Monthly Rentals in Upper Sugarloaf Key

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

Nearby monthly rentals

Superhost
Home in Summerland Key
5 out of 5 average rating, 12 reviews

Pelico Palm Villa

WilliamRating, 5 stars1 week ago
We rented this place for my 80th birthday celebration with my children and spouses, granddaughter and two great-grandkids. Nine people in all. The accommodations were everything we hoped for and everyone was thrilled with the property and amenities. There were games to play, including table tennis and foosball, a great pool and lots of wildlife on the property including key deer, peacocks and iguanas. The hosts were great to deal with and responsive to all questions. I would recommend this place to anyone with a large family looking for a good venue…you can’t go wrong.
Top guest favourite
Flat in Key West
5 out of 5 average rating, 7 reviews

Sunset View Waterfront Studio

SallyRating, 5 stars2 months 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 favourite
Home in Cudjoe Key
4.93 out of 5 average rating, 178 reviews

106 Newly Renovated House with Oceanview and Pool

JoanRating, 5 stars1 month ago
As always, Michael’s place was spotless, perfectly stocked and just as pictured. We come back here annually to fish at Sugarloaf Marina and are always satisfied. Michaels house is in the perfect location, with the best sunsets, an amazing dock and pool, and the house is always stocked and we're able to relax for another day of tarpon fishing.
Guest favourite
Home in Summerland Key
4.75 out of 5 average rating, 8 reviews

Sailfish Dream on Cudjoe Key-28 day minimum

DougRating, 5 stars2 months ago
Had a very comfortable and enjoyable stay. Accommodations were excellent. Weather was excellent! Warm balmy breezes most days kept humidity down. Lots to do, explored the keys from Islamorada down to Key West, caught the sunset. Spotted deer on Big Pine Key. A very fine month long vacation. Thank you Jeanene.

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.