Your first winter in Clearwater Beach should feel like living here, not like a long vacation that never quite unpacks. This is the guide we wish every first time snowbird had before they crossed the causeway.
A month or more at the beach is a different trip from a week. You need to know where the groceries are, how to get around without the car, where the doctor is, what happens to your mail, and how to fill the days once the novelty of January sunshine settles into a happy routine.
We live here year round and look after homes for winter guests every season, so this is the practical side of it: settling in, getting around, building a winter routine, and the small things that make a long stay easy. If you are still choosing a home, our snowbird rentals page covers neighborhoods, timing and what the homes include. Every date and fare below was checked with the official source on November 3, 2026.
| Topic | The short answer |
|---|---|
| The home | Kitchen, laundry, linens, WiFi and parking are there when you arrive |
| Transit | PSTA fares cap at $85 a month, $42.50 for seniors |
| Market day | Dunedin Downtown Market, Fridays and Saturdays, 9 am to 2 pm |
| Baseball | Phillies home opener Saturday, February 20, 2027 |
| USPS temporary forwarding covers 15 days to 1 year |
What a month at the beach looks like
The first thing most snowbirds notice is how little they need to bring. Our monthly homes are real houses and condos, not hotel rooms, so they come with a full kitchen, a washer and dryer, linens, WiFi and parking. You bring your clothes, your golf clubs and whatever makes a place feel like yours; the house takes care of the rest.
Give yourself the first two or three days to settle. Do one big grocery run, learn the walk to the sand, find the nearest coffee, and figure out which way the sunset faces from your patio.
Many of the quieter beach neighborhoods require stays of 30 nights or more in winter, which is part of their charm. Your neighbors are other long stay guests and year round residents, not a new group every Saturday, so the streets stay calm and people wave on the morning walk.
Groceries and everyday errands
Plan on one proper stock up when you arrive, then smaller top ups through the week. A rental kitchen is fully equipped, so a month of mostly home cooked breakfasts and lunches is easy, and it leaves the budget free for the dinners out you really want. Ask us for the closest supermarket and pharmacy to your home; we are happy to point you to the ones our guests use.
If you are staying without a car, grocery delivery to the home works well for the heavy items, and the trolley handles the rest. More on that below.
Farmers market mornings
Our favorite weekly ritual for winter guests is the Dunedin Downtown Market. From November through June it sets up in Pioneer Park on Main Street every Friday and Saturday morning, with fresh produce, eggs, meats, cheeses, breads, honey and baked goods, plus plants, soaps and live music. It is dog friendly too.
Go early for the best produce, then stay for a coffee and a wander through downtown Dunedin, which is one of the most walkable small towns on this coast. Our guide to Dunedin has more ideas for the rest of the day.
Good to know: Fridays and Saturdays, 9 am to 2 pm, November to June, John R. Lawrence Pioneer Park, 420 Main Street, Dunedin. Check before you go around holidays. Tampa Bay Markets, the organizer.
Getting around without the car
You may find you barely touch the car once you arrive. Beach parking is limited in peak season, and the causeway traffic on a sunny Saturday is nobody’s idea of a holiday. The good news is that the beach towns are well connected.
The Jolley Trolley and PSTA buses
The Jolley Trolley runs around Clearwater Beach and up the coast to downtown Clearwater, Dunedin, Palm Harbor and the Tarpon Springs Sponge Docks, and the Suncoast Beach Trolley runs down the barrier islands toward St. Pete Beach. Both are part of the Pinellas Suncoast Transit Authority (PSTA) network, so one way of paying covers the trolley and the buses.
This is where a long stay pays off. If you pay with the free Flamingo Fares app or tap the same contactless card each time, PSTA caps what you spend: never more than $85 in a calendar month at the regular fare, or $42.50 a month at the reduced fare for riders 65 and over who register their ID or Medicare card at a PSTA Customer Service Center. Children 8 and under always ride free, and US military veterans ride free on fixed routes with a PSTA Veterans Pass.
Our Clearwater Beach trolley guide maps every route and stop next to our homes, and the beach parking guide helps on the days you do drive.
Good to know: Monthly fare caps of $85 regular and $42.50 reduced apply to Flamingo Fares and tap to pay, not cash. PSTA fares.
The Clearwater Ferry
For a prettier ride, the Clearwater Ferry crosses the harbor between downtown Clearwater, Clearwater Beach Marina near Pier 60, and Dunedin Marina, close to the breweries, shops and restaurants. When we checked in early November it was running Thursday through Sunday. Reservations are encouraged, and walk ons are welcome when there is room. A Saturday market morning in Dunedin by boat is hard to beat. Clearwater Ferry schedules.
Building your winter routine
The best snowbird winters have a rhythm: a beach walk before breakfast, something gentle in the late morning, a long lunch, and a reason to be outside when the sun goes down. Here are the anchors our long stay guests come back to.
Sunsets at Pier 60
Every evening, weather permitting, Pier 60 Park turns into a free street festival with local artisans and street performers, running from two hours before sunset to two hours after. It is the easiest social life on the beach: wander over, watch the sun drop into the Gulf, browse the crafts and walk home. Read more in our guide to sunsets at Pier 60, or see the Sunsets at Pier 60 organizers.
Spring training
If your stay runs into late February, you are in for a treat. Clearwater and Dunedin are both spring training towns. The Philadelphia Phillies play at BayCare Ballpark in Clearwater, and the Toronto Blue Jays at TD Ballpark in Dunedin, which makes it easy to catch a game on a weekday afternoon and still be home for sunset.
For 2027, the Phillies open their Grapefruit League home schedule at BayCare Ballpark on Saturday, February 20, hosting the Blue Jays. The team says 2027 spring training tickets go on sale November 19, 2026, so if the opener matters to you, set a reminder. Our spring training guide covers parking and ballpark tips.
Good to know: Phillies home opener Saturday, February 20, 2027, BayCare Ballpark, Clearwater; tickets on sale November 19, 2026. Phillies spring training. Blue Jays: TD Ballpark spring training.
Book the game, then the home. If baseball is the reason for your trip, look at the February and March schedules first. Late winter is also when our monthly homes are most requested, so the earlier you settle your dates, the more choice you have.
The practical side
A few things are worth sorting out before you leave home, so that nothing interrupts a good winter.
Healthcare basics
Bring enough of any prescription to cover your stay, or ask your pharmacy at home how to transfer it to a Florida branch. The main hospital in town is BayCare’s Morton Plant Hospital at 300 Pinellas Street in Clearwater, whose emergency center is open 24 hours a day. In an emergency, always call 911. BayCare also runs urgent care centers for minor illnesses and injuries. Morton Plant Hospital emergency care.
Mail and packages
For a winter away, the US Postal Service offers a temporary change of address for stays of 15 days up to 1 year. Submit it online and verify your identity, then allow at least 7 to 10 business days for it to take effect. If you would rather have your mail gathered and sent on in one go, USPS also offers a paid Premium Forwarding Service that ships residential mail once a week by Priority Mail. Please check with our team before you send packages or forwarded mail to the home, so we can tell you the best address to use. USPS mail forwarding.
What to pack for a Gulf winter
Pack for warm days and cooler evenings: shorts and sandals, but also a light jacket, a sweater for the breezier nights, and long trousers for the occasional cold front. A hat, reef friendly sunscreen and sunglasses are essentials even in January. Leave the beach towels, kitchen basics and linens at home, since the house has them, and bring a reusable bag for market mornings.
If you are bringing a dog, many of our homes are pet friendly; our pet friendly rentals make it easy to find one for a long stay.
When to book next winter
Honestly: earlier than you think. January through March homes are the ones our guests ask for most, and returning snowbirds often book their favorite home for next winter before they fly north in spring. If you are reading this in November, it is still worth getting in touch, since calendars move and we can often find a fit.
Our monthly rentals page lists every home we offer for stays of 30 nights or more, and our guide to Clearwater Beach in winter will help you picture the season. If you are here over the holidays, our Christmas lights guide has the best evenings out.
Four homes made for a long stay
Here are four of our monthly homes that suit a first winter, each with its own kitchen, laundry, WiFi and parking.
Seas The Day is a two bedroom beach house on Mandalay Avenue with a sunroom, a fenced backyard and an easy walk to the sand. Belle Harbor Suite 71 is a townhome about five minutes on foot from the beach, with a heated community pool, hot tub and fitness center; the association asks for a guest application, so get in touch early. Seahorse Cottage sits in the quiet Carlouel neighborhood at the north end of the beach, with bikes and kayaks for guests. Sea Board Pool House, in the Dunedin area, has a private pool and a big backyard, and one guest wrote that they walked the Pinellas Trail with their dogs every day. All four welcome a pet, subject to each home’s pet policy.
Questions we get asked
How long is a typical snowbird stay in Clearwater Beach?
Our monthly homes are built for stays of 30 nights or more, and many of the quieter beach neighborhoods require that in winter. Longer stays of two or three months are welcome and common.
Can I get around Clearwater Beach without a car?
Yes. The Jolley Trolley and PSTA buses connect the beach with downtown Clearwater, Dunedin and the barrier islands, and the Clearwater Ferry links the beach with downtown and Dunedin on its operating days. With Flamingo Fares or tap to pay, PSTA caps fares at $85 a calendar month, or $42.50 at the reduced fare for riders 65 and over.
When does spring training start in 2027?
The Phillies open their Grapefruit League home schedule at BayCare Ballpark in Clearwater on Saturday, February 20, 2027, against the Toronto Blue Jays. Tickets go on sale November 19, 2026, according to the team.
What should I do about my mail while I am away?
The US Postal Service offers a temporary change of address for 15 days up to 1 year, and a paid Premium Forwarding Service that sends residential mail weekly. Check with our team before sending mail or packages to the home.
What is included in a monthly rental?
Our monthly homes come with a full kitchen, washer and dryer, linens, WiFi and parking. Call us at (727) 449-2700 or email [email protected] with your months and we will suggest homes that fit.
Your winter home
Trade the Shovel for Flip Flops This Winter
Tell us your months, who is coming and whether the dog is too, and we will match you with a home for the season. Questions? Email [email protected].
See you on the sand.