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.

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 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.

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

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.

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Guest favorite

Home in North Fork

4.96 out of 5 average rating, 26 reviews

Waterfront Beach Cottage

Renovated New Suffolk Waterfront Beach Cottage steps from water/beach/restaurants & more w/ water views from practically every window in the heart of the most special neighborhood in the north fork. Perfect for families with twn over full bunks, pvt mstr, grill, outdr shower and new kitchen. Bonus room has comfy couches & sunset views. Dine al fresco with water views or stroll to restaurants, apple picking or famous New Suffolk beach. Minutes from everything your vacation could need, year round.

Guest favorite

Home in North Fork

4.9 out of 5 average rating, 20 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Superhost

Home in Southampton

5 out of 5 average rating, 4 reviews

Charming- In village/bike2beach

Cottage escape spans 1/2 acre; blocks from town & bike ride to Coopers. Gourmet kitchen, livingroom/fireplace, queen-size bedroom downstairs, with laundry and bath. Upstairs: master and guest bedrooms. Outdoors, lush gardens, pool, pergola, cabana, which offer an enchanting sanctuary for relaxation & alfresco living. Whether strolling among fragrant blooms, lounging by the pool, or enjoying outdoor bbq. Timeless charm & contemporary luxury! Month rental -Only avail for aug. + Security deposit

Guest favorite

Home in North Fork

4.93 out of 5 average rating, 103 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Guest favorite

Rental unit in Southampton

4.96 out of 5 average rating, 27 reviews

Beautiful Sunny one bedroom apt in SH. NY.

Enjoy a stylish experience at this centrally-located place. This stunningly-beautiful sunny apartment is located in the heart of Southampton New York, where the sea and the earth elements create the most peaceful setting. The apartment has a private entrance and private bathroom, is located at a short walking distance to Main Street, library, grocery stores, restaurants, shopping stores and pharmacies. PLEASE NOTE: PETS ARE NOT ALLOWED. QUITE TIME 10 PM -9AM

Superhost

Home in Westhampton Beach

5 out of 5 average rating, 4 reviews

Summer Main Home plus cottage close to Main Street

Come relax and enjoy! Beautifully updated Main home with separate cottage. Perfect for in-laws and guests. Each home has its own kitchen, living space, washer/dryer, and outdoor seating. Main house: 4 Br, 3 ba Cottage: 2 Br, 1 ba Outdoor shower for an after beach rinse, 2 patios, pergola, hammock, bbq. A two person kayak available for use; beach passes included. Games, internet, tv... Walk to coffee shops, restaurants, worship, and marina. Bike to beach.

Guest favorite

Houseboat in North Fork

5 out of 5 average rating, 10 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Superhost

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

Guest favorite

Home in North Fork

4.98 out of 5 average rating, 171 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Guest favorite

Home in Hampton Bays

5 out of 5 average rating, 25 reviews

Convenient 2 Bedroom Hampton’s Getaway

Your family will be close to everything when you stay at this centrally-located beach house . Close to beaches, restaurants and shopping. Biking and walking distance to Town and Ocean. You can also take advantage of our close proximity to the North Fork and the wineries. Montauk is about 35 miles east.

Guest favorite

Cottage in Shelter Island

4.96 out of 5 average rating, 104 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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

Other great vacation rentals in Shelter Island

Superhost

Home in North Fork

4.81 out of 5 average rating, 86 reviews

Summer Retreat at the beach , enjoy Wine Country

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

Home in Hampton Bays

5 out of 5 average rating, 9 reviews

Serene Woodland Home Near the Beach

Guest favorite

Home in Hampton Bays

4.91 out of 5 average rating, 88 reviews

Private Home minutes from Beach and Nightlife

Home in Shelter Island

5 out of 5 average rating, 13 reviews

Spacious house with pool.

Guest favorite

Guesthouse in Shelter Island

4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

Superhost

Home in North Fork

4.83 out of 5 average rating, 36 reviews

Farm house with vineyard views

Guest favorite

Home in North Fork

4.88 out of 5 average rating, 8 reviews

Cottage by the beach

Show all

Quick stats about vacation rentals in Shelter Island

Total rentals
140 properties
Nightly prices starting at
G$25,035 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.
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 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.
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 60 homes with a bbq area, over 10 homes with a gym, over 100 homes with air conditioning, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Shelter Island vacation rentals

Top-rated vacation rentals in Shelter Island

Home in North Fork

Home in North Fork

Home in Southampton

Home in North Fork

Rental unit in Southampton

Home in Westhampton Beach

Houseboat in North Fork

Home in Shelter Island

Home in North Fork

Home in Hampton Bays

Cottage in Shelter Island

Home in North Fork

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Shelter Island vacation rentals

Stay near Shelter Island's top sights

Other great vacation rentals in Shelter Island

Home in North Fork

Cottage in North Fork

Home in Hampton Bays

Home in Hampton Bays

Home in Shelter Island

Guesthouse in Shelter Island

Home in North Fork

Home in North Fork

Quick stats about vacation rentals in Shelter Island

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Frequently Asked Questions

Destinations to explore