Monthly Rentals in Head of the Harbor

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

Nearby monthly rentals

Top guest favourite
Flat in Saint James
5 out of 5 average rating, 31 reviews

Lovely 1-bedroom rental unit with indoor fireplace

Rating, 5 stars3 months ago
Ahmet’s apartment is spacious and bright, the host is incredibly kind, responds promptly, and shows great generosity in hospitality.Definitely coming back!
Guest favourite
Home in Stony Brook
4.93 out of 5 average rating, 522 reviews

Spacious Studio Apartment- near SBU

JaimeRating, 5 stars3 weeks ago
Gaby’s place was clean and comfortable! She is very kind and it was exactly what we needed for the week. Her check in instructions and directions were thorough and the home is in a beautiful area. Already have our next stay booked :)
Top guest favourite
Cottage in Setauket- East Setauket
5 out of 5 average rating, 84 reviews

Charming historic cottage in Setauket, NY

JosieRating, 5 stars2 months ago
I booked this cottage for my family quickly and only a day or two in advance, barely looking at the listing beyond location and sleeping arrangements. When we arrived, we were all pleasantly surprised at how comfortable and lovely this little home was. I have never encountered such a thoughtfully designed rental. I was recovering from a surgery, had two weary young children, and we were in town for an unexpected funeral. From the games to the beds to the toiletries, every aspect of this cottage soothes and welcomes. Our stay made a difficult time a little easier, and I am very appreciative to Lise for creating such a hospitable and lovely cottage and sharing it with others.
Top guest favourite
Guest suite in Smithtown
4.96 out of 5 average rating, 188 reviews

Cozy Studio near LIRR & 5 miles from Stony Brook U

VincentRating, 5 stars4 days ago
Frank responds immediately to any concerns that you have very friendly. The place was a deal.What a great price for a beautiful location. Look forward to coming back.

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 wifi and dedicated working spaces.

Looking for corporate housing?

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

Stay near Head of the Harbor's top sights

Smith Haven Mall36 locals recommend
Stony Brook Village Center11 locals recommend
Harmony Vineyards9 locals recommend
The Long Island Museum9 locals recommend
Crazy Beans8 locals recommend
Whisper Vineyards7 locals recommend
*Some exclusions may apply in certain geographies and for some properties.