Clearwater Beach
The classic. Sugar-white sand, the nightly sunset celebration at Pier 60, and restaurants you can reach on foot or by trolley. Condos on the north end are quieter; the marina district keeps you near the action.
Winter Monthly Stays
Snowbird Rentals on Florida's Gulf Coast
Trade the shovel for flip-flops. Monthly vacation rentals across Clearwater Beach, Dunedin, and the barrier islands, where January means 70 degrees and a Gulf sunset every evening.
Winter the way it was meant to be spent
Every winter, thousands of snowbirds from the Northeast, the Midwest, and Canada trade grey skies for the Gulf of Mexico, and Pinellas County is one of the most beloved landing spots in Florida. Mild 70-degree days, the country's best beaches, spring training baseball, and small beach towns where the pace slows down the moment you cross the causeway.
Sunny Orange Stays manages real homes and condos across the Gulf beaches, not hotel rooms: full kitchens, washers and dryers, free parking, and a local team a phone call away all season. Most of our monthly homes host stays of 30 nights or longer, and our winter calendar is the most in-demand inventory we have. Here is everything you need to plan the season.
70° Januarys
Average winter highs run 70 to 76 degrees with the year's lowest humidity and barely any rain. Light-jacket evenings, shirt-sleeve days.
30+ night stays
Our monthly rentals are built for long stays, and many buildings on the beach require them in winter, so you are among neighbors, not weekenders.
Monthly value
Month-long winter stays are priced as seasons, not stacked nightly rates, and they cover the best weather of the Florida year.
A real home base
Full kitchen, in-unit laundry, free parking, and space to host the grandkids when they fly down for a week.
Where snowbirds land
Every town on this coast winters a little differently. All of them share the Gulf, the trolley line, and that unhurried February feeling.
Dunedin
A walkable, golf-cart little town with craft breweries, the Pinellas Trail, Honeymoon Island, and the Blue Jays reporting for spring training right in the neighborhood come February.
Indian Rocks Beach & Indian Shores
Low-rise, low-key beach neighborhoods where the tallest thing around is a pelican on a piling. The snowbird's snowbird towns: quiet mornings, beach walks, and early dinners at beachfront grills.
Treasure Island & Madeira Beach
Wide beaches, John's Pass Village for boat trips and grouper sandwiches, and easy access down to St. Petersburg's museums and dining when you want a city day.
The season, month by month
- December eases you in: quiet early weeks, festive beach towns, and boat parades on the Intracoastal.
- January is prime snowbird time. Mild, dry, calm, and the community of winter regulars is in full swing.
- February brings spring training. Phillies pitchers and catchers report to Clearwater and the Blue Jays to Dunedin mid-month.
- March is the crescendo: Grapefruit League games nearly every day, warming Gulf water, and the coast at its liveliest before the spring-break peak.
- April, if you linger, may be the finest month of the Florida year, and the crowds thin the moment spring break ends.
Plan the details with our guides to the best time to visit, spring training, getting around by trolley, and beach parking.
When to book
Honestly: earlier than you think. January through March monthly homes are our most in-demand inventory, and returning snowbirds re-book their favorite homes for next winter before they fly home in spring.
- Spring Returning guests re-book next winter
- Summer The best homes for Jan–Mar go
- Early fall Good availability still, best picks thinning
- Nov–Dec Late deals happen, selection is luck
Frequently asked questions
When should I book a snowbird rental for this winter?
Six to twelve months ahead for the best selection. Returning guests often re-book before leaving in spring, and the best January through March homes are reserved by late summer. If you are reading this in fall, contact us anyway; calendars shift and we can often find a fit.
What is the minimum stay for a monthly rental?
Most of our monthly homes host stays of 30 nights or longer, and many beach buildings require a 30-night minimum in winter by local rule or association policy. Longer multi-month stays are welcome and common.
How warm is it on the Gulf Coast in winter?
Average highs run about 70°F in January, 72 in February, and 76 in March, with cool comfortable evenings and very little rain. It is the driest, most pleasant stretch of the Florida year. The Gulf itself is cool for swimming until spring, which is what heated pools are for.
Are the rentals equipped for a long stay?
Yes. These are real homes and condos with full kitchens, washers and dryers, linens, WiFi, and parking. You bring your clothes and your clubs; the home takes care of the rest.
Can I bring my dog?
Many of our homes welcome pets. Browse our pet-friendly rentals or tell us what you are traveling with and we will point you to the right homes for a long winter stay.
What is there to do all winter?
More than one winter can hold: the beach itself, spring training baseball in Clearwater and Dunedin from mid-February, the Jolley Trolley up and down the coast, John's Pass boat trips, Honeymoon Island, downtown Dunedin's breweries, St. Petersburg's museums, and a sunset celebration at Pier 60 every single evening.
Your winter home is waiting
With 60+ rentals across the Gulf beaches and a local team that answers the phone all season, the hardest part of your winter will be flying home. Tell us your months and we will find your match.
Browse monthly rentals Talk to our team