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Shelter Island vacation rentals

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Shelter Island vacation rentals

Gym
BBQ grill
Laptop-friendly workspace
Wifi
Air conditioning

Stay near Shelter Island's top sights

Mashomack Preserve70 locals recommend
Vine Street Café61 locals recommend
Marie Eiffel Market41 locals recommend
SALT Waterfront Bar & Grill34 locals recommend
IGA Shelter Island28 locals recommend
Commander Cody's Seafood22 locals recommend

Shelter Island house rentals

Guest favorite

Home in Montauk

4.98 out of 5 average rating, 90 reviews

Sea Roost

Guest favorite

Home in Sag Harbor

4.85 out of 5 average rating, 159 reviews

Sag Harbor House for rent.

Guest favorite

Home in Shirley

4.9 out of 5 average rating, 135 reviews

Cope near the beach

Guest favorite

Home in East Hampton

4.95 out of 5 average rating, 226 reviews

Private beach Historical House with large property

Guest favorite

Home in Old Saybrook

4.97 out of 5 average rating, 119 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Guest favorite

Home in Manorville

4.98 out of 5 average rating, 244 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Guest favorite

Home in Montauk

4.99 out of 5 average rating, 100 reviews

6 minute walk to Ditch Plains Beach

Guest favorite

Home in Sag Harbor

5 out of 5 average rating, 13 reviews

Near Beach & Sag Harbor in the Heart of Hamptons!

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Other great vacation rentals in Shelter Island

Superhost

Home in East Hampton

4.92 out of 5 average rating, 13 reviews

Awesome Casa: Getaway!

Superhost

Cabin in Shirley

4.86 out of 5 average rating, 139 reviews

A-Frame cabin with private beach & epic sunsets

Guest favorite

Cottage in North Fork

5 out of 5 average rating, 12 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Guest favorite

Cottage in Guilford

4.99 out of 5 average rating, 124 reviews

"Red House on the Knoll" at Indian Cove

Guest favorite

Home in East Patchogue

5 out of 5 average rating, 19 reviews

Ho Hum Holiday

Guest favorite

Cabin in Rocky Point

4.89 out of 5 average rating, 455 reviews

Great little place just for a couple

Guest favorite

Home in North Fork

4.91 out of 5 average rating, 11 reviews

Private Beach access along the Wine Trail

Superhost

Home in North Fork

4.84 out of 5 average rating, 37 reviews

Farm house with vineyard views

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Quick stats about vacation rentals in Shelter Island

  • Total rentals

    140 properties

  • Nightly prices starting at

    G$25,078 GYD before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Family-friendly rentals

    110 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    50 properties have a pool

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 70 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 100 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 60 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 10 homes with a gym, over 100 homes with wifi, over 60 homes with a bbq area, over 100 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore