Shelter Island Vacation Rentals
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106 rentals in Shelter Island.
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Newly renovated! Quiet, private, short walk to the beach.
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Charming A-frame Home On Private Quiet Road
Rental Home
3 bedrooms
1 bathroom
Sleeps 4
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Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Charming, Renovated Island Cottage - Shelter Island License #: ********
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Relax in this Spacious, Light-Filled Vacation Home with Pool in Silver Beach
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Stunning Shelter Island Estate
Rental Home
8 bedrooms
8 bathrooms
Sleeps 14
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Perfect Family Summer Vacation Home Close to beach 18x42 pool
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Lovely home by the sea with dock and heated Gunite pool!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Enjoy an Old Fashion Winter Holiday with your Family in Historic Harborview Home
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Relaxing Shelter Island Getaway - great for families and couples!
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Private Hamptons Cottage with excellent WiFi!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 5
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Waterfront House With Dock And Private Beach
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful, Spacious Home with Pool, Water Access & Fenced Acre on Private Road.
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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PERFECT FALL GET AWAY! NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
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Stunning, modern with heated Gunite pool near Wades Beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Renovated and Spacious Summer Home with Water View on Picturesque Island.
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Shelter Island Sun Filled Modern Waterfront Retreat!
Rental Home
3 bedrooms
5 bathrooms
Sleeps 6
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Stylish, Country 4 BR Retreat August Preferable
Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
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Stunning Waterfront Estate House with 270 degree sea views on 7 private acres
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Family friendly Shelter Island Home w/ Pool, Hot Tub, Walk to Beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES; PROFESSIONALLY...
Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
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Beat the Heat * this Shelter Island Gem!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Technicolor Paradise, Architectural Masterpiece Amidst Woodlands & Beaches,...
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
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Family friendly home near beach with wonderful deck!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
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Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape.
Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
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Charming Shelter Island Oasis
Rental Home
4 bedrooms
4 bathrooms
Sleeps 5
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Shelter Island Waterfront Home!
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Charming updated home with pool on quiet street. Near Silver Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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The Pool is Open for the Season!
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
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Mid-century on idyllic pasture like setting with pond
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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Gorgeous, Tranquil 9000 Sq Ft Home On Dering Harbor
Rental Home
6 bedrooms
10 bathrooms
Sleeps 12
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TRANQUIL RESORT STYLE RETREAT WITH LUXURY GUNITE POOL 2 MIN FROM SANDY BEACHES
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Perfect Shelter Island Retreat! Modern Barn Privacy & Pool Walk TO BAY & Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Lovely Shelter Island cottage with panoramic bay views, secluded, screened...
Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
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Harbor-front gem w/ private beach and open property
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Hilo Shores 3 bed 2 bath spacious and private. Enjoy West Neck Bay!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Garden Cottage, Wetlands, Landscaped Gardens, Solar Panels
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Contemporary Home on Quiet Country Road/Walk to beach and Fresh Pond
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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The Ultimate Beach House
Rental Home
7 bedrooms
5 bathrooms
Sleeps 15
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Shelter Island, Waterfront, Lazy Days With Stunning Views
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Shelter Island Retreat With Pool ...A Stone's Throw Away From The Beach!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
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Modern and Efficient Beachfront Paradise
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
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Silver Beach Summer Rental
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Summer sun and family fun on Shelter Island
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Sleek Shelter Island With Pool, Preserve And Water Rights:
Rental Home
3 bedrooms
5 bathrooms
Sleeps 8
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Waterfront Modern with pool
Rental Home
4 bedrooms
4 bathrooms
Sleeps 7
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Waterfront Charmer on idyllic Shelter Island
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Frequently Asked Questions about Shelter Island
- Yes, here are some popular vacation rentals in Shelter Island that have a pool:
- Tennis Court, Open and Spacious Living and Dining Areas, Close Proximity to...
- Waterfront Charmer on idyllic Shelter Island
- Shelter Island Hidden Waterfront Gem
- Yes, here are some popular vacation rentals in Shelter Island that have internet access:
- Waterfront Charmer on idyllic Shelter Island
- Shelter Island Hidden Waterfront Gem
- Pristine renovated home within minutes of West Neck harbor
- The best pet friendly rentals in Shelter Island are:
- Shelter Island Hidden Waterfront Gem
- Newly renovated! Quiet, private, short walk to the beach.
- Escape to a Hampton's Island this summer.
- Some of the most popular kid friendly rentals in Shelter Island are:
- Waterfront Charmer on idyllic Shelter Island
- Shelter Island Hidden Waterfront Gem
- Pristine renovated home within minutes of West Neck harbor