Where to Buy a Second Home in Florida

Alexis Smith-Frady


The hot Florida real estate market continues to flourish as people from other states discover the benefits of living in the Sunshine State: lower housing prices, incredible weather, and no state income tax. This trend holds true for vacation homes and primary residences due to Florida’s miles of beaches and dozens of championship golf courses.

The Sarasota area is as good a place as any to search for a vacation home. Located on Florida’s spectacular Gulf Coast, Sarasota is blessed with fantastic weather, miles of white sand beaches, and a unique topography that includes several special places to live. Longboat Key, Siesta Key, and Anna Maria Island are a series of barrier islands just off the mainland. Most people looking for Florida vacation homes want to be on the water or have an ocean view. Sarasota certainly fits that bill.

If the thought of owning Longboat Key real estate excites you, partner with a licensed real estate agent to help purchase a little slice of paradise. A talented agent knows the area inside and out, from properties on the mainland to homes up and down Florida’s keys. It’s always wise to hire an experienced agent in handling transactions involving waterfront homes, which can be more detailed than transactions for landlocked properties.

Your agent will also assist you in sorting through the various types of vacation properties available, including homes for sale in Siesta Key. One of the benefits of owning a vacation home is renting it out when you aren’t using it and using the rental income to defray the monthly mortgage payments and other costs associated with owning a second property. An agent can steer you toward properties that not only will be ideal for your trips to the Gulf Coast they will also be attractive to visitors who prefer renting a comfortable home rather than staying in a hotel.

Another reason to go with a pro is that Sarasota remains a strong seller’s market, meaning there are more buyers than available properties. When sellers hold most of the cards, purchasers need to be represented by an agent who can get the best possible deal. Here are a few of the best neighborhoods in Florida to purchase a second home.

Siesta Key

Siesta Key
People who buy homes in Siesta Key will find themselves right in the middle of the action. Siesta Key is just offshore from downtown Sarasota and has a plethora of housing options, including condos for those who prefer a low-maintenance lifestyle in a vacation home. Siesta Key is best known for its white sand beach, ranked the top beach in the United States by Tripadvisor in 2020. The beach stretches the entire length of the Gulf Coast side of Siesta Key.

One of the perks of spending time in your Siesta Key vacation home is that you never have to leave the island. Simply head to Siesta Key Village, where you’ll find some 100 businesses: restaurants, bars, shops, and boutiques. Siesta Key Village is walkable and is conveniently located just off the beach. Siesta Key Beach has numerous tennis courts and playgrounds if you're looking for more outdoor recreation. Further down the key are Crescent Beach and Point of Rocks, a series of limestone outcroppings with coral reefs and tide pools. Low-key Turtle Beach, the site of a sea turtle nesting habitat during mating season, makes for a beautiful picnic spot. Boat lovers can take advantage of Turtle Beach’s boat launch.

Longboat Key

Siesta Key
Located a bit off the beaten tourist path, Longboat Key is one of the most desirable locations in the area for vacation homes. Longboat Key sits between Sarasota Bay and the Gulf of Mexico and stretches north toward Anna Maria Island. Longboat Key real estate has mansions right on the beach and other single-family homes on a series of canals leading to Sarasota Bay. There are also myriad condo complexes.

People who purchase condos for sale in Longboat Key have access to some 12 miles of splendid white sand beaches and championship golf courses strategically scattered throughout the island. Mote Marine Laboratory & Aquarium houses manatees, rays, sharks, and otters. Longboat Key’s restaurants range from upscale to fun beach places, and many have water views.

Anna Maria Island

Anna Maria Island
Owners of Anna Maria Island beach homes have one of the most idyllic, exclusive locations to enjoy vacations. Anna Maria Island is a barrier island northwest of Sarasota that abuts Tampa Bay. Vacationers come from around the state — and even around the world — to spend time on the white sand beaches and to swim in the turquoise waters of the Gulf of Mexico. Anna Maria Island has three small towns: Anna Maria, Holmes Beach, and Bradenton Beach.

Anna Maria Island features luxurious waterfront homes on canals that connect to Bimini Bay making it a picture-perfect destination for a vacation home. There are plenty of condo complexes on the island, all in low-rises that give the community a low-key vibe.

Other communities

Other ideal communities for second homes in the Sarasota area include Lido Key, Palmer Ranch, and Lakewood Ranch. Many wonderful neighborhoods and developments stretch south to Naples, which is about two hours south of Sarasota.

Among the factors to consider in shopping for a vacation home are how many days a year you will likely use it and how strong the rental market is in the area. Pick a community that will be awesome for you and one that attracts vacationers year-round, which will help ensure you can rent it out when you are not using it.

In addition to helping you find a great vacation home, an experienced real estate agent can provide endless resources for purchasing a second property. When you’re ready to start shopping for homes for sale in Siesta Key or the surrounding neighborhoods, let Alexis Smith-Frady put her unique approach to work for you. Contact Alexis today to get started!


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