Waterfront villas on one of the island of Florida Keys, USA

For Florida snowbirds, retirees who head south to escape cold weather, winter rentals in Florida offer a variety of lifestyle options without the financial responsibility of owning a second home. Regardless of where you might want to set down roots, seasonal Florida rentals allow you to escape the brutality of northern winters.

Snowbird Rentals With a Taste of Island Life

Island life is unique and laid back. When booking an island rental, always check whether the island has a causeway to the mainland. Otherwise, you may find yourself stranded waiting for a ferry to take you on or off the island. Popular island getaways include:

Boca Grande

Located on Gasparilla Island halfway between Sarasota and Ft. Myers, the quaint village of Boca Grande features almost seven miles of pristine white sand beaches. Known as the “Tarpon Fishing Capital of the World,” Boca Grande is also a recreational boating and sailing mecca.

Vacation Rentals from HomeAway is good booking site for snowbird rentals in Boca Grande. The parent agency, HomeAway has an A+ rating from the Better Business Bureau. In addition to desired dates, HomeAway allows users to enter a number of search parameters including

  • Price range
  • Number of bedrooms
  • Pet accommodations
  • Specific amenities

Once you have narrowed your selections down, click on individual properties for photos and additional information, including renter reviews for that unit. Rates vary based on the size of your rental and the month of the season.

Port Boca Grande (Gasparilla Island) Lighthouse

Anna Maria Island

Known for its sugar-white sand beaches, Anna Maria Island has much more than fun in the sun to offer. Art galleries, museums, aquariums, shopping, and nature parks abound. You can even take in a minor league baseball, indoor football, or professional hockey game.

Like HomeAway, Vacation Rentals By Owner (VRBO) has a top A+ rating from the BBB. The Anna Maria Island VRBO website features almost 1,000 rental units, providing snowbirds with a wide variety of accommodations from which to choose. The VRBO sites feature search parameters similar to those of HomeAway. While rates will vary based on the time during the season you want to go, and the size of your rental, you can expect to pay between one and two thousand per month.

Anna Maria Island aerial photo

Amelia Island

Amelia Island’s Victorian mansions, shopping district, golfing, and quaint seaport village, complete with a town trolley, all provide memories galore for visitors to a destination that is still only 30 minutes away from Jacksonville International Airport. HomeAway: Amelia Island presents rentals in HomeAway’s BBB top-rated familiar easy-to-use search setting.

Amelia Island Beach in Florida, USA

St. George

Just off North Florida’s Gulf Coast lies 28-mile-long St. George Island. Consistently rated one of the top beaches in the U.S., St. George also offers some of the best fishing anywhere and some of the most amazing seafood restaurants in the south. Snowbirds have their choice of everything from beach cottages to homes.

Resort Vacation Properties of St. George Island has a top A+ rating from the Better Business Bureau, as well as accreditation from that organization. Although searching is a little more complicated than some other sites, Resort Vacation Properties allows users to input a wide variety of parameters, including prices.

Beach Houses on St. George Island in Florida

Sanibel and Captiva Islands

A unique feature of these islands is their mostly east-west orientation, resulting in less beach erosion. Island activities include golf, shopping, dining in one-of-a-kind seafood restaurants, and incredible opportunities to observe wildlife in their natural habitat.

HomeAway’s Vacation Rentals in Sanibel Island, with an A+ rating by the BBB provides an excellent place to begin your search for a snowbird rental on Sanibel and Captiva Islands. Rental rates reflect the exclusive nature of the area.

Waterfront Beachfront Luxury Holiday Villas on Sanibel Island Florida

Florida Keys

Start your exploration with the Lower Florida Keys and from there check out Key Largo, Key West, the Islands of Marathon, and Islamorada to provide a full picture. From the quiet solitude of the Lower Keys to the beaches of Marathon, to the exciting sport fishing off Islamorada, the keys have something for everyone. For accommodations, go to Snowbird Seeker to check out the properties they have available for seasonal rental in the Lower Florida Keys. You can also try Key West Vacation Rentals for information and rates on the amazing homes and condos specifically in Key West.

Key West

Snowbird Seasonal Rentals on Florida’s East Coast

Florida is a long state and the east coast offers plenty of hot spots for Florida snowbirds. Rentals in these cities are popular.


Whether you plan to stay in Greater Miami or Miami Beach, you should know this part of Florida is not secluded. For snowbirds who want to be near the action, however, the Miami area may be your cup of tea. It has art, culture, professional sports and all the accouterments of big city life, plus warm winter temperatures. In an area as dense as Miami, stick with a trusted, BBB top rated national rental agency like HomeAway.

Greater Miami

Daytona Beach

Whether you are a NASCAR fan or just seeking sunshine in the winter, Daytona Beach has something for you and your fellow snowbirds. Best known for its beaches and for motorsports, the area has plenty of rental offerings. Start your search with BBB top-rated VRBO: Daytona Beach.

Daytona Beach, Florida from the pier

Ft. Lauderdale

Named after actual forts built during the Second Seminole War, Fort Lauderdale is one of the most popular tourist attractions in the sunshine state. The city features an intricate canal system that gives it the name, “Venice of America.” Various options for vacation rentals in Fort Lauderdale are available on the Airbnb website.