As soon as winter arrives, many of us start day dreaming about warm weather, seemingly perpetual sunny skies, and even about the humidity we not long ago dreaded. Perhaps you’re not quite ready to pick up and move to Florida like the snowbirds, but certainly you’d enjoy a long weekend somewhere warm during the cold season, right?

These coastal cities in Florida are sure to satisfy your craving for sun and sand, even in the depths of winter, without making you empty your bank account. To help even the penny-pinching travelers enjoy a break from the cold, we’ve compiled a list of the Florida beach spots that are home to the most affordable winter vacation rentals. It’s time to say ‘see you later’ to that down jacket and ‘hello’ to your cutoffs.

Florida's Cheapest Winter Vacation Rentals: Get the Best Value for Your Beach Getaway this Winter!

1. Clearwater, FL

Situated on Florida's beloved Gulf Coast, Clearwater boasts gorgeous beaches as well as great nightlife and shopping. Although Clearwater is a fun destination to explore any time of year, visitors would be wise to take advantage of its fantastic winter vacation rental rates.

Average Winter Rate: $93 / night

*Fantastic Winter Deals Here: Clearwater vacation rental nightly rates in winter are less than half of the yearly average, which is $216 / night .

Clearwater Vacation Rentals: Browse Now!


2. New Smyrna Beach, FL

Notable art galleries, cute boutiques, inviting cafes and world class beaches make New Smyrna Beach one of Florida's most popular destinations. With Daytona Beach next door, visitors have lots to explore both in and out of town.

Average Winter Rate: $116 / night

*Great Winter Deals Here: New Smyrna vacation rental nightly rates in winter are about $15 less than the yearly average.

New Smyrna Beach Vacation Rentals: Browse Now!


3. St Petersburg, FL

A favorite destination among snowbirds and families, people of all budgets and ages enjoy St. Petersburg, FL. In addition to boasting some of Florida’s most affordable winter vacation rentals, St Petersburg also hosts great beaches, a popular pier as well as a Dali Museum and an enormous iMAX theater for those days when you need a break from the sun.

Average Winter Rate: $121 / night

*Great Winter Deals Here: St. Petersburg vacation rental nightly rates are about $20 less than the yearly average.


St. Petersburg Vacation Rentals: Browse Now!


4. Cocoa Beach, FL

Offering a variety of fun outdoor activities and water sports like kayaking and paddle boarding, Cocoa Beach is a particularly great winter getaway destination for active travelers. With Orlando just an hour away, visitors can easily incorporate a visit to Mickey and Minnie.

Average Winter Rate: $122 / night

Cocoa Beach Vacation Rentals: Browse Now!


5. Ormond Beach, FL

Home to Tomoka State Park, inhabited by Florida’s famous alligators, manatees as well as 160 bird species, Ormond Beach is a great destination for animal lovers, bird watchers, and of course, beach goers planning a winter getaway.

Average Winter Rate: $134 / night

Ormond Beach Vacation Rentals: Browse Now!


6. Cape Coral, FL

With affordable vacation rentals in the winter, over 400 miles of canals as well as great golf courses and beaches, it’s not surprising Cape Coral is such a popular Florida destination.

Average Winter Rate: $161 / night

Cape Coral Vacation Rentals: Browse Now!


7. Bonita Springs, FL

Nicknamed the ‘Gateway to the Gulf’, this Florida hot spot’s sunny winters and gleaming shoreline attract beach goers and boaters from around the world.

Average Winter Rate: $164 / night

Bonita Springs Vacation Rentals: Browse Now!


8. Madeira Beach, FL

Legend has it Madeira Beach was settled by Pirates. The city celebrates this supposed history in its sea-themed boardwalk, spotted with great shops and restaurants. Although the average vacation rental rate is about the same in winter as it is the rest of the year, Madeira Beach still comes in as one of Florida's most affordable winter vacation spots.

Average Winter Rate: $176 / night

Madeira Beach Vacation Rentals: Browse Now!


9. Fort Myers Beach, FL

With white sand beaches, warm water, and fun activities for visitors like baseball games, Fort Myers Beach is a fabulous vacation spot. Enjoy their vacation rental deals in winter!

Average Winter Rate: $177 / night

*Fantastic Winter Deals Here: Fort Myers Beach vacation rental nightly rates in winter are less than half of the yearly average, which is $400 / night .

Fort Myers Beach Vacation Rentals: Browse Now!


10. Bradenton, FL

This quaint Florida city is a thriving bastion of the arts. Local theaters host the American Association of Community Theater competitions, while downtown Bradenton features many studios and galleries. Although Bradenton's winter rates are more than the yearly average nightly rate, this popular Gulf Coast destination remains of the states most affordable coastal cities to visit in the winter.

Average Winter Rate: $192 / night

Bradenton Vacation Rentals: Browse Now!


Start Planning your Florida Getaway Now with Tripping.com!


This article was written by Lexi Perman.