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
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Aug 24 – 31
Guest suite in Shelter Island
4.89 out of 5 average rating, 28 reviewsPrivate two-bedroom stay on Shelter Island
May 8 – 15
Guesthouse in Shelter Island
4.95 out of 5 average rating, 22 reviewsLovely Island Cottage
Dec 17 – 24
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Dec 20 – 27
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
Oct 7 – 14
Cottage in Shelter Island
4.96 out of 5 average rating, 90 reviews3 Bedroom Cottage Gem
Jul 10 – 17
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
Nov 7 – 14
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Sep 14 – 21
Other great vacation rentals in Shelter Island
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
Oct 20 – 27
Cottage in Sag Harbor
5.0 out of 5 average rating, 29 reviewsLuxury Gem At The Heart of Sag Harbor Village
Jun 23 – 30
Home in Greenport
5.0 out of 5 average rating, 35 reviewsBeachfront Greenport Villa
Mar 15 – 22
Apartment in Clinton
4.98 out of 5 average rating, 49 reviewsCozy Shoreline Getaway
Jul 13 – 20
Home in Sag Harbor
5.0 out of 5 average rating, 92 reviewsSecluded Modern Beach Style House
Sep 1 – 8
Guest suite in Old Saybrook
5.0 out of 5 average rating, 37 reviewsCozy Loft Getaway
May 29 – Jun 5
Cottage in Shelter Island
4.94 out of 5 average rating, 32 reviewsCozy Shelter Island 2 Bedroom 1 Bath Cottage
Jul 25 – Aug 1
Home in Greenport
5.0 out of 5 average rating, 29 reviewsHistoric Stunner in Heart of Village
Sep 29 – Oct 6
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
ﺩ.ﺇ441 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 cottage rentals in Shelter Island?
Experience the best of Shelter Island with our cottage rentals, starting at about $280 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 cottage rentals in Shelter Island?
Shelter Island has more than 10 family-friendly cottage 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 70 house rentals with a bbq area in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shelter Island have wifi?
Absolutely! We offer over 100 house rentals with wifi in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Shelter Island?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Fitness-friendly rentals Shelter Island
- Rentals with a fireplace Shelter Island
- Rentals with pools Shelter Island
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- Rentals with outdoor seating Shelter Island
- Kid-friendly rentals Shelter Island
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- Rentals with a washer and dryer Shelter Island
- Family-friendly rentals Shelter Island
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- Pet-friendly rentals Shelter Island
- House rentals Shelter Island
- Monthly Rentals Shelter Island
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