Florida · 7,533 licensed rentals
Sarasota & Anna Maria Island vacation rentals, straight from the owner
This stretch of the Gulf coast runs from the Manatee River down past Venice, with a chain of barrier islands in front of it: Anna Maria Island, Longboat Key, Lido Key, Siesta Key and Casey Key. The beaches are the headline, but the mainland pulls its weight too, with downtown Sarasota's arts scene, the Ringling estate, and the old riverfront towns of Bradenton and Palmetto.
Every property in this section holds an active Florida vacation rental license. You will find island cottages, Gulf-front condos, canal homes with docks and family houses near I-75. Owners who claim their listing add photos, rates and a direct booking link, so you book with the person who owns the place and skip the platform fee built into the price.
Choose your part of Sarasota
Areas in Sarasota & Anna Maria Island
2772 licensed rentals Anna Maria Island Vacation rentals in Anna Maria Island 
291 licensed rentals Longboat Key Vacation rentals in Longboat Key 
829 licensed rentals Siesta Key Vacation rentals in Siesta Key 
1252 licensed rentals Sarasota, Lido Key & St. Armands Vacation rentals in Sarasota 
537 licensed rentals Venice, Nokomis & Englewood Vacation rentals in Venice 
1852 licensed rentals Bradenton & Lakewood Ranch Vacation rentals in Bradenton | Area | Best for | Homes | Condos | Total |
|---|---|---|---|---|
| Anna Maria Island vacation rentals | Families, beach weeks, bikes and trolley instead of driving | 2,096 | 676 | 2,772 |
| Longboat Key vacation rentals | Quiet beach stays, couples, golf, longer winter stays | 72 | 219 | 291 |
| Siesta Key vacation rentals | Beach lovers, families, walkable village nights | 373 | 456 | 829 |
| Sarasota, Lido Key & St. Armands vacation rentals | Arts and dining, couples, beach plus city in one trip | 1,156 | 96 | 1,252 |
| Venice, Nokomis & Englewood vacation rentals | Shark-tooth hunting, quiet beaches, long winter stays | 421 | 116 | 537 |
| Bradenton & Lakewood Ranch vacation rentals | Larger groups, longer stays, value close to the beaches | 1,407 | 445 | 1,852 |
Named properties
Places in Sarasota you can ask about today
Planning a Sarasota trip
Sarasota 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 shorter than 30 days. Every listing here comes from an active license in that state record, and the license number is shown 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% on every booking, and it is built into the nightly price you see. Booking with the owner keeps that fee out of the deal, and you get straight answers from the person who knows the property: how far the walk to the sand really is, whether the pool is heated, and if the dock fits your boat.
Which beach area should I pick?
Anna Maria Island suits families who want low-rise cottages and a free island trolley. Longboat Key is quieter and condo-heavy. Siesta Key has the famous soft white sand and the liveliest village scene. Lido Key puts you a short walk from St. Armands Circle and a few minutes from downtown Sarasota. Venice and Manasota Key are calmer and known for shark-tooth hunting.
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.