Every year around Labor Day, my phone starts ringing with a version of the same question: We think we want to be in Boca Raton — should we rent for the season first, or just buy?
It is a good question, and the honest answer is that renting first is usually the smarter move for a first-time seasonal resident. It is also a move with a deadline. If you are planning to be here from January through March, the inventory you want is being spoken for right now, in late August and September. Below is what I tell clients about how to use a seasonal lease well — and how to shop for a purchase while you are living in it.
Why a season on the ground beats a season of research
Boca Raton, Delray Beach, and Highland Beach sit within about twelve miles of one another, and buyers routinely assume they are variations on a theme. They are not. A barrier-island condo in Highland Beach, a country club home west of I-95, and a walk-to-Atlantic-Avenue cottage in Delray produce three completely different daily lives — different commutes, different noise, different membership costs, different insurance profiles, different resale dynamics.
A season here answers questions no listing photo can. How far is the drive to your doctor in traffic in February? Does the building’s parking actually work for two cars? Is the golf waitlist twelve months or thirty-six? Do you like the neighborhood in high season, when the population swells and the restaurants book out?
Buyers who rent first tend to buy once. Buyers who skip that step more often buy twice.
The market you’ll be shopping in
Renting first does not mean waiting on the sidelines while the market runs away from you. It means shopping with better information. Here is where Palm Beach County stood in July 2026, per statistics released by MIAMI REALTORS® + RWorld and BeachesMLS:
- Single-family median sale price: $660,090, up 7.64% year over year. Months’ supply: 3.7 months — a seller’s market.
- Condominium median sale price: $312,500, up 3.99% year over year. Months’ supply: 6.7 months — a balanced market, where six to nine months is considered neutral.
- Inventory is tightening across the board. Active listings countywide fell 21.1% year over year, with single-family inventory down 23.32% and condo inventory down 19.26%.
- Sales above $1 million rose 36.5% year over year.
- Cash is dominant. Cash accounted for 47.7% of all closed sales countywide and 57.2% of existing condo sales — roughly double the national share.
Two practical takeaways. First, the single-family and condo segments are not moving in lockstep, so your negotiating position depends heavily on which one you are shopping. Second, in a market where nearly half of closings are cash, financed offers need to be tight and well-documented to compete. Freddie Mac put the 30-year fixed rate at 6.54% in July 2026, so financing costs are a real part of the math for buyers who use it.
The six-month rule that changes your lease math
This is the detail most out-of-state renters do not see coming.
Florida charges its 6% state sales tax, plus any applicable county surtax, on rentals of living accommodations for six months or less, per the Florida Department of Revenue. On top of that, Palm Beach County levies a 6% Tourist Development Tax on short-term stays. Combined, a season-only lease typically carries roughly 12–13% in taxes on the rent.
Rental charges under a bona fide written lease for continuous residence longer than six months are exempt from the state tax. So a seven-month lease can cost meaningfully less per month, all-in, than a four-month lease at the same nominal rent — and it also positions you to be here during the spring shoulder season, when there is far less competition for the homes you want to tour.
Run both numbers before you sign. The longer lease is not always right, but it is right more often than people expect.
Timing: what to do, and when
Now through September. Define your search area and lease term. The most desirable seasonal inventory in Boca Raton, Delray Beach, and Highland Beach is committed well before the season starts, and the January–March peak prices above the November and April shoulders.
October–November. Sign your lease and, separately, get your purchase financing pre-underwritten. If you plan to buy a condo, start the association due diligence education now — reserve funding, milestone inspection status, and lender approval status drive whether a building is financeable at all.
December–February. Live here. Tour actively. Note that single-family homes went under contract in a median of 41 days countywide, while condos took 69 — so the pace of decision-making differs by product type.
By March 1. If you have closed on a home and intend to make it your permanent residence, this is the Florida homestead exemption filing deadline. You must own and occupy the property as your permanent residence as of January 1 of the tax year, and file by March 1; missing the date waives the exemption for that year.
A word on residency
Florida has no state income tax and no day-count test of its own. The 183-day rule people talk about belongs to the state you are leaving — New York, New Jersey, Illinois and others use it to decide whether they can still tax you. Domicile is a question of fact, and a Florida driver license or filed Declaration of Domicile helps establish it but does not create it on its own.
Talk to your own tax advisor before you plan a season around a day count. I am a broker, not a tax professional, and the state testing your residency will be your former one.
Where to start
If you are weighing a season here, start with two lists: the communities you want to live in, and the ones you would buy in. They are often not the same, and knowing the difference before you sign a lease is most of the value of renting first.
You can browse current seasonal and annual leases, see what’s for sale, and read our community profiles for Boca Raton, Delray Beach, and Highland Beach. If you already own here and are considering selling into the season, start with a home valuation — or just reach out and we’ll talk it through.
Frequently asked questions
Should I rent or buy first in Boca Raton?
For most first-time seasonal residents, renting one season first is the lower-risk path. Boca Raton, Delray Beach, and Highland Beach differ substantially in daily lifestyle, carrying costs, and insurance profile, and a season on the ground reveals differences that listing photos cannot. Buyers who already know a specific community well can reasonably skip this step.
When should I book a seasonal rental in Boca Raton for the 2026–2027 season?
Late summer and early fall. The strongest inventory for the January–March peak is typically committed months in advance, and peak months price above the November and April shoulder periods.
Do I pay tax on a seasonal rental in Florida?
Yes, on short stays. Florida applies 6% state sales tax plus any county surtax to rentals of six months or less, and Palm Beach County adds a 6% Tourist Development Tax. Rent under a bona fide written lease for continuous residence longer than six months is exempt from the state tax.
What is the housing market like in Palm Beach County right now?
As of July 2026, the single-family median sale price was $660,090 (up 7.64% year over year) with 3.7 months of supply, and the condo median was $312,500 (up 3.99%) with 6.7 months of supply. Countywide active listings were down 21.1% year over year, and cash accounted for 47.7% of closed sales.
When is the Florida homestead exemption deadline?
March 1. You must own and occupy the property as your permanent residence as of January 1 of the tax year and file by March 1; failing to file by that date waives the exemption for that year.
Information deemed reliable but not guaranteed. Market statistics reflect July 2026 Palm Beach County data and change monthly. Nothing here is tax or legal advice; consult your own professionals.