9 Best Places to Buy a Vacation Home in Florida

Most lists of Florida vacation home markets rank towns by their beaches. That is the wrong test. The right test is three questions: Can you legally rent the house when you are not using it? What will it cost to carry every month? And how easily can your guests, and you, get there?

I have been in Central Florida real estate since 1996, and for 23 years I ran a title and closing company. I have seen what happens when a buyer finds out after closing that the "rental-friendly" house they bought sits in a zone where short-term rentals are not allowed. This guide compares nine Florida markets on the things that decide whether a vacation home works, then goes deep on the one I know best.

Where is the best place to buy a vacation home in Florida?

For most buyers who want to rent their vacation home part of the year, the Orlando area is the strongest choice in Florida. Osceola and Polk counties have resort communities zoned specifically for short-term rentals, Orlando drew a record 76.7 million visitors in 2025 according to Visit Orlando, and it has the lowest median sale price of the nine markets in this guide. Buyers who will not rent should choose on lifestyle instead.

How do Florida's top vacation home markets compare?

The table below compares all nine markets on price, speed of sale, and the short-term rental rules you will actually live with. Prices are Redfin medians for all home types over the three months ending August 2026 unless noted. Rental rules are summarized from each city or county and can be stricter inside a specific HOA.

Why is Orlando the easiest Florida market to own a rentable vacation home?

Orlando is the easiest Florida market for a rentable vacation home because it pairs zoning that allows nightly rentals with year-round demand. The resort communities southwest of Disney along US-192 and I-4, such as ChampionsGate and Windsor at Westside in Osceola County, were planned for short-term rental use from the start.

That matters more than any view. In a beach town, you are often buying into a neighborhood that is trying to limit renters. In an Orlando resort community, renting is the point, and the clubhouse, pools, and management structure are built around it.

Demand is the other half. In May 2026, Visit Orlando reported 76.7 million visitors in 2025, a 1.8% increase over 2024 and the most of any U.S. destination. Theme park travel runs year-round rather than peaking in one season, so owners I work with often rent through the busy weeks and block off the quieter ones for themselves.

Price helps too. According to the Orlando Regional REALTOR Association, the median home price in its market area was $400,676 in August 2026, with 4.9 months of supply. That is a balanced market, not a frenzy, and it gives buyers room to negotiate.

Much of what is available in these communities is new construction, which brings builder incentives, warranties, and newer systems, along with builder contracts that read very differently from a resale contract. My new construction guide walks through how I represent buyers with builders, and New Construction vs. Resale in Orlando covers the tradeoffs.

Where can you legally rent a vacation home in the Orlando area?

In the Orlando area, whole-home rentals under 30 days are legal mainly in designated resort zones, not in ordinary neighborhoods. Osceola County allows them only inside its short-term rental overlay area or in STRPD zoning. Unincorporated Orange County permits them only in R-3 zoning, and the City of Orlando does not allow whole-home rentals of 1 to 29 days.

Polk County, which covers much of the Davenport and Four Corners area, approves short-term rentals by subdivision, so the rules depend on exactly which community you buy in. Windsor Island Resort, for example, is a Polk community set up for short-term rental use.

Florida law adds a layer. Under Florida Statute 509.032, local governments cannot ban vacation rentals or limit how long or how often you rent unless their rule was adopted before June 1, 2011. That is why rules vary so much from one county line to the next. It does not stop an HOA from setting its own limits.

If you rent more than three times a year for stays under 30 days, you also need a state vacation rental license from the Florida Department of Business and Professional Regulation. Plan to collect Florida sales tax plus the county tourist development tax, which is 6% in Osceola County and 5% in Polk County according to the Florida Department of Revenue.

What do the other eight markets offer vacation home buyers?

Each of the other eight markets suits a different kind of owner. Some are strong for personal use and weak for renting, and a few are the reverse. Here is how I would describe each one to a client.

Miami

Miami is a city first and a beach town second: Little Havana, the Design District, world-class restaurants, and direct international flights. It is also one of the harder places to rent. Next door in Miami Beach, short-term rentals are prohibited in single-family homes and allowed only in condo buildings on the city's approved list. Buy here for your own use.

Naples

Naples is the quiet Gulf Coast choice, with white-sand beaches like Vanderbilt Beach, more than 90 golf courses, and shopping on Fifth Avenue South. The City of Naples requires rentals of at least 30 days, apart from limited exceptions, so it works best as a seasonal home or a monthly rental.

Key West

Key West offers the southernmost point in the continental U.S., conch-style houses, reef diving, and sunset at Mallory Square. Nightly rentals require a transient license, and those licenses are limited and transfer with specific properties. If rental income matters, confirm the license before you write an offer.

Sarasota

Sarasota combines Siesta Key's quartz-sand beach with The Ringling museum and a strong arts scene. The City of Sarasota requires a vacation rental certificate and a minimum stay of seven nights in residential zones, which suits weekly renters better than weekend guests.

Destin

Destin, on the Panhandle, is known for emerald water, deep-sea fishing, and HarborWalk Village. Short-term rentals are allowed in designated zones with city registration. If the home sits outside city limits, Okaloosa County's rules apply instead.

Amelia Island

Amelia Island pairs historic Fernandina Beach with Fort Clinch State Park, salt-marsh kayaking, and bike trails. The City of Fernandina Beach allows short-term rentals only in R-3 zoning or in grandfathered homes and requires a permit and annual inspection.

St. Petersburg

St. Petersburg offers the Salvador Dalí Museum, the St. Pete Pier, a large mural scene, and nearby Gulf beaches. Inside the city, stays under 30 days are limited to three per year unless the property is in a resort overlay or licensed as a hotel.

St. Augustine

St. Augustine, the oldest city in the U.S., is known for the Castillo de San Marcos, St. George Street, and its historic streets. St. Johns County requires short-term rentals to register every year and caps occupancy, so check both county and city rules for the exact address.

What do most vacation home buyers get wrong in Florida?

The most common mistake is trusting a listing that says "short-term rental friendly." Zoning, the HOA's declaration, and the community development district all have a say, and the listing is not a legal document. When I ran closings, the rental restrictions were sitting in recorded documents the buyer had never read.

Three other things catch vacation home buyers off guard:

• The tax bill in year two. A second home does not qualify for Florida's homestead exemption, and the purchase can reset the assessed value. Budget from the new owner's tax estimate, not the seller's current bill.
• CDD assessments. Many newer Orlando-area communities are in a community development district, and that assessment appears on the property tax bill in addition to HOA dues.
• Insurance before the contract, not after. Get a real quote for the specific address during your inspection period. Rental use, roof age, and flood zone all change the number.

To see how taxes, insurance, HOA dues, and CDD fees change the monthly cost, run the numbers in my Orlando mortgage calculator. It includes the fees most payment estimates leave out.

How do you choose between Orlando and the coast?

Choose Orlando if you want to rent the home when you are not there and you value easy access from Orlando International Airport. Choose a coastal market if the water is the reason you are buying and you plan to use the house yourself or rent it by the month.

Some buyers end up with both, starting with an Orlando rental and adding a beach condo later. The decision gets easier once you see the real carrying cost of each option side by side.

If you are still deciding where in Central Florida fits, my neighborhood guides and relocation page are the next step.

Talk through your vacation home plans with Nicole

I'm Nicole Mickle, a Central Florida relocation and new construction specialist. I grew up here, ran a closing company for 23 years, and have worked as a mortgage broker, so I look at a vacation home the way your lender, title company, and HOA will. If you are ready to look at specific communities, schedule a conversation and we will map out where your rental plans are allowed and what the house will really cost.