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 favorite
Home in Islamorada
5 out of 5 average rating, 40 reviews

Waterfront private home, pool, dock, sunsets, tiki

Brad & DionRating, 5 stars2 months ago
It is obvious that our every need during our stay was anticipated and answered.The little things that you going to need, but wish you didn’t have to pack are already there waiting for you: blowdryer,soap,shampoo,conditioner,lotion,laundry pods,trash bags,dish pods and dish liquid- there is even a portable,lighted, magnified make up mirror!The kitchen is well equipped with good quality cookware.The cupboards were full of spices/cooking oils. And the chefs knives had a label with the date they had been last sharpened. Publix grocery is less than a mile away which made planning and cooking our meals easy.We enjoyed dinner every night at the large table overlooking the water.Everyone in our party commented on the soft, hotel quality sheets.There were AMPLE bath and beach towels.During the day, we always had something to do without leaving the property. The paddle boards and kayaks,bikes and outdoor games were all in great condition.The pics dont do it justice:BOOK THIS PROPERTY!
Guest favorite
Condo in Islamorada
5 out of 5 average rating, 7 reviews

Islamorada Ray

MattRating, 5 stars2 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 favorite
Home in Islamorada
5 out of 5 average rating, 5 reviews

Seaside Sanctuary in Islamorada

RobertRating, 5 stars1 week ago
Giovanna is an excellent host and the property is exquisite! The beach and pier are full of life and are an excellent way for kids to experience the water and activities, we had a wonderful time and already planning our visit for next year!
Top guest favorite
Cottage in Islamorada
4.95 out of 5 average rating, 39 reviews

Waterfront Cottage Walk to World Famous Lorelei

KathyRating, 5 stars3 weeks ago
We had such a wonderful getaway at the cottage. The house is so charming and filled with character, something we thoroughly enjoy on our vacations. The location afforded us close proximity to shops and restaurants while also giving us a good home base to explore all the keys have to offer. We started each morning with coffee on the dock while enjoying the surrounding beauty. A manatee family were frequent visitors and even played with us while we were kayaking, a core memory experience, for sure. Jackie is a proactive and responsive host, and she was a joy to communicate with. We highly recommend her and her beautiful property. 🌴☀️

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.