
Monthly Rentals in Kent Island Estates
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Superhost

Home in Chester
5 out of 5 average rating, 3 reviewsKent Island Time-Waterfront
MariaRating, 5 stars2 weeks ago
We stayed here for three nights as a family of four and a dog. The place is very spacious, clean and comfortable, with a wonderful view of the bay. It is located conveniently between Annapolis and Saint Michaels, making it easy to take day trips to these destinations and visit a number of quaint towns around the area. We had a wonderful time and would love to come back again.
Top guest favorite

Apartment in Chester
4.97 out of 5 average rating, 262 reviewsCozy Waterfront Apartment Chester, MD
BrettRating, 5 stars4 months ago
We needed a quiet and private space to relax. Jordan’s space was all of this. We stayed here for a month and hardly ever heard Jordan and her family. Jordan was quick to respond if we had any questions. The bed was very comfortable and the views of the water were nice.
Top guest favorite

Home in Stevensville
5 out of 5 average rating, 109 reviewsKent Island Waterfront Home with Amazing Sunsets
JoanRating, 5 stars1 week ago
Kelly's Kent Island Waterfront Home was the perfect location for a girl's get-away. Her home was incredibly cozy, the waterfront view amazing, and the location couldn't have been better in terms of access to great restaurants/things to do. Kelly was extremely quick to respond to communications and offered up helpful suggestions for local activities and restaurants. I would highly recommend Kelly's home for a girl's trip or a family gathering. I hope to make a return trip sometime soon!
Top guest favorite

Guesthouse in Stevensville
4.99 out of 5 average rating, 270 reviewsWaterfront Getaway - View of bay from your bed
PaulaRating, 5 stars1 week ago
Breathtaking bay beauty provided me with well-needed peace and relaxation. Even though we spent our days running up and down both sides of the Chesapeake, we were able to come back to our centralized Stevensville to this wonderful property. I spent early mornings and sunset-filled evenings bathing in the views of both the bays and creek on the side. The studio, though small, is comfortable for 2. The bathroom is great! Andy and Rachel are friendly and made themselves practically invisible, unless we sought them out, during our stay. There are a variety of restaurants within 20 minutes, most with a water view. DiPaolo's bagel shop is a gem, with a variety of fresh bagels I have never tried...you can watch them being made! We bought delicious sandwiches there both days. We would gladly return in a heartbeat! Thank you, Andy and Rachel!
The comforts of home and great monthly rates
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
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*Some exclusions may apply in certain geographies and for some properties.