Monthly Rentals in Sugarloaf Key

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

Nearby monthly rentals

Top guest favourite
Flat in Key West
5 out of 5 average rating, 6 reviews

Sunset View Waterfront Studio

SarahRating, 5 stars4 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.
Holiday home in Key West
5 out of 5 average rating, 7 reviews

The Emelina, a Key West Monthly Vacation Rental

SusanRating, 5 stars15 months ago
This is our second time staying in one of Jenna’s properties and it was just as amazing as the first. Beautiful decorated and simple, great location, and extremely responsive (we messaged her asking for a small table and she has someone come by with one by the end of the day).
Guest favourite
Home in Key West
4.82 out of 5 average rating, 11 reviews

KW Beach house with heated pool, dock, accessible

MeghanRating, 5 stars4 months ago
How do you describe perfection? Adrian's house is perfectly situated for the perfect view of Key West flats, the best sunsets of your life, and beautiful coconut trees and flora. We never had to tell the kids to go outside, they swam in the pool, paddle boarded, or fished almost the entire time. The grill was perfect and there are great seafood and meat prices at Winn Dixie. We ate dinner outside most nights in the courtyard, at a huge table with comfortable chairs. seating is everywhere outside. Decks, cabana, dock, poolside, courtyard, etc. Swimming in December is surreal and it was hard to remember winter was everywhere else 😂. We watched movies every night on the huge TV with amazing sound system, and loved sleeping on a king sized Purple Mattress. I'm just still sad and shocked the month is over. What a stay!
Guest favourite
Home in Upper Sugarloaf Key
4.93 out of 5 average rating, 86 reviews

Lighthouse - Beach Houses Key West

TracyRating, 5 stars4 weeks ago
The place was even more beautiful in person. It was perfect for the two of us. The view was stunning. I enjoyed going out on the deck to relax and enjoy the view. I liked how private it was. I loved the pool area. Our host was very responsive and gave great recommendations on places to eat and see. When driving to the house for the first time make sure to follow the directions the host gives you. If you go by your apple maps it will send you to a different location. Mile markers helped too.

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.

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Sugarloaf Key
  6. Monthly Rentals