Four Winds of Longboat Key

The Resort & Setting

Units have a casual, beach-house style of decor with private balconies, and the property offers an outdoor pool and tennis courts for guests who want to stay close to home base. The resort holds a strong 4.6 out of 5 rating from 234 Google reviews, reflecting consistent satisfaction with the location and condo-style accommodations.

The Area & Things to Do

Longboat Key itself is the main draw: a protected, sandy shoreline good for swimming, shelling and watching the sunset, reachable on foot from the resort. The island is compact and bike-friendly, with a scattering of local shops and casual restaurants rather than big resort strips. For a wider range of attractions, Sarasota is about 9 miles away and offers museums, theatres and dining, including the well-regarded Ringling Museum (around 11 miles). Mote Marine Laboratory, an aquarium and research centre focused on Gulf Coast wildlife, is roughly 7 miles from the resort, and the powder-sand Siesta Key Beach is a similar distance south. Most owners and renters use a car for these day trips, since the island itself is easily walkable or cyclable but public transport options are limited.

Selling or Renting a Week Here

If you're ready to part with your week at Four Winds of Longboat Key, you can list it for sale or rent directly on BidMyTimeshare.com as an owner-to-owner listing. You set your own asking price, pay a one-time listing fee to publish it, and there's no commission taken when it sells or rents — buyers and renters contact you directly through the platform to work out details.

Because Four Winds of Longboat Key is an independent resort, any resale transfer is handled through the resort's own owners' association or on-site management rather than a branded exchange company's resale desk. Before agreeing on a price with a buyer, both sides should confirm directly with the resort's management: the current transfer or administration fee for changing the deed into the buyer's name, whether the association holds any right of first refusal on resales, how long the transfer process typically takes, and the current annual maintenance fee. These details aren't standardised across independent resorts, so getting them in writing from the resort protects both seller and buyer.

A resale buyer at Four Winds of Longboat Key should expect to receive the deeded week or interest itself, along with whatever usage rights are attached to it under the resort's governing documents — but not any loyalty perks, promotional upgrades, or credits that may have been tied to the original purchase. If exchange network participation matters to you, ask the resort directly whether your specific week is currently enrolled, since this can vary by unit and ownership type.

Practical Notes for Buyers and Renters

Renters and buyers researching Four Winds of Longboat Key are generally looking for direct beach access, a quieter island setting compared with busier Gulf Coast towns, and straightforward condo accommodations rather than a large resort complex with extensive on-site amenities. Winter (December through March) is peak season on this stretch of coast, so availability tends to be tighter and demand higher; the shoulder months of April–May and September–November typically offer calmer conditions and more flexibility for booking a rental or arranging a resale viewing.

Getting There

The resort sits at 2605 Gulf of Mexico Dr, Longboat Key, FL 34228, within easy driving distance of Sarasota and its airport. A rental car is the most practical way to explore beyond the island, even though Longboat Key itself is small enough to navigate on foot or by bike.