr -Queen sized air mattress brbr -Workstation with WIFI and a new printer/scannerbrbr -New 55 smart TV with Netflix etc. brbr -Charcoal BBQ grillbrbr-Hammockbrbr -12 cup coffee machinebrbr -New washer/dryerbrbr -Working fireplacebrbr -Outdoor patio setbrbr -Walking distance to mini golfbrbr -Located close to marina & beaches.brbr

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Exceptional(28)

$805.85

/ Nightly

Private Vacation Home

Private wooded summer house 5 minute walk to Wades Beach

Shelter Island, New York, United States

Privately located on a wooded hill near Wades Beach (5 minute walk) and Fresh Pond (1 minute walk). Open concept floor plan. Clean lines and modern furniture. Chef's kitchen with Viking appliances.brbrSpacious deck off the living room perfect for lounging and cocktails and a second deck off the kitchen with outdoor grill.brbr55 in. TV in living room and 40 in. TV in master–both with cable. High-speed WiFi + Sonos sound system.brbrBeach chairs, towels and gear provided.brbrA 5 minute boat ride on South Ferry leads you to Sag Harbor and the Hamptons. A 10 minute boat ride on North Ferry takes you to Greenport and dozens of vineyards on the North Fork.

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Most popular vacation rentals in Shelter Island

Exceptional(28)

$924.17

/ Nightly

Private vacation home

Waterfront Estate on Shelter Island - 200 Feet of Waterfront - 100 Foot Dock

Shelter Island, New York, United States

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Exceptional(28)

$759.77

/ Nightly

Private vacation home

Beautiful, quiet, private, short walk to the beach.

Shelter Island, New York, United States

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Exceptional(28)

$805.85

/ Nightly

Private vacation home

Private wooded summer house 5 minute walk to Wades Beach

Shelter Island, New York, United States

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Exceptional(28)

$847.02

/ Nightly

Private vacation home

Shelter Island Retreat, 5 bdrms near everything!

Shelter Island, New York, United States

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Exceptional(28)

$855.50

/ Nightly

Private vacation home

Lovely home by the sea with dock and heated Gunite pool!

Shelter Island, New York, United States

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Exceptional(28)

$877.28

/ Nightly

Private vacation home

Shelter Island Sun Filled Modern Waterfront Home with Dock

Shelter Island, New York, United States

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Exceptional(28)

$1013.36

/ Nightly

Private vacation home

Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly

Shelter Island, New York, United States

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Exceptional(28)

$1056.81

/ Nightly

Private vacation home

Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12

Shelter Island, New York, United States

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Exceptional(28)

$1013.95

/ Nightly

Private vacation home

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island, New York, United States

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Exceptional(28)

$752.47

/ Nightly

Cottage

Charming, Historic Cottage

Shelter Island, New York, United States

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Vacation Rentals By Owner In Shelter Island, NY

$1209.14

$686.31

$696.92

$1754.55

$472.87

$805.85

Rent a place that suits your needs

Most popular vacation rentals in Shelter Island

$924.17

$759.77

$805.85

$847.02

$855.50

$877.28

$1013.36

$1056.81

$1013.95

$752.47

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