Monthly Rentals in Shelter Island

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

Nearby monthly rentals

Top guest favorite
Guesthouse in Shelter Island
5 out of 5 average rating, 64 reviews

Bayfront 1BR/2BR detached guesthouse with pool

CarolRating, 5 stars8 months ago
Such a relaxing atmosphere! Quiet and nestled within nature. The view and hot tub were my favorites. The coffee station was an added bonus:) Monica and Stanley were very responsive. If you’re looking for R&R this is the place.
Guest favorite
Home in Shelter Island
5 out of 5 average rating, 10 reviews

All season island beach oasis - Hamptons area!

ElenaRating, 5 stars1 month ago
Michaela has been the perfect host. The house was more than prepared for our stay, with fresh flowers and of course very clean and with everything we possibly needed. She also made sure to have age appropriate toys for my children and bought weights and other items for work out in the house. She also provided recommendations on where to go including gyms and playgrounds. We will be back! Thanks Michaela!
Top guest favorite
Cottage in Shelter Island
4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Lisagitelson@Gmail.ComRating, 5 stars7 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.
Guest favorite
Apartment in Shelter Island Heights
4.91 out of 5 average rating, 246 reviews

Squire Chase House

ErikaRating, 5 stars7 months ago
Terrific location and apartment was superb. Very comfortable, well designed and terrific space, especially the deck.

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 vacation 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

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

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

Destinations to explore

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