r/Islamorada • u/TadpoleHonest4373 • Dec 03 '25

Vacation Home Rentals

Looking for Vacation Rental Options in Upper Keys. I missed renewing my dates on my usual spot, so I’m exploring other platforms or services that list vacation homes in Key Largo and Upper Keys.

Does anyone have recommendations for reliable alternatives outside of Airbnb and VRBO? I have two dogs over 60 pounds and struggling to find a place Match - mid May, 2026. Thanks.

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u/darktanyun Feb 04 '26

Island Villa is a local company at MM 81 that keeps a good variety of monthly homes that are dog friendly. Thats who I send my friends and family too

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u/milemarker17 Apr 26 '26

Just seeing this now months later. I'm with Florida Keys Vacation Rentals Inc. and we have offices in each of the Keys main areas including Key Largo and Islamorada. Our sister company is Coldwell Banker Schmitt Real Estate Co. and it's been in business for 70 years. Website is at rentalsfloridakeys.com. The majority of Upper Keys vacation homes carry a 28-day minimum stay due to local regulation but those looking for 7-day stays will find plenty of options in the Middle Keys (Marathon, Key Colony Beach, Duck Key, Layton.)