Florida · 3,452 licensed rentals
Florida Keys vacation rentals, straight from the owner
The Keys hang off the bottom of Florida as one long chain of islands tied together by US-1, the Overseas Highway. Addresses run by mile marker, from MM 0 in Key West up past MM 100 in Key Largo, and locals give directions the same way: bayside or oceanside, and which marker. The farther south you drive, the slower and quieter it gets, until you reach the bars and old houses of Key West.
Every property on this page holds an active Florida vacation rental license. We list the facts from the state record and the area around it. Owners who claim their listing add their own photos, rates and a direct booking link, so you deal with the person who owns the place instead of a platform that charges them up to 15.5% per stay.
Choose your part of the Keys
Areas in The Florida Keys
829 licensed rentals Key West & Stock Island Vacation rentals in Key West 
216 licensed rentals The Lower Keys Vacation rentals in the Lower Keys 
1771 licensed rentals Marathon & the Middle Keys Vacation rentals in Marathon 
206 licensed rentals Islamorada & Plantation Key Vacation rentals in Islamorada 
430 licensed rentals Key Largo & Tavernier Vacation rentals in Key Largo | Area | Best for | Homes | Condos | Total |
|---|---|---|---|---|
| Key West & Stock Island vacation rentals | Walkable trips, nightlife, history, Dry Tortugas day trips | 550 | 279 | 829 |
| The Lower Keys vacation rentals | Boating, snorkeling, fishing, quiet canal-front stays | 205 | 11 | 216 |
| Marathon & the Middle Keys vacation rentals | Families, boaters, longer stays, a central base for day trips | 1,401 | 370 | 1,771 |
| Islamorada & Plantation Key vacation rentals | Fishing charters, boating, sandbar days, bayside sunsets | 169 | 37 | 206 |
| Key Largo & Tavernier vacation rentals | Diving and snorkeling, short trips from Miami, kayaking | 182 | 248 | 430 |
Named properties
Places in the Keys you can ask about today
Planning a the Keys trip
the Keys vacation rental questions
Are these rentals licensed?
Yes. Florida requires a vacation rental license from the Department of Business and Professional Regulation for any home or condo rented more than three times a year for stays under 30 days. Every listing here is built from an active license in that state record. The Keys add a second layer: Key West, Islamorada, Marathon, Key Colony Beach and unincorporated Monroe County each set their own transient rental permit and minimum-stay rules, and some neighborhoods only allow monthly stays. Ask the owner what minimum stay applies to their property before you plan around it.
Why book direct instead of through Airbnb or VRBO?
Since September 15, 2026, Airbnb charges most hosts a host-only fee of about 15.5% of the nightly rate and cleaning fee, and that cost is built into the price you see. When you book with the owner, that money stays out of the deal, and you can ask the person who knows the property about dock space, boat lifts, trailer parking or which side of the island catches the sunset.
How do I book a place that has no booking button yet?
Send an availability request from the listing. We pass it to the owner using the contact on their state license, and they reply to you directly. Listings with a "Book direct" button go straight to the owner's own booking page.
Which part of the Keys should I stay in?
Key Largo and Islamorada are the shortest drive from Miami and the best base for reef trips and fishing charters. Marathon sits in the middle, with family beaches and the Seven Mile Bridge on its doorstep. The Lower Keys are the quiet choice, close to Bahia Honda and Looe Key. Key West is the pick if you want to walk to dinner and catch the boat to the Dry Tortugas.