Holiday Homes in Shelter Island
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105 rentals in Shelter Island.
Peaceful and Private Shelter Island Getaway
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Stunning, modern home with all new baths and heated Gunite pool near Wades Beach
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Classic Waterview Victorian Summer Cottage in Park-Like-Setting
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Charming Studio on Shelter Island
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spring/Summer Special
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
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Sea Pine Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming, Renovated Island Cottage - Shelter Island License #: ********
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Cozy family cottage on Shelter Island
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Shelter Island Farmhouse Pet Friendly with POOL
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Silver Beach, 3 Bedroom cottage w/ pool
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Shelter Island, Waterfront, Lazy Days With Stunning Views
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Recently Renovated Mid-Century Modern House in Shelter Island
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Most private house with pool with ocean view
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Water views, paradise for a month on lovely shelter island for July
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming, Historic Cottage
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Mid-century on idyllic pasture like setting with pond
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Turn of the Century Shelter Island Waterfront Cottage
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private wooded summer house 5 minute walk to Wades Beach
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Charming updated home with pool on quiet street. Near Silver Beach
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Beautiful newly built vacation home on Shelter Island Very private
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary near Wade's Beach - 10 min drive to Sunset Beach/Shelter Island
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Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12
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Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach
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Chic Shelter Island Home, Pool and Gardens
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Cozy Shelter Island all season Rental
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Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
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Shelter Island beauty - nature and light - modern barn with pool, walk to water
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Lovely Shelter Island cottage with panoramic bay views, secluded, screened...
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Relax By The Pool, Or Walk To The Beach And Restaurants
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Hilltop Cottage Privacy Abounds
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TRANQUIL RESORT STYLE RETREAT WITH LUXURY GUNITE POOL 2 MIN FROM SANDY BEACHES
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Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
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50's Shelter Island Home w new pool, 3 bed 3 bath
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Family Summer Vacation Home Close to beach 18x42 pool
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Waterfront House With Dock And Private Beach
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Water views Beach and pool!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront farmhouse with dock and south and west sunset view.
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Garden Cottage, Wetlands, Landscaped Gardens, Solar Panels
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Newly renovated! Quiet, private, short walk to the beach.
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NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
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Peaceful Shelter Island sanctuary with heated gunite saltwater pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Family friendly home near beach with wonderful deck!
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Harbor-front gem w/ private beach and open property
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Technicolor Paradise, Architectural Masterpiece Amidst Woodlands & Beaches,...
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Silver Beach Hideaway: newly updated quiet cozy cottage - 4 min walk to beaches!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Shelter Island Hidden Waterfront Gem
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern and Efficient Beachfront Paradise
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Shelter Island Retreat With Pool ...A Stone's Throw Away From The Beach!
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unbelievable water views, 50' heated pool and private beach
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 105
Frequently Asked Questions about Shelter Island
- Yes, here are some popular holiday rentals in Shelter Island that have a pool:
- Peaceful and Private Shelter Island Getaway
- Stunning, modern home with all new baths and heated Gunite pool near Wades Beach
- Classic Waterview Victorian Summer Cottage in Park-Like-Setting
- Yes, here are some popular holiday rentals in Shelter Island that have internet access:
- Peaceful and Private Shelter Island Getaway
- Stunning, modern home with all new baths and heated Gunite pool near Wades Beach
- Classic Waterview Victorian Summer Cottage in Park-Like-Setting
- 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 home with all new baths and heated Gunite pool near Wades Beach
- Classic Waterview Victorian Summer Cottage in Park-Like-Setting
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