Monthly Rentals in Upper Matecumbe Key

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

Nearby monthly rentals

Guest favourite
Home in Islamorada
5 out of 5 average rating, 42 reviews

Waterfront private home, pool, dock, sunsets, tiki

ChuckRating, 5 stars1 month ago
Lisa’s ABnB is an awesome place in a beautiful, private setting. For us, it was like home away from home. The set up, both inside and out, is fantastic. Plenty on property to keep us busy and a beautiful setting to just chill. For any questions we had during our stay, our hosts were always responsive. Will met us at check in, gave us a tour and made sure we were comfortable. Great restaurants in the area. All in all a great experience for me and my family.
Guest favourite
Apartment in Islamorada
5 out of 5 average rating, 7 reviews

Islamorada Ray

MattRating, 5 stars3 months ago
We thoroughly enjoyed our stay at this property. It was exactly as described in the listing. The location is in a vibrant, trendy area, surrounded by art galleries and excellent shopping options. The rental itself is high-end, featuring upgraded furnishings and tasteful décor throughout. The outdoor area is both comfortable and well-maintained, providing a perfect space to relax. There are numerous restaurants in the vicinity, and just a short walk across the street offers beautiful sunset views. We were so impressed with our experience that we are already planning to return next year. Thanks, Matt
Guest favourite
Home in Islamorada
4.96 out of 5 average rating, 27 reviews

Heart of Islamorada ~ Private Boat Slip

LindseyRating, 5 stars1 week ago
This place was absolutely perfect for my family! My husband and I brought our two boys and some of their friends. It’s a fisherman’s paradise for sure!! The house was well stocked, exceptionally clean, and very comfortable. I’m currently looking at my calendar to figure out when we can come back.
Top guest favourite
Cottage in Islamorada
4.95 out of 5 average rating, 41 reviews

Waterfront Cottage Walk to World Famous Lorelei

JustinRating, 5 stars3 weeks ago
What an amazing place! My wife and I have stayed in Airbnb properties all over the world, and this was one of our favorites. Exactly as described. Very clean, safe, and comfortable. The location and layout of the property is absolutely perfect and private. This was our first time to Islamorada and this place made it an even better experience. We had a manatee sighting and the deck over the water was my favorite part. Perfect place to have a drink and watch the sunset. If you are planning a trip to the keys, do yourself a favor and stay here.

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