Monthly Rentals in Upper Sugarloaf Key

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

Nearby monthly rentals

Guest favorite
Home in Marathon
4.88 out of 5 average rating, 8 reviews

FL Keys Haven: Modern 2BR/2BA Condo with Balcony

EdwardRating, 5 stars1 month ago
It was our first time in Marathon and we loved staying here! A true hidden gem. The house was beautifully decorated and felt like home as soon as we walked in. Every detail was thoughtful and cozy. Most of all clean, new and modern. The neighbors were friendly and the shared outdoor areas were built for relaxation. We will definitely stay here again! Thank you Kayne and Charles for sharing your lovely home with us! Ed & Yi-Ling
Superhost
Home in Summerland Key
4.67 out of 5 average rating, 3 reviews

Wonderful, pet friendly home for rent with direct

LindaRating, 5 stars22 months ago
Kris notified me that we could check in early. Booked from June 1 - 30, 2023. Check-in was easy and the home was cool when we arrived. We came to fish and relax. There are large TVs in every bedroom...As a person who sleeps with a TV all night, that was very important to me. Loved the location!!! Very peaceful, quiet. Access to both Atlantic and Gulf. Close to Key West. Also, if you Instacart - Publix will deliver! Would stay here again. Kris was great host!
Top guest favorite
Apartment in Key West
5 out of 5 average rating, 6 reviews

Sunset View Waterfront Studio

SarahRating, 5 stars3 weeks ago
Natasha’s place was perfect for our month stay. Was so cozy. Great deck and outside kitchen area. Had everything we needed. Neighborhood was perfect for walks, coffee, tennis and pickleball. Mattress was super comfy. Would come back in a minute.
Guest favorite
Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviews

Relax and Unwind. Enjoy paradise in Cudjoe Key!

PatriciaRating, 5 stars8 months ago
Perfect location for us. House was in great condition and as described. Hosts were very responsive. Caught a couple of tarpon and other small fish in the canal. Saw key deer several times. Can walk to the Square Grouper/The Joint (good restaurants)from the house. Bike bath close by.

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.