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Shelter Island vacation rentals

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Top-rated vacation rentals in Shelter Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Mastic

4.88 out of 5 average rating, 99 reviews

Cozy home. Comfy living

The whole group will enjoy easy access to everything from this centrally located home. three comfortable bedroom and two bathrooms with a large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. Grace period of 15 mins after check is given after that fees will incur at the nightly rate.

Superhost

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Guest favorite

Guest suite in Branford

4.9 out of 5 average rating, 100 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Guest favorite

Home in North Fork

4.93 out of 5 average rating, 107 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.

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!

Guest favorite

Home in Remsenburg-Speonk

5 out of 5 average rating, 40 reviews

5-Star Listing: Hamptons Oasis, Easy from NYC

Welcome to our coastal retreat. Minutes away from Westhampton Beach and a super-easy commute from NYC. Perfect for families or a group of close friends to get away from it all. A bright, spacious, recently renovated home with light-filled rooms, new floors, coastal decor. Ultrafast Wifi, Alexas, and a new kitchen with the latest appliances. Beautifully landscaped gardens, heated pool, 6-person salt water hot tub (in winter or summer)!

Superhost

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

Cozy Town Cottage - Minutes from EH Town

This charming, historic home is perfect for a young family! The original mudroom with laundry, farm kitchen (no dishwasher), spacious dining and living rooms, two bedrooms and one bathroom welcome you on the main level. Upstairs is a larger bedroom. Take a half mile, tree-covered walk to town, or stop at the grocery store or restaurants just down the street. Absolutely no animals as owner has severe allergy.

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. Cleaning fees for winter stays are 0$.

Guest favorite

Home in North Fork

4.98 out of 5 average rating, 175 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

Cottage in Shelter Island

4.96 out of 5 average rating, 105 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...

Superhost

Home in North Fork

4.64 out of 5 average rating, 11 reviews

Queen Vic Beach House: 5 min to Vineyards & Farms

Location, Location, Location!Nothing like staying directly on the beach. This beach house has five bedrooms, three full bathrooms, sunroom, kitchen Livingroom combo and two bedrooms with en-suites one of which has the most amazing water views and deck.

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, 160 reviews

Sag Harbor House for rent.

Guest favorite

Home in Southampton

4.96 out of 5 average rating, 119 reviews

4 Bed, 2 Bath, Southampton, L.I.

Guest favorite

Home in Shirley

4.9 out of 5 average rating, 136 reviews

Cope near the beach

Guest favorite

Home in Southampton

5 out of 5 average rating, 14 reviews

Pool&Spa open till December

Guest favorite

Home in Westhampton Beach

4.97 out of 5 average rating, 67 reviews

Brand new house with an all year round hot tub.

Guest favorite

Home in East Hampton

4.95 out of 5 average rating, 228 reviews

Private beach Historical House with large property

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

Cabin in Shirley

4.86 out of 5 average rating, 142 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, 128 reviews

"Red House on the Knoll" at Indian Cove

Guest favorite

Home in West Haven

4.94 out of 5 average rating, 18 reviews

Beach House steps from sand & Amazing Views

Guest favorite

Home in East Patchogue

5 out of 5 average rating, 20 reviews

Ho Hum Holiday In Bellport with Pool

Guest favorite

Home in Hampton Bays

4.9 out of 5 average rating, 92 reviews

Private Home minutes from Beach and Nightlife

Guest favorite

Cabin in Rocky Point

4.89 out of 5 average rating, 463 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

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Quick stats about vacation rentals in Shelter Island

  • Total rentals

    130 properties

  • Nightly prices starting at

    $120 before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Family-friendly rentals

    100 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 100 homes with wifi, over 10 homes with a gym, 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

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Shelter Island