September is when snowbirds (people who move to warmer places for the winter) start to plan their annual move. As the weather begins to turn and the days start to shorten, good options for snowbirds in Florida, Arizona, and the Gulf Coast are getting booked for January through March, and anyone who waits until November tends to find a much shorter list of options, at a higher price.
Most snowbird guides you can find online are about where to go, but this one is about the practical parts: when to book, how long to stay, and how to sign a lease on a place you won't see until you arrive.
When to book
The booking window for a winter stay runs roughly from September through November, and earlier is generally better for the exact reason you might think: the closer snowbird season gets, the less places are available. So, your bargaining position is strongest in early fall, before rentals' calendars start to get booked out.
One tip for if you return to the same area each year: ask your host about next winter before you leave this spring. Plenty of snowbird hosts would rather rebook someone they already know than have to list the place again, so it's worth a conversation.
How long to stay and why it affects your cost
Most snowbirds land somewhere between three and six months, where it's long enough to miss winter weather, while staying under the thresholds that matter for residency and taxes (definitely talk to your own accountant about these ranges; this article can't advise you on tax strategy).
While staying in a seasonal rental, also called a midterm rental (opens in new tab), one thing worth knowing is that the stay length can change what you pay in fees. On MatchBook, the service fee for renters is 3% for stays under six months and drops to 1.5% for stays over six months. On other platforms, you might find discounts are applied for longer stays as well, so if you're thinking of staying in Phoenix for 4-6 months, this might be worth considering when deciding how long to snowbird.
It also doesn't hurt to ask your host directly if a longer booking could potentially get you a better monthly rate. Some may say no, but others may say yes. Hosts who can fill a rental from November through April in a single booking avoid potential gap months, which may make them more inclined to provide a discount to avoid turnover.
Choosing where to snowbird
Locations in Florida, Arizona, and the coast of the Gulf of Mexico tend to get the most attention, but the main thing to consider is what you want your days to look like. If you're someone who wants to have desert mountain views with your morning coffee, the coast might not be for you.
And a few things worth checking before you commit: how far you'll actually be from groceries, hospitals, and the excursions you want to take, if the area is walkable and safe, what parking options you'll have, and what the area is like in February rather than summer, because seasonal towns' character can change completely season to season.
Booking a place you haven't seen
Almost every snowbird books their winter stay from across the country, which is normal, but requires a few extra questions and checks.
You can ask for a live video walkthrough (which hosts may not always be able to accommodate), so you can ask the host questions about the space while they're in it. If the listing doesn't have photos of the parking area, yard, laundry, or view from the window, you can ask them to send photos so you can see those spaces too.
Then, confirm you're dealing with the actual owner or manager before any money moves. This is the part that matters most when you can't be there in person to verify the place or the person you're working with. On MatchBook, every host and listing is reviewed and vetted, and lease signing and rent payments occur on the platform rather than via email or payment apps. And no matter where you book your stay, always review the lease thoroughly before you pay anything, and pay in a way that leaves a record.
What to confirm in the lease
Make sure the dates in the lease match the dates you need. Since seasonal rentals often have bookings lined up, make sure your lease agreement matches your trip dates so you're not left scrambling for a hotel in the days before you head back home.
Ask what's included in the monthly rent you see. Utilities and internet are often bundled into the rent for snowbird rentals, but not always, & a surprise electric bill would definitely put a damper on the New Year celebration.
Ask about extension terms if you want to extend your stay and about cancellation policies in case you need to head home earlier than expected. And if you're bringing a pet (opens in new tab), sort out the pet policies before anything else, so you can rest assured your pup can make the trip with you.
Booking the upcoming winter
Snowbird rentals are really just monthly rentals for a specific group of midterm renters (opens in new tab), so don't think that you have to narrow your search to just a specific type of stay. Knowing where to search (opens in new tab) can make the process much easier and allows you to start your search early, book a stay, and then stop thinking about it until the weather turns.
Find your winter rental on MatchBook
If you're looking for somewhere warm for a few months, browse furnished and unfurnished homes (opens in new tab) on MatchBook for a stay that matches your dates, budget, and needs. Every host and listing is reviewed by our team before it goes live, you can filter by what matters to you, and lease signing and rent payments happen on the platform.
& if you can't find something you like, you can submit a MatchMaker request in your search, and our MatchMaking team will find some options for you!