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Where to Buy a Vacation Home in Florida

Your guide to the best places to invest in the east coast’s southernmost state.

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You probably know somebody, or know somebody who knows somebody, who has bought a vacation home in Florida at one point—after all, the state boasts one of the top real estate markets in the country. Aside from the primary draws, like year-round warm weather and 1,350 miles of beautiful coastline, the average property tax rate in the Sunshine State is a reasonable 1.02 percent—relatively mild in comparison to many other states, according to

More often than not, purchases are made in the southern portion of the state (i.e. the Keys, Palm Beach, Miami, etc.), but there’s plenty of real estate in central Florida as well, like Orlando, especially for those interested in proximity to theme parks. Not only does a real estate investment enable you to build equity, avoid pricey rent fees year after year, and have a hassle-free vacation when you head south, but it also opens up the opportunity for renting out your new home to seasonal travelers.

Jill Penman, an agent with Sotheby's International Realty, shared her tips for the best cities to check out. "Palm Beach for a classic, elegant environment; Miami Beach for high-end beach condos in a vibrant setting; Key Biscayne for a true coastal vibe just a bridge away from the city; and Coconut Grove for a tropical, laidback feel." She continued to explain, "Naples is also a fantastic city with a beautiful beach. And the Florida Keys offers an idyllic setting with high-end communities like Ocean Reef, an ideal option for avid golfers."

Below, our top picks for where to buy a vacation home in Florida.

Miami Beach

With a luxury housing market that is projected to remain stable in the years to come, Miami is an ideal place to invest in vacation real estate. Between the beautiful beaches, buzzing nightlife, elevated restaurant scene, and abundance of water-related activities, there is never a dull moment in Miami. Purchasing here rules out the need to book at the luxury hotels, and allow vacation home-owners flexibility and the option to be spontaneous about booking travel. And based on the number of travelers the city sees each year, you’ll likely have no issue renting out your property if you choose to go that route.

Key Biscayne

If you crave the excitement of Miami but prefer to stay a little off the beaten path (and away from the crowds), Key Biscayne is an excellent place to invest. Just a quick drive over the Rickenbacker Causeway, this little spit of land is all lush parks and sandy beaches, offering some of Florida’s best views of the ocean, and proximity to a barrier reef and the only federally-recognized underwater archeological trail. This is an especially good choice for those who are interested in water sports, ocean exploration, and low-key luxury.

Orlando or Kissimmee

For those with a family who loves vacations a la Disney and Universal, buying a second home in the City Beautiful, or its neighboring city Kissimmee, is a smart investment. Given how pricey theme park experiences tend to be, eliminating the need to book high-end hotels for a trip to Disney World will likely pay off—especially if you end up renting out your vacation home to other travelers when you’re not using it. Theme parks aside, Orlando has plenty to offer for those looking to purchase a vacation home in a central location. The city itself boasts diverse neighborhoods, a luxury dining scene, and great nightlife; plus, both Orlando and Kissimmee are only a one-to-two hour drive from beautiful beaches like those in St. Augustine or the stretches of sand along the Gulf Coast.

Key West

Whether you’re an avid diver coming to Key West for the spectacular reefs, or you’re chasing that unparalleled sunset and the laid-back island vibes, Florida’s southernmost tip is one of the state’s prettiest spots, full stop. The Old Town is home to an impressive collection of Victorian-style homes, but you’ll also find that beachfront villas and modern, stylish condos abound. Key West is a veritable paradise, and the hours you’ll get in front of the ocean and under the sun will be well worth the investment.

Boca Grande

Life is certainly a little slower out on Gasparilla Island, a pretty little barrier island off of Florida’s Gulf Coast. Boca Grande (Gasparilla’s largest town) is all island vibes, laid-back lifestyle, and charming Old Florida culture. Cars are considered quite rare out here—rather, people often just poke around in golf carts (golfing is another draw to the island)—and you won’t even find a traffic light. Between the picturesque Gasparilla Island State Park, pristine beaches, and relaxed atmosphere, this is a good place to invest in a vacation home if you’re on the hunt for a quiet beach getaway.


If you like to golf at world-class courses, shop luxury labels, and do both while getting some stunning waterfront vistas, Naples is worth looking into for your next vacation home. Nestled on the shores of the Gulf of Mexico and close to Sanibel Island, Marco Island, and Fort Myers, Naples is an excellent place to settle down for a beachside vacation with access to high-end shopping, top-tier cuisine, and tons of fun water sports.

St. Augustine

Famed as the oldest city in the United States, St. Augustine has a lot going for it, history aside—between the centuries-old architecture, the stunning ocean views, eclectic shops and galleries, and diverse cuisine, there is plenty to do in this storied town, and the real estate is considered pretty affordable, to boot. With about six million visitors traveling to this little city each year, you won’t regret purchasing a property so that you can avoid the laborious process of booking hotel rooms or vacation rentals every time you want to come. And if you choose to rent, you shouldn’t have any trouble filling your house during the months that you’re away.


This community-driven college town checks a lot of boxes: relaxed vibes, a dynamic nightlife, and gorgeous natural surroundings. Those looking to purchase a Florida vacation home somewhere where the sun is strong, the sea is nearby, and the town is a happenin’ place will find happiness in Gainesville—and there is plenty of opportunity to rent out your vacation home to those in the college community or to warm-weather seekers.


Those who love to fish will delight at the idea of purchasing a vacation home in the beautiful city of Destin, Florida. While the real estate prices can tend to be on the steep side, this Emerald Coast city boasts some of the whitest sand in the state, beautiful emerald waters of the Gulf, and a thriving marine life, making it one of the world’s “luckiest” fishing towns. From harbourfront condos and townhouses to older homes with character to beachfront properties, Destin offers a little something for anyone looking to cozy up along the Gulf coast.


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