Income Properties

For best income generation, you need an income property you can rent weekly (7 day minimum) or nightly.  With a weekly rental, you can rent in the winter months as well as the summer months. You can also rent during the slower times of the year, typically the Spring and Fall.  Only hotels/resorts and areas zoned commercial allow nightly rentals.

All of the Florida Keys are located in Monroe County. Some of the Keys are incorporated, or in other words, they are their own City, thus have their own regulations.

Monroe County rules are you cannot rent a single family home for less than 28 days.

The Middle Keys are where you want to focus your search for a single family home, if income is the top priority.  This would include Marathon and Key Colony Beach, both are incorporated.  Duck Key is not located in the City of Marathon, and is regulated by Monroe County.

Waterfront properties are the most sought after income properties for vacation rentals.

In the Upper Keys, the only incorporated city is Islamorada, but they do not allow all single family homes to be rented weekly.  Only specific zoning areas can rent on a weekly basis, such as large parcels located directly on the ocean and bay.  Single family homes on canals cannot be rented less than 28 days. For condos in Islamorada, it’s a bit complicated, it depends upon the City’s value of the condo, which changes annually.

Key Largo and Tavernier fall under unincorporated Monroe County and are regulated to a 28 day minimum rental policy.

Now, if you’re looking for a condominium as your income property, associations have their own rules about renting.  If a condo is located in Marathon, that doesn’t mean short term rentals are allowed.  Refer to my list of condos below that do allow owners to rent weekly.


Find Your Single Family Home Income Property in Marathon and Key Colony Beach

Marathon Single Family Homes (includes Key Colony)

*Stirrup Key has a homeowner’s association that does not permit short term rentals.

Key Colony Beach Single Family Homes only


Marathon and Key Colony Beach Half Duplex/Duplex Income Properties:  Very popular for vacation rentals especially on Key Colony Beach.

Half Duplex/Full Duplex in Marathon and Key Colony Beach


Marathon and Key Colony Beach Income Properties – Condos and Townhouses:  not all condos and townhomes permit weekly rentals, in fact, the majority of them do not.  Here are those that allow weekly rentals (or less than a week).

Indigo Reef

indigo reef income properties


Royal Plum

Coco Plum Beach Villas

Coral Lagoon (nightly rentals) due to commercial zoning

Bonefish Yacht Club

Key Colony Point

Sea Isle

Continental Inn

Sunset Beach Club

Key Colony Beach Club Apartments

And the resort properties, Hawk’s Cay and Tranquility Bay.

2 week minimum rentals:  Casa Clara and The Cay (both on Key Colony Beach).

Upper Keys Condos:

Bay Harbour, Lower Matecumbe (Islamorada), please confirm weekly rentals with the Village of Islamorada

Futura Yacht Club (townhouses only) Plantation Key.  The condo “flats” do not qualify due to their appraised value (which is how the Village regulates weekly rentals with condos).  If you see a condo listed in this link, please disregard, as I can’t separate them here.

Mariner’s Club  Key Largo($45K Equity membership paid at closing).

Cheeca Lodge & Spa Islamorada(hotel with nightly rentals)

Ocean Pointe (Tavernier) nightly rentals, confirm with Monroe County

Moon Bay (Key Largo), please confirm weekly rentals with Monroe County