Monthly Rentals in Summerland Key

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

Nearby monthly rentals

Superhost
Cottage in Cudjoe Key
4.64 out of 5 average rating, 111 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

Elizabeth CarmenRating, 5 stars1 month ago
Jason’s place was a great place to stay in the keys!! Jason is great at responding great location, clean house only the couch could use a cleaning. It would have been nice if there were trash bags, extra hand soap and extra toilet paper. Other then that it was perfect!!
Superhost
Home in Summerland Key
4.75 out of 5 average rating, 4 reviews

Blackbeard's Hideaway | Cozy cottage on Cudjoe Key

ClaytonRating, 5 stars25 months ago
Blackbeard met our expectations. If you are looking for a quiet neighborhood within an easy drive to the hustle and bustle of Key West, this is the place. The rental agent was extremely responsive and even alerted us to a water issue that impacted the entire Keys. We met several of the neighbors. One of them offered to take us boating and I golfed with another at the Key West Country Club. If you aren't familiar with the Keys, you'll need to get used to the one road in and out. Blackbeard is centrally located between Marathon and Key West and we found plenty to do.
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 weeks 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.
Guest favourite
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 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.

Stay near Summerland Key's top sights

Square Grouper Bar and Grill47 locals recommend
My New Joint27 locals recommend
Galley Grill19 locals recommend
Murray's Market16 locals recommend
Tonio's Seafood Shack & Tiki Bar14 locals recommend
Wharf Waterside Bar & Grill8 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.