Monthly Rentals in Shelter Island Heights

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

Nearby monthly rentals

Superhost

Home in North Fork

4.86 out of 5 average rating, 35 reviews

Waterfront Bungalow w/Private Beach on Peconic Bay

Mary CaroleRating, 5 stars6 days ago

Had a wonderful stay at this beautiful home on the North Fork. Stayed off-season-calm, peaceful and relaxing setting with breathtaking views of the bay. The cottage had everything I needed and felt cozy and welcoming immediately. And very clean. Andrew was friendly, efficient and well organized. I highly recommend this cottage to anyone looking for some R and R!

Guest favorite

Home in Shelter Island

4.92 out of 5 average rating, 12 reviews

Moonlit Manor | Shelter Island Escape w/ NEW Sauna

MelissaRating, 5 stars3 months ago

Absolutely gorgeous spot on Shelter Island! Everything you could possibly want - and I do mean EVERYTHING - in a lovely house. Fully stocked kitchen, bathtub, workout room, fire pit - the list goes on! So close to grocery, wine store, restaurants. The nicest and most attentive hosts, as well. Total gem that we will be coming back to. 🥰

Top guest favorite

Home in North Fork

4.98 out of 5 average rating, 214 reviews

Aqua Vista

ErinRating, 5 stars1 day ago

We have stayed at CJ’s for a few years in a row now and he is an amazing host and his place is wonderful! We love staying here! Highly recommend !

Guest favorite

Home in North Fork

4.92 out of 5 average rating, 299 reviews

1830 Historic garden wing - walk to it all

ScottRating, 5 stars3 weeks ago

Very cute clean residence in the heart of Greenport. Within walking distance to several restaurants. Would stay again.

Explore all

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & traveling professionals

Comfortable accommodations for nomadic and remote working professionals with wifi and dedicated work spaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

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.

Popular amenities for monthly rentals

Kitchen

Wifi

Pet friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Stay near Shelter Island Heights's top sights

Noah's103 locals recommend

The Frisky Oyster75 locals recommend

Mashomack Preserve70 locals recommend

Vine Street Café61 locals recommend

Southold Fish Market54 locals recommend

Aldo's Coffee Company53 locals recommend

Destinations to explore

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