Shelter Island vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Shelter Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Shelter Island vacation rentals
Other great vacation rentals in Shelter Island
Apartment in Greenport
4.86 out of 5 average rating, 145 reviewsQuiet Neighborhood and only steps to Town
Home in Sag Harbor
4.97 out of 5 average rating, 128 reviewsRelax into Coastal Life at a Sun-Drenched Sag Harbor Home
Guesthouse in Shelter Island
5.0 out of 5 average rating, 51 reviewsBayfront 1BR/2BR detached guesthouse with pool
Cottage in Shelter Island
4.96 out of 5 average rating, 90 reviews3 Bedroom Cottage Gem
Guesthouse in Shelter Island
4.96 out of 5 average rating, 24 reviewsLovely Island Cottage
Guesthouse in Shelter Island
4.96 out of 5 average rating, 27 reviewsSleek and Chic cottage/Pool House
Guest suite in Shelter Island
4.9 out of 5 average rating, 29 reviewsPrivate two-bedroom stay on Shelter Island
Guesthouse in Southold
4.95 out of 5 average rating, 43 reviewsSouthold- Adorable 1 Bedroom Cottage
Other great vacation rentals in Shelter Island
Home in Sag Harbor
5.0 out of 5 average rating, 94 reviewsSecluded Modern Beach Style House
Home in Shelter Island
4.97 out of 5 average rating, 78 reviewsModern, spacious SI home with pool
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
Cottage in Shelter Island
4.88 out of 5 average rating, 17 reviewsWaterfront Getaway on Shelter Island
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
Apartment in Greenport
4.97 out of 5 average rating, 65 reviewsLovely 2-bedroom apartment in a historic home
Home in Sag Harbor
5.0 out of 5 average rating, 27 reviewsSag Harbor Modern Oasis
Bungalow in Hampton Bays
4.91 out of 5 average rating, 43 reviewsCozy Bungalow Near the Ocean
Quick stats about vacation rentals in Shelter Island
Total rentals
140 properties
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$120 before taxes and fees
Frequently Asked Questions
Are there pet-friendly vacation rentals in Shelter Island?
Four-legged friends are welcome in Shelter Island. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Shelter Island?
Yes! Work meets play with ease at over 60 vacation rentals in Shelter Island featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Shelter Island vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Shelter Island, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Shelter Island have a gym?
Absolutely! We offer over 10 house rentals with a gym in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Shelter Island have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Shelter Island?
Experience the best of Shelter Island with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Shelter Island?
Shelter Island has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Shelter Island have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Shelter Island have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Shelter Island?
Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with air conditioning, over 60 homes with a bbq area, over 100 homes with wifi, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Kid-friendly rentals Shelter Island
- Rentals with pools Shelter Island
- Pet-friendly rentals Shelter Island
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- Family-friendly rentals Shelter Island
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- House rentals Shelter Island
- Fitness-friendly rentals Shelter Island
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- Monthly Rentals Shelter Island
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