Shelter Island Holiday Rentals
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111 rentals in Shelter Island.
Classic Waterview Victorian Summer Cottage in Park-Like-Setting
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Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
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Cozy family cottage on Shelter Island
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Charming, Historic Cottage
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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
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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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Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12
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Chic Shelter Island Home, Pool and Gardens
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Relax By The Pool, Or Walk To The Beach And Restaurants
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Hilltop Cottage Privacy Abounds
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
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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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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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Beautiful Secluded Family Home on Shelter Island.
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MID-ISLAND RETREAT. Newly renovated, 5 bedrooms, sleeps 8.
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Shelter Island Beauty by the bay! Quiet neighborhood with day dock, bay access.
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Views of beautiful Shelter Island Beach Front Tastefully renovated 1929 Cape.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Modern on wooded lot - 5 min from beach!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Estate on Shelter Island - 200 Feet of Waterfront - 100 Foot Dock
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Chic modern mid century home with saltwater pool and expansive views
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Shelter Island Sun Filled Modern Waterfront Home with Dock
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Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Relax and Enjoy!
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NEW RENTAL! Gorgeous Traditional w/ Pool, 2 minutes from Beaches, Golf, Tennis
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Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
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Relaxing, recreated waterfront home in the heart of West Neck Harbor
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Shelter Island Retreat w/ Outdoor Pool!
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This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!
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Stunning Shelter Island Estate
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Beautiful Ranch Style Shelter Island Home with Private Pool, Close to Golf...
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
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Newly renovated! Quiet, private, short walk to the beach.
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Immaculate Shelter Island Farmhouse with Pool and Minutes to Beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Family friendly home near beach with wonderful deck!
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Waterfront Charmer with boat slip on idyllic Shelter Island for summer rental
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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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Silver Beach, 3 Bedroom cottage w/ pool
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Kick back and unwind
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Summer sun and family fun on Shelter Island
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Family Summer Vacation Home Close to beach 18x42 pool
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Relaxing Shelter Island Getaway - great for families and couples!
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Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach
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Private heated pool and spacious yard. 5 minute walk to the beach.
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Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
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Huge Island Getaway Pool Hot Tub Walk To Beach
Holiday Rental House
6 bedrooms
12 bathrooms
Sleeps 12
Match: Sleeps
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Sleek Shelter Island With Pool, Preserve And Water Rights:
Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Bright, open waterfront house with gorgeous sunsets and private beach
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Showing results 1-50 of 111
Frequently Asked Questions about Shelter Island
- Yes, here are some popular holiday rentals in Shelter Island that have a pool:
- Classic Waterview Victorian Summer Cottage in Park-Like-Setting
- Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
- Cozy family cottage on Shelter Island
- Yes, here are some popular holiday rentals in Shelter Island that have internet access:
- Classic Waterview Victorian Summer Cottage in Park-Like-Setting
- Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
- Cozy family cottage on Shelter Island
- Some of the most popular kid friendly rentals in Shelter Island are:
- Classic Waterview Victorian Summer Cottage in Park-Like-Setting
- Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
- Cozy family cottage on Shelter Island
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