The Middle Keys are where you want to focus if you’re looking for a property that will generate the best rental income, especially with a single family home.  Marathon and Key Colony Beach are your best options as the municipalities allow for weekly rentals. The Upper Keys and Lower Keys do not allow rentals of less than 28 days with single family homes. Key Largo and the Lower Keys are regulated by Monroe County and Islamorada by the Village of Islamorada.  Duck Key is also located in the County and no rentals of less than 28 days for single family homes. And most definitely waterfront properties, as non waterfront properties do not do well with vacation rentals.

Middle Keys Single Family Homes:

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


Half Duplex or Full Duplex Properties:  Very popular for vacation rentals especially on Key Colony Beach.

Half Duplex/Full Duplex (all of Middle Keys)


Middle Keys Condos and Townhouses:  not all condos and townhomes permit weekly rentals, in fact, the majority of them do not.  Here’s those that allow weekly rentals (or less than a week).

Indigo Reef


Royal Plum

Coco Plum Beach Villas

Coral Lagoon (nightly rentals)

Bonefish Yacht Club

Key Colony Point

Sea Isle

Continental Inn

Sunset Beach Club

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

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

Cheeca Lodge & Spa

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

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