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 favorite
Apartment in Key West
5 out of 5 average rating, 6 reviews

Sunset View Waterfront Studio

SarahRating, 5 stars1 month 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.
Vacation 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 favorite
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!
Home in Key West
5 out of 5 average rating, 4 reviews

Peace on Beach Drive ~hot tub, open water, sunsets

BrandyRating, 5 stars5 days ago
We had a wonderful stay at Peace on Beach Drive. The home was beautifully and comfortably decorated. The kitchen was adequately stocked for daily cooking. Knives were sharp! Bed was comfy. Our favorite place was the upper deck porch where we enjoyed coffee and peaceful mornings then stunning sunsets in the evening. And the water is crystal clear! Christine was super responsive and accommodating. Other perks that weren’t listed and were a nice surprise were that the home has a full size laundry room, covered parking and stand up paddle boards for use. The location was perfect for us, away from the tourists in KW but still a close drive if we wanted to go into the belly of the beast. Additional pros of the location were two neighborhood businesses, Baby’s Coffee & food truck and the Sugar Shark Market right in walking distance. You truly don’t have to leave the Baypoint neighborhood, and why would you want to? ♥️☀️

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.

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