Shelter Island Villas
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63 rentals in Shelter Island.
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Newly renovated! Quiet, private, short walk to the beach.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Charming, Renovated Island Cottage - Shelter Island License #: ********
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful, Waterfront Home With Dock And Heated Gunite Pool!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Stunning Shelter Island Estate
Holiday Rental House
8 bedrooms
8 bathrooms
Sleeps 14
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Relaxing Getaway in the Heart of Shelter Island - great for families and couples
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Perfect Family Summer Vacation Home Close to beach 18x42 pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Shelter Island Waterfront House With Dock And Private Beach
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Private Hamptons Cottage
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Save time - get the best Shelter Island rentals sent straight to your email!
Beautiful Secluded Family Home on Shelter Island.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Stylish, Country 4 BR Retreat August Preferable
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
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Stunning Waterfront Estate House with 270 degree sea views on 7 private acres
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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NEW LISTING: LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES;...
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
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New Listing: Technicolor Paradise, Architectural Masterpiece Amidst...
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
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Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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Water Views, Renovated Home with Heated Gunite Pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
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Charming Shelter Island Oasis
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
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Shelter Island Waterfront Home!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Spacious beach house with stunning water views
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
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Mid-century on idyllic pasture like setting with pond
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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New Listing: Beautiful Waterview 4-Bedroom Home, Newly Renovated with Huge...
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Family friendly home near beach with wonderful deck!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
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New Listing: Full waterviews, steps to the beach, kayaks available
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
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Waterfront Home W/Private Beach And Lots Of Room To Swim, Play, And Relax
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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NEW LISTING: Farmhouse renovated w/ Convenience + Comfort, Stylish and...
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Contemporary Home on Quiet Country Road/Walk to beach and Fresh Pond
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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The Ultimate Beach House
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 15
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Shelter Island, Waterfront, Lazy Days With Stunning Views
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Hilo Shores, bay access, air conditioned , rec room, spotless , family ready!!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Gorgeous, tranquil 9000 Sq Ft home on Dering Harbor
Holiday Rental House
6 bedrooms
10 bathrooms
Sleeps 12
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Modern and Efficient Beachfront Paradise
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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Summer Sun and Family Fun in Shelter Island
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Waterfront Charmer on idyllic Shelter Island
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Charming 4 Bed/2.5 Bath Cottage In Historic Shelter Island, Walk To Ferry
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Charming, Historic Cottage
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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NEW LISTING: Spacious living, Perfect Getaway, Bright Open Floor Plan, Amazing L
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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New Listing: Renovated, Victorian-Style Home in Sag Harbor, Al Fresco...
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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SHELTER ISLAND: light-filled renovated farmhouse short walk to town and harbor
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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New Listing: Rustic Chic Designer Home on Dering Harbor, Private Dock &...
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Private wooded summer house 5 minute walk to Wades Beach
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!
Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 16
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Bright and Airy West Neck Bay Shingle Style House
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
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Lovely property near beaches and amenities
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Shelter Island Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Charmer on idyllic Shelter Island for summer rental
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Perfect family getaway on beautiful Shelter Island!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pristine renovated home within minutes of West Neck harbor
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Renovated Beach House with Pool, Waterviews, Central Air, and Private Beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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12
Frequently Asked Questions about Shelter Island
- Yes, here are some popular holiday rentals in Shelter Island that have a pool:\n
- \n
- The Ultimate Beach House \n
- Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach \n
- Beautiful, Waterfront Home With Dock And Heated Gunite Pool! \n
- Yes, here are some popular holiday rentals in Shelter Island that have internet access:\n
- \n
- Waterfront Home W/Private Beach And Lots Of Room To Swim, Play, And Relax \n
- Modern and Efficient Beachfront Paradise \n
- Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape. \n
- The best pet friendly rentals in Shelter Island are:\n
- \n
- Waterfront Home W/Private Beach And Lots Of Room To Swim, Play, And Relax \n
- Modern and Efficient Beachfront Paradise \n
- Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape. \n
- Some of the most popular kid friendly rentals in Shelter Island are:\n
- \n
- Waterfront Home W/Private Beach And Lots Of Room To Swim, Play, And Relax \n
- Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape. \n
- Summer Sun and Family Fun in Shelter Island \n