Where to Book Florida Snowbird Rentals

Jim Probasco
Quaint village of Boca Grande
Quaint village of Boca Grande

For Florida snowbirds - retirees who flock south to escape the cold and snow of winter - rentals 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, cheap winter rentals in Florida are one option for escaping that brutal winter.

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.

Where to Book

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. For example, rental rates for this two bedroom beachfront condominium on Gasparilla Island run between $2,600 per month during the fall and $6,000 for the same unit in March.

Anna Maria Island

Anna Maria Island aerial view
Anna Maria Island aerial view

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.

Where to Book

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. For example, monthly rental for this just-off-the-beach one-bedroom villa on Anna Maria Island costs about $1,300 in the summer and $2,500 during prime winter high season.

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.

Where to Book

HomeAway: Amelia Island presents rentals in HomeAway's BBB top-rated familiar easy-to-use search setting. One of the cheaper options for an island getaway, a two-bedroom cottage with a beautiful ocean view rents for about $1,600 per month Nov. thru Apr. and $1,900 from May thru Oct.

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.

Where to Book

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. This one-bedroom townhome with Gulf View rents for $1,175 per month Dec., Jan., and Feb. and $1,320 Oct., Nov., and Mar. Monthly rental is not available at other times for this unit.

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 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. For example, this two bedroom, two bath condominium rents for between $2,100 and more than $5,800 per month, depending on time of season.

Florida Keys

Start your exploration with the Lower Florida Keys and from there check out Key Largo, Key West, the Islands of Marathon, and Islamorado to provide a full picture. From the quiet solitude of the Lower Keys to the beaches of Marathon, to the exciting sport fishing off Islamorado, the keys have something for everyone.


For accommodations, go to BBB Top Rated VRBO: Florida Keys with more than 2,800 listings, for information and rates. Each section of the Keys has different rental rates but this one bedroom, 10th floor ocean front condominium rents for $1,500 to $3,000 per month, depending on season.

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 accoutrements 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. Although rental rates vary widely, this studio apartment in South Beach rents for as low as $1,600 per month (summer/fall) and $2,000 during the high season.

Daytona Beach

Daytona Beach
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 motor sports, the area has plenty of rental offerings.


Start your search with BBB top-rated VRBO: Daytona Beach, where this one bedroom condominium is available for a standard rate of $900 per month. Dates that include special events command higher prices.

Ft. Lauderdale

Named after actual forts built during the Second Seminole War, Fort Lauderdale is one of most popular tourist attractions in the sunshine state. The city features an intricate canal system that gives it the name, "Venice of America."


Vacation rentals are available from VRBO: Fort Lauderdale, with this large one bedroom condominium located five blocks from the beach renting for $1,200 to $1,800 per month, depending on season.

West Palm Beach

West Palm Beach, the oldest large city in South Florida, was incorporated two years before Miami. The area has a tropical rainforest climate with winter temperatures typically above 65 °F.

Accommodations in West Palm Beach can be booked through Vacation Rentals West Palm Beach. On that familiar HomeAway-powered site, snowbirds will find this one bedroom unit renting for $1,860 to $1,922 per month.

South Beach

South Beach, sometimes called SoBe, is actually a neighborhood in the Miami Beach area of Florida. As one of the first areas of Miami Beach to be developed, South Beach has a long and storied history. South Beach seems less crowded than Miami Beach.


HomeAway South Beach has this 1-bedroom apartment listed for around $2,800 per month.


Visitors to Jacksonville will not be surprised to find out it is the largest city in Florida. Centered on the banks of the St. Johns River, the city of Jacksonville lies just 25 miles south of the Georgia border.


VRBO: Jacksonville is an excellent, familiar search engine for Jacksonville where snowbirds will find monthly rental rates of between $1,650 and $1,800 for a beautiful one bedroom condominium in a quiet neighborhood.

West Coast

Along with the islands mentioned above, many people enjoy the west coast of Florida, also known as the Gulf side, because it tends to draw less of the spring break crowd. Favorite places for senior snowbirds to look for rentals include:


Tampa, Florida
Tampa, Florida

In addition to popular tourist attractions like Busch Gardens, Tampa has a lot of scenery, including the Gulf of Mexico as a backdrop.


Finding a place to stay in Tampa is not hard. Check out Tampa Vacation Rentals, part of the Vacation Home Rentals network, which has a BBB A+ rating. Search parameters are easy to set and intuitive to use. This 2-bedroom waterfront condominium rents for about $3,000 per month.


South of Tampa Bay lays the city of Sarasota, an area renowned for its culture, as well as beaches and resorts.


Snowbirds gather in Sarasota every year, many renting accommodations from Vacation Home Rentals Sarasota, which is part of the Vacation Home Rentals network. A one bedroom condominium lists for $2,200 to $2,400 per month.


Based on its proximity to the Everglades, Naples is a popular destination for ecotourism. Be advised - Naples is a small but pricey city with a high concentration of millionaires.


Despite that reputation, HomeAway Naples lists this two-bedroom condominium with lake views located only four miles from the beach for $1,100 to $2,200 per month, depending on season.

Ft. Myers

Fort Myers is the gateway to Southwest Florida, which serves as a major tourist destination.


Get information about accommodations at Vacation Home Rentals where rental rates for a one bedroom, "minutes to the beach" condominium range from $1,250 to $1,450 per month.


Known for its large snowbird population, Venice features golf, fishing, shopping, and a host of other activities popular with seniors.


Rental information is available at VRBO: Venice with this two-bedroom condominium available for between $840 and $2,400 per month, depending on season.

Spring Hill

Founded in 1967, Spring Hill is a relatively new community in Hernando County, Florida. Only 35 miles from Tampa, the community is best known for lower property values, quiet streets, and less crime than some larger municipalities.


Snowbird rental information is available at HomeAway's Vacation Rentals where this 3-bedroom Pool Home is available for as little as $1,500 to $1,700 per month.

Snowbird Tips for Saving Money

Rental accommodations exist to suit any budget, but keep in mind that location and demand help consistently drive the cost of snowbird rentals. There are a few ways to save a bit of money on your rental if you are less picky about your location and proximity to the beach.

Stay Further from the Beach

The closer you are to the water, the higher the rates tend to be. Whether a rental unit has a view of the water can make a difference in price, and one that is located directly on the beach will garner higher rent. For the most affordable prices, an interior rental a couple of blocks from the beach still offers respite from cold winter weather, and the beach is often just a short walk or drive away.

Stay Longer

The cost of Florida snowbird rentals is somewhat driven by demand as well as location. Sometimes a discount is offered for a stay of a month or longer, and if a discount isn't offered upfront, it never hurts to ask. However, in some snowbird markets, a month is considered a short stay since other guests book two to four months at a time.

Stay During the 'Off' Season

When you stay in Florida can make a difference in how much you pay. Rates generally tend to be cheaper in the fall months, and then they rise steadily throughout the winter. Peak rates usually coincide with spring break since a lot of families are looking to get away from old man winter as well.

Book Early

Due to Florida's popularity as a snowbird destination, many guests put in a request for their desired dates for the following year before they head home each year. While most rental agencies don't book that far in advance, they do often accept requests. Once they have the following year's rates established, returning guests who have requested specific dates are often given priority over first-time renters. Talk to your rental agent as soon as you know the dates you hope to spend under the sunny Florida skies.

Rental Insurance

Rental agencies often expect winter rentals to be paid in full six weeks or more before your arrival date. Be sure to check refund policies. When money is only refunded if the rental is re-booked, it is a good idea to look into rental insurance to cover any unexpected circumstances. Rental insurance is usually a percentage of the amount you owe for your stay. It but often covers reimbursement if you can't make it due to a medical emergency and may provide additional coverage during your stay.

Enjoying Florida Life

Regardless of where you go in Florida, and for how long, escaping to the beaches and palm trees of the Sunshine State is an excellent way to make a northern winter shorter, and, therefore, more bearable.

Where to Book Florida Snowbird Rentals