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
Shelter Island house rentals
Home in Sag Harbor
4.97 out of 5 average rating, 123 reviewsRelax into Coastal Life at a Sun-Drenched Sag Harbor Home
Sep 14 – 21
Home in Greenport
4.91 out of 5 average rating, 248 reviews1830 Historic garden wing - walk to it all
Jul 28 – Aug 4
Home in Sag Harbor
4.95 out of 5 average rating, 129 reviewsLuxury Private King Suite + 2 Floor Living Space
Apr 9 – 16
Home in East Lyme
4.96 out of 5 average rating, 103 reviewsWalk to the beach at Black Point, Niantic, Ct
Feb 25 – Mar 4
Home in East Hampton
4.96 out of 5 average rating, 187 reviewsRitz-East Hampton Cottage- 5 stars
Sep 13 – 20
Home in East Hampton
4.93 out of 5 average rating, 138 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Jan 9 – 16
Home in Sag Harbor
4.85 out of 5 average rating, 248 reviewsExclusive Sag Harbor Compound
Nov 2 – 9
Home in East Marion
4.98 out of 5 average rating, 107 reviewsStylish Farmhouse in North Fork
Jan 29 – Feb 5
Other great vacation rentals in Shelter Island
Guesthouse in Sag Harbor
4.84 out of 5 average rating, 115 reviewsSag Harbor Cottage in historic district
Oct 25 – Nov 1
Apartment in Sag Harbor
4.99 out of 5 average rating, 128 reviewsUpdated apartment in historic village home
Sep 5 – 12
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
May 12 – 19
Guest suite in Shelter Island
4.89 out of 5 average rating, 28 reviewsPrivate two-bedroom stay on Shelter Island
May 2 – 9
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Sep 11 – 18
Guesthouse in Shelter Island
4.95 out of 5 average rating, 22 reviewsLovely Island Cottage
Nov 24 – Dec 1
Cottage in Shelter Island
4.88 out of 5 average rating, 16 reviewsWaterfront Getaway on Shelter Island
Oct 17 – 24
Cottage in Shelter Island
4.96 out of 5 average rating, 90 reviews3 Bedroom Cottage Gem
Jun 17 – 24
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 | 3K 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.
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 house rentals in Shelter Island have air conditioning?
Absolutely! We offer over 90 house 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 70 house rentals with a bbq area in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
Are there Shelter Island house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 house rentals 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 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 House Rentals in Shelter Island?
Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with air conditioning, over 10 homes with a gym, over 70 homes with a bbq area, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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