Hyatt Vacation Club at Windward Pointe

The resort and its setting

Hyatt Vacation Club at Windward Pointe is a seaside property on S Roosevelt Blvd, on the quieter, southern side of Key West facing the Atlantic. Suites are two-bedroom configurations with full kitchens, so owners can cook meals in rather than eating out every night, and there's an on-site pool and an airport shuttle, both useful given how close Key West International Airport is to the resort. With a 4.6/5 average from well over a thousand Google reviews, it has a solid track record with guests who've stayed on exchange, as renters, or as owners using their own week.

Key West and things to do nearby

Key West needs little introduction: it's the southernmost point in the continental US, known for sunset gatherings at Mallory Square, the laid-back bars and galleries along Duval Street, and a steady stream of boat trips out to the reef and backcountry flats. The island runs on a mix of cruise-ship day-trippers and longer-stay visitors, and an off-Duval resort like Windward Pointe suits owners who want a kitchen to retreat to after a day of sightseeing or fishing. Key West's Historic Seaport, the Butterfly and Nature Conservatory, and the Hemingway Home are all within easy reach by car, bike, or local shuttle.

Selling or renting a week here

BidMyTimeshare.com is an owner-to-owner marketplace: you set your own asking price, list your week directly, and buyers or renters contact you through the platform. There's no commission on a sale — sellers simply pay a one-time listing fee, which keeps more of the proceeds in your pocket than a traditional broker sale would.

Before listing, it helps to know how Hyatt Vacation Club handles resales. Hyatt doesn't publish an official resale transfer fee, but reports from recent transfers put it at roughly $500–600, and one owner cited around $600 for closing and transfer costs as of May 2025. Hyatt also reportedly holds a right of first refusal on resales, for up to 30 days, meaning the brand can step in and match a buyer's offer before the sale completes — build that window into your expected timeline. Brokers typically quote 8–10 weeks for a transfer to go through from signed contract to new owner on title.

One restriction matters a lot to resale buyers: anyone who buys a Hyatt Vacation Club week on the resale market cannot convert that ownership into World of Hyatt points. If a prospective buyer is counting on points flexibility, make that clear upfront — it avoids disputes later and sets realistic expectations about what they're actually getting: use of the week or unit itself, plus access to Interval International for exchanges, rather than a points-convertible Hyatt product.

Renters, meanwhile, are generally after the practical things this resort offers — the kitchen, the pool, the airport shuttle, and the Key West location itself — rather than any brand loyalty benefit, so rental demand isn't affected by the points restriction in the same way resale prices are.

Practical notes for owners and buyers

Anyone selling should have readily available: the unit size and week or points allotment, the current annual maintenance fee, and confirmation of exchange affiliation (this resort's owners can exchange through Interval International). Buyers should ask for the same information before agreeing on a price, plus written confirmation of how Hyatt's right-of-first-refusal process would affect their purchase timeline. Because transfer costs and the first-refusal window add weeks rather than days, factor that into any move-in or first-use expectations when the deal is agreed.