Shelter Island Heights Vacation Rentals
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Bedrooms
Bathrooms
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Distinctive Features
Distance from
5 mi
121 rentals in Shelter Island Heights.
Newly renovated! Quiet, private, short walk to the beach.
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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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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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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Waterfront Estate on Shelter Island - 200 Feet of Waterfront - 100 Foot Dock
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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Extended Stay Discount! Private Hamptons Cottage with excellent WiFi!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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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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NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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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 Home with Dock
Rental Home
3 bedrooms
5 bathrooms
Sleeps 6
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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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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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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 8
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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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Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Relax and Enjoy!
Rental Home
4 bedrooms
4 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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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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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
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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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 7
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Modern and Efficient Beachfront Paradise
Rental Home
3 bedrooms
4 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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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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Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 5
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Shelter Island Farmhouse Pet Friendly with POOL
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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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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Beautiful Secluded Family Home on Shelter Island.
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Charming, Historic Cottage
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
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Shelter Island Hidden Waterfront Gem
Rental Home
3 bedrooms
3 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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This large Estate on Shelter Island w Heated Pool is the Perfect Summer Rental!
Rental Home
7 bedrooms
7 bathrooms
Sleeps 16
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Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
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Showing results 1-50 of 121
Frequently Asked Questions about Shelter Island Heights
- Yes, here are some popular vacation rentals in Shelter Island Heights that have a pool:See all vacation rentals with a pool in Shelter Island Heights on Tripadvisor
- Yes, here are some popular vacation rentals in Shelter Island Heights that have internet access:
- Shelter Island Hidden Waterfront Gem
- Sea Pine Cottage
- 1880's Boathouse on a hill. Short walk to Crescent Beach.
- The best pet friendly rentals in Shelter Island Heights 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 Heights are:
- Shelter Island Hidden Waterfront Gem
- Sea Pine Cottage
- 1880's Boathouse on a hill. Short walk to Crescent Beach.