Monthly Rentals in Jamaica Island

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

Nearby monthly rentals

Guest favorite
Apartment in Kittery
4.84 out of 5 average rating, 81 reviews

Heart of Kittery Foreside, Waterfront Apartment

SamuelRating, 5 stars1 week ago
I would highly recommend staying here to anyone visiting Kittery or Portsmouth. Perfect location right in the middle of everything that Kittery has to offer with a nice view of the water. Easy, scenic walk over the bridge into Portsmouth for an excursion. Danny and Linn had amazing recommendations for where to eat, I could eat Lil's crullers every morning and it's right across the street! The space was ideal for myself and would also be perfect for a couple. Clean, tidy, and had everything that you could need. Hope to get the chance to come back someday soon.
Top guest favorite
Guest suite in Kittery
4.97 out of 5 average rating, 147 reviews

Seacoast Suite

MattRating, 5 stars1 day ago
This was my and my wife’s second time staying at Lisa’s place. Just like last time it was clean, comfortable, and easy to find. As a bonus Lisa has a very cute and friendly outdoor cat on property. Lisa is friendly, responsive, and would 100% recommend as a host, we’ll be back! Thank you Lisa!
Guest favorite
Apartment in Kittery
4.98 out of 5 average rating, 80 reviews

Charming retreat in Kittery

WillRating, 5 stars2 days ago
Super cute and cozy stay for our weekend getaway. The instructions left were super helpful and included some local recommendations. Would definitely recommend for a cozy getaway.
Top guest favorite
Guesthouse in Kittery
5 out of 5 average rating, 332 reviews

Newly built, private deck with fire pit.

RajRating, 5 stars3 weeks ago
Such a beautiful stay at Simone's place! She's very responsive and helpful. Highly recommend her place to anyone looking for to return from Kittery/Portsmouth area with wonderful memories.

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.
*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. Maine
  4. York County
  5. Kittery
  6. Jamaica Island
  7. Monthly Rentals