Monthly Rentals in Shelter Island

Discover long-term rentals that feel like home, for stays of a month or longer.

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Top Guest favourite
Home in Shelter Island
5 out of 5 average rating, 63 reviews

CASA GYPSEA - a chic and peaceful 3 bedroom house

DavidRating, 5 stars7 months ago
This is a great house on Shelter Island. Our family loved the pool and the basement TV room. The host was accommodating and responsive. Highly recommend!
Home in Shelter Island
5 out of 5 average rating, 3 reviews

New vacation house on the island(new pool)

JamesRating, 5 stars8 months ago
Iwona was a terrific host. The home is immaculately maintained, with high ceilings and large windows looking over beautiful green space. It is a calming environment, both indoors and out. The location is convenient to the town center, a nature preserve, beaches, restaurants, and the north and south ferries. Based on our experience, we recommend highly!
Guest favourite
Home in Shelter Island
5 out of 5 average rating, 9 reviews

All season island beach oasis - Hamptons area!

JoanRating, 5 stars3 weeks ago
Michaela is a super host - for sure! Easy to communicate with. She's kind and patient. Very responsive to the needs of her guests. I would not hesitate to stay here again! The street is quiet, there's a pond in the backyard which attracts all kinds of birds, deer and turkeys. I thoroughly enjoyed the amazing living room with piano. The stores and restaurants are near by and food is easily procured. Michaela has a welcome notebook which lists all the go-to spots on the Island. A true treasure. I will definitely stay here again.
Top Guest favourite
Cottage in Shelter Island
4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Lisagitelson@Gmail.ComRating, 5 stars6 months ago
This is the absolute perfect home for a get away. Everything you need and more is provided. The home is gorgeous, well decorated, and extremely clean. It is even better than the pictures. It feels like a real home, with luxury and artistic touches, not a generically decorated place. Location is perfect, close to it all and still very private. Christopher is an excellent host, responsive, helpful, and gives you your privacy. I can't recommend staying here enough.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.

Stay near Shelter Island's top sights

Mashomack Preserve20 locals recommend
Vine Street Café18 locals recommend
Marie Eiffel Market11 locals recommend
SALT Waterfront Bar & Grill17 locals recommend
IGA Shelter Island7 locals recommend
Commander Cody's Seafood9 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.