Florida · 9,192 licensed rentals
Fort Myers, Sanibel & Naples vacation rentals, straight from the owner
Southwest Florida is the Gulf coast at its gentlest: wide, shallow beaches, shell-covered sand, mangrove backwaters and a sunset over open water every clear evening. Lee County holds the barrier islands of Fort Myers Beach, Sanibel and Captiva plus the canal city of Cape Coral, and Collier County to the south brings Naples, Bonita Springs and Marco Island at the edge of the Everglades.
Every property listed here carries an active Florida vacation rental license. We start from the state record and the facts about the area, and owners who claim their listing add their own photos, rates and a direct booking link. Hurricane Ian hit this coast hard in 2022 and rebuilding has been ongoing, so the owner is also the best person to tell you what is open and what has changed near their place.
Choose your part of Southwest Florida
Areas in Fort Myers, Sanibel & Naples
1302 licensed rentals Fort Myers Beach (Estero Island) Vacation rentals in Fort Myers Beach 
911 licensed rentals Sanibel, Captiva & Boca Grande Vacation rentals in Sanibel & Captiva 
2889 licensed rentals Cape Coral & Pine Island (Matlacha, St. James City, Bokeelia) Vacation rentals in Cape Coral 
478 licensed rentals Fort Myers, Estero & Lehigh Acres Vacation rentals in Fort Myers 
2236 licensed rentals Naples & Bonita Springs Vacation rentals in Naples 
1376 licensed rentals Marco Island Vacation rentals in Marco Island | Area | Best for | Homes | Condos | Total |
|---|---|---|---|---|
| Fort Myers Beach (Estero Island) vacation rentals | Families with young kids, walkable beach days, sunsets, boating on Estero Bay | 806 | 496 | 1,302 |
| Sanibel, Captiva & Boca Grande vacation rentals | Shelling, birding, biking, quiet beach weeks, couples and families | 486 | 425 | 911 |
| Cape Coral & Pine Island (Matlacha, St. James City, Bokeelia) vacation rentals | Boaters, anglers, pool homes, longer stays, more space for the money | 2,816 | 73 | 2,889 |
| Fort Myers, Estero & Lehigh Acres vacation rentals | Spring training, visiting family, longer stays, value near the airport | 344 | 134 | 478 |
| Naples & Bonita Springs vacation rentals | Dining and shopping, golf, polished beaches, couples and multi-generation trips | 1,559 | 677 | 2,236 |
| Marco Island vacation rentals | Quiet beach weeks, boating, fishing, shorebirds, couples | 859 | 517 | 1,376 |
Named properties
Places in Southwest Florida you can ask about today
Planning a Southwest Florida trip
Southwest Florida vacation rental questions
Are these rentals licensed?
Yes. Florida requires a vacation rental license from the Department of Business and Professional Regulation (DBPR) for any home or condo rented more than three times a year for stays shorter than 30 days. Every listing on this page comes from an active license in that public record, and the license number appears on the listing.
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 every booking, and that cost is built into the nightly price you see. Booking with the owner keeps that fee out of the deal, and you get answers from the person who knows whether the canal has Gulf access, which beach path is closest, or how the place came through the last storm season.
Has the area recovered from Hurricane Ian?
Hurricane Ian made landfall in Lee County in 2022, and Fort Myers Beach and Sanibel took the worst of it. Rebuilding has been going on since, and homes, restaurants and parks have come back on different timelines. Before you book, ask the owner about the property itself and what is open nearby, since that changes faster than any guidebook.
Which part of Southwest Florida should I stay in?
For shelling and wildlife, Sanibel and Captiva. For a lively, walkable beach town, Fort Myers Beach. For a boat at your back door and more space for the money, Cape Coral. For dining, shopping and a polished beach, Naples. For quiet sand and boat trips into the Ten Thousand Islands, Marco Island. Spring training fans usually want Fort Myers itself.