Shelter Island Vacation Rentals
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5 mi
101 rentals in Shelter Island.
Peaceful and Private Shelter Island Getaway
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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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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Classic Waterview Victorian Summer Cottage in Park-Like-Setting
Rental Home
5 bedrooms
5 bathrooms
Sleeps 6
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Charming Studio on Shelter Island
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Spring/Summer Special
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
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Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Sea Pine Cottage
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Charming, Renovated Island Cottage - Shelter Island License #: ********
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Cozy family cottage on Shelter Island
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Shelter Island Farmhouse Pet Friendly with POOL
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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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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Shelter Island, Waterfront, Lazy Days With Stunning Views
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Silver Beach, 3 Bedroom cottage w/ pool
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Recently Renovated Mid-Century Modern House in Shelter Island
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Most private house with pool with ocean view
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Water views, paradise for a month on lovely shelter island for July
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Charming, Historic Cottage
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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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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Turn of the Century Shelter Island Waterfront Cottage
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Private wooded summer house 5 minute walk to Wades Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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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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Contemporary Home on Quiet Country Road/Walk to beach and Fresh Pond
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Magical and serene family compound walking distance to water and walking trails
Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
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Beat the Heat * this Shelter Island Gem!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Cozy Shelter Island all season Rental
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Escape to a Hampton's Island this summer.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Shelter Island beauty - nature and light - modern barn with pool, walk to water
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Lovely Shelter Island cottage with panoramic bay views, secluded, screened...
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Relax By The Pool, Or Walk To The Beach And Restaurants
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Hilltop Cottage Privacy Abounds
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Showing results 1-30 of 101
Frequently Asked Questions about Shelter Island
- Yes, here are some popular vacation rentals in Shelter Island that have a pool:
- Peaceful and Private Shelter Island Getaway
- Stunning, modern with heated Gunite pool near Wades Beach
- Waterfront Charmer on idyllic Shelter Island
- Yes, here are some popular vacation rentals in Shelter Island that have internet access:
- Peaceful and Private Shelter Island Getaway
- Stunning, modern with heated Gunite pool near Wades Beach
- Waterfront Charmer on idyllic Shelter Island
- The best pet friendly rentals in Shelter Island are:
- Peaceful and Private Shelter Island Getaway
- Shelter Island Farmhouse Pet Friendly with POOL
- Silver Beach, 3 Bedroom cottage w/ pool
- Some of the most popular kid friendly rentals in Shelter Island are:
- Peaceful and Private Shelter Island Getaway
- Stunning, modern with heated Gunite pool near Wades Beach
- Waterfront Charmer on idyllic Shelter Island
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