Surfside Vacation Rental - Vacation Rentals in Shelter Island Kayak

Quaint DT Greenport Apt - 2 Mi to Shelter Island! From US $208
         

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10.0 (3 Reviews)
Apartment
  • Parking
  • View
  • Balcony/Terrace
Waterfront House With Dock And Private Beach From US $915
         

American Beech Hotel From US $368
         

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9.0 (200 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace
'The Gate House'on Beach front Estate with Dockage. Walk to Village . From US $543
         

Seven Resort Style Inn near Beach From US $341
         

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9.9 (93 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Cottage on Beach front Estate with Dockage .Walk to Village From US $914
         

9.8 (85 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
1820 Whaling Captain's Home - A walk to a coffee or cocktail! From US $811
         

10.0 (56 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Greenport Gem 1, 1 Mile to Ferry! From US $387
         

10.0 (28 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Blue Bay Dream w/Seasonal Outdoor Jacuzzi, Cabana + Office From US $486
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Relaxation in Greenport From US $822
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy Greenport village cottage From US $1,242
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Huge Island Getaway Pool Hot Tub Walk To Beach From US $1,931
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Shelter Island Retreat w/Outdoor Pool! From US $1,594
         

Northfork Townhouse walk to all From US $963
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Pro Tip: Surfsidevacationrental makes it easy to compare the best listings on Surfsidevacationrental homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Surfsidevacationrental homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Shelter Island Kayak.

Weather in Shelter Island Kayak

View the weather forecast for Shelter Island Kayak before booking your Shelter Island Kayak Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Shelter Island Kayak Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Shelter Island Kayak?
How many vacation rentals are available in Shelter Island Kayak?

Currently, the total number of properties listed in 2026 is over 396 in the Shelter Island Kayak area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Shelter Island Kayak.