Monthly Rentals in Summerland 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, 5 reviews

Stunning Oceanfront Keys Home

JamesRating, 5 stars1 month ago
This is a great place! Everything we could possibly need was at this house! We caught some snappers out back and we LOVED the green light under that water at night, and a few times everyday and night we would go look at the fish. One night a small nurse shark was hanging out too. The kitchen was stocked with all the amenities we could need for our stay (often kitchens we’ve stayed at lacked things we needed for cooking, this place had everything we needed. The area was fun to walk around, and the bike paths off route 1 were also great for exploring. Sunrises were beautiful at the house too. Communication was also great when we had questions about anything. This is the first Airbnb we’ve stayed at where we couldn’t think of anything for improvements.
Guest favorite
Home in Summerland Key
4.75 out of 5 average rating, 8 reviews

Sailfish Dream on Cudjoe Key-28 day minimum

DougRating, 5 stars3 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 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.
Top guest favorite
Home in Big Pine Key
5 out of 5 average rating, 9 reviews

The Tarpon Retreat

JonathanRating, 5 stars8 months ago
First time staying in the Keys with Airbnb after 25 yrs of camp/RV nearby and this was perfect. Canal was great for our 24 ft boat. Neighbors were friendly and also doing longer stays for the lobster and fishing season. Close to the Pub and grocery stores as needed. Easy to walk our dogs in the morning and evening. The kayaks and bikes were a great touch. The living space was great and had everything we needed. We never had to go pick anything up or bring anything to supplement the amenities. Would definitely recommend this for your family or fishing group and will try to rent through Aleksandra at Tarpon Retreat again.

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.

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.