Buying a second home in Southwest Florida goes best when you price a full year of ownership, not just the purchase price. A winter home here carries costs a Florida homestead doesn’t, and the association’s rules shape how you can use it. Here’s the order I walk snowbird buyers through, from the tax bill to the drive home in April.
What does a second home in Southwest Florida cost to carry?
Plan on paying property tax on the home’s full assessed value, along with insurance and association fees, without the breaks a full-time resident gets. That gap is the biggest surprise I see with second-home buyers.
Florida gives the homestead exemption and Save Our Homes cap only to a permanent residence. A second home gets neither. It’s reassessed to market value when you buy it. After that, its assessed value for non-school taxes can rise by up to 10% a year, while school levies aren’t capped (Lee County Property Appraiser, 2026).
| Cost line (2026 rules) | As a second home | As your Florida homestead |
|---|---|---|
| Homestead exemption | None | Up to $51,411 off non-school value, $25,000 off school value |
| Yearly cap on assessed value | 10%, non-school taxes only | 2.7% for 2026 (Save Our Homes) |
| Citizens yearly rate increase limit | Up to 50% for non-primary homes | 15% for primary residences |
| My Safe Florida Home hardening grants | Not eligible | Eligible if the home and income qualify |
| CDD and other non-ad valorem charges | Owed in full | Owed in full, homestead doesn’t reduce them |
Sources: Lee County Property Appraiser, Florida DOR, Citizens, My Safe Florida Home.
Don’t budget from the listing. In my June 2026 video, I described buyers who saw a $4,200 tax bill on Zillow, wrote offers using that figure and learned at closing that the real number was about $8,000. The seller’s bill reflects the seller’s exemptions, not yours.
Community charges come on top of that. In the same video, I put a typical CDD assessment at $1,500 to $4,000 a year on the tax bill. HOA fees for single-family homes in master-planned communities can run from $200 to $1,500 a month, depending on what’s included (watch it here).
One change is pending. Amendment 3 on the November 3, 2026 ballot would cut the 10% cap on non-homestead property to 5% starting January 1, 2027. It needs 60% of voters to pass. As I write this, it’s a proposal, not law (Florida Senate).
What does insurance on a Florida second home depend on?
Mostly on the house. Roof age, impact protection, flood zone and the carrier you land with will move the premium more than the city name on the policy.
The market has improved. Citizens, the state-backed insurer, cut its average homeowners multiperil rate by 8.8% for 2026 (Citizens). But Citizens treats second homes differently. A non-primary residence can see its rate rise by up to 50% a year, while a primary residence is held to 15%.
Florida law requires insurers to offer discounts for wind-resistant features such as roof-to-wall connections and opening protection. You document them with a wind-mitigation inspection on state form OIR-B1-1802, which stays valid for up to five years if nothing material changes (Florida OIR). Ask the seller for theirs.
Flood is separate. Standard homeowners policies generally exclude it, and a federally backed lender will require flood coverage in A and V zones (FloodSmart). Keep these two dates in mind:
- Starting January 1, 2027, every Citizens personal residential policy that includes wind must also carry flood coverage at least equal to the dwelling limit. Condo unit (HO-6) policies are exempt (Citizens).
- The National Flood Insurance Program was authorized through December 11, 2026 as of late September 2026. Check FEMA’s reauthorization page before you close.
A seller’s existing flood policy can often be assigned to you. It’s worth asking about on any older home.
Can I rent out my Southwest Florida second home when I’m not using it?
Often, yes. But the association usually decides how. Check the rules before you fall for the house.
In our October 2025 buyer Q&A, I explained how widely the rules vary. Some gated communities allow perhaps four rentals a year, with 30 days between them. Some condos allow weekly stays, up to 52 a year, with a week between. A city or county can also restrict short stays outside any HOA (video). My short answer in that video still holds: if the home fits what renters want, it rents. The rules decide how often.
Jarrett sees the 30-day minimum more than any other restriction. In his September 2026 video, he covered other limits he runs into, including 90-day and one-year minimums and caps of three, four or 12 leases a year (video). In a golf community, ask what renters can and can’t use. Our July 2026 golf video covers that issue along with tee-time access in season (video).
Rentals of six months or less owe tax on the rent:
- Lee County: 6% state sales tax, a 0.5% county surtax and a 5% tourist development tax, 11.5% in total (Lee Clerk).
- Collier County: 6% sales tax plus a 5% tourist development tax (Collier Tax Collector). Collier voters decide on November 3, 2026 whether to raise the tourist tax to 6% starting January 1, 2027 (Gulf Shore Business).
Ask your CPA how rental income will be taxed at the federal level.
How is a second-home mortgage different?
Expect somewhat higher pricing and fewer program options than you’d get with a primary-residence loan.
In our July 2026 video, lender Paul Godbout of New American Funding explained two differences. Some owner-occupied programs that discount rates or closing costs won’t be available. Fannie Mae and Freddie Mac also add loan-level price adjustments to second homes based on your down payment and credit score (video). As discussed that month, rates ran from the high 5s to the low 7s depending on the program. That was a snapshot, not an offer. Talk to a licensed lender about your situation.
Should a snowbird buy a condo or a house?
A condo feels simpler. The fees can say otherwise, so compare a full year of costs side by side.
When Jarrett and I discussed this in August 2026, we used Bonita Bay as the example. Fees ran about $35,000 a year for some high-rise condos, compared with $4,000 to $6,000 for single-family homes in some of the community’s neighborhoods (video). People pick the condo so they never have to replace a roof. A couple of years of that fee difference can pay for one. Many HOAs here include lawn care, while a pool service can handle the pool and home watch can cover the rest. Golf adds its own layer, and how bundled, equity and pay-to-play clubs differ changes the annual bill.
We agreed on one real case for a high-rise, though. The view.
If you buy a condo, the paperwork matters more than the finishes. For resales, the seller must give you the building’s milestone inspection summary if one applies and its most recent structural integrity reserve study, or a statement that none exists (s. 718.503). I also ask for the last three years of association financials before my buyers write an offer. If a building can’t produce a clean reserve study and those financials within a couple of days, that tells you plenty.
When is season, and when do snowbirds arrive?
Season runs from late October or early November through April. January through March is the busiest stretch.
Lee County counted 1,004,200 visitors from January through March 2026. About 42% came from the Midwest and 26.5% from the Northeast. Another 8% described themselves as part-time residents (Lee County VCB). Traffic gets heavier and restaurant waits get longer during those months, something I covered in a 2025 video on Estero. Atlantic hurricane season runs from June 1 to November 30 (NOAA NHC), so a second home often sits empty during the riskiest stretch of the year.
Could my second home become my Florida residence later?
Yes. Homestead depends on where your permanent residence is on January 1, not how many days you spend here.
You need title to the home, and it must be your permanent residence as of January 1 of the tax year. The filing deadline is March 1. Neither you nor your spouse can hold a residency-based tax benefit in another state (Lee County Property Appraiser). The appraiser can consider a Florida driver license, vehicle registration, voter registration and the address on your federal return (s. 196.015).
Amendment 3 would treat people who were permanent residents by December 31, 2026 differently from those who arrived later. It’s a proposal on the November ballot, and I wouldn’t build a move around a proposal. Your home state’s residency rules matter just as much. Bring a CPA or estate attorney into the decision. My hard truths about moving here cover the tax picture for full-time movers.
Who looks after the house when you head north?
Usually, it’s some combination of your HOA, pool service and a home watch company. Home watch is common down here, and it’s cheap compared with the problems it can catch.
Someone checks the house on a schedule to make sure the AC hasn’t quit and nothing is leaking. Pair that service with a smart thermostat you can check from up north. If low upkeep is the priority, start with the HOA and amenity communities, where the lawn and common areas are handled for you.
How do you get back and forth each season?
Southwest Florida International (RSW) in Fort Myers lists nonstop routes to Chicago, Detroit, Minneapolis, Cleveland, New York, Boston and Philadelphia that aren’t flagged as seasonal. It also lists seasonal service to smaller cities such as Madison, Grand Rapids and Burlington (Lee County Port Authority, September 2026). Punta Gorda (PGD) fills some gaps.
If you’d rather bring the car, Amtrak’s Auto Train leaves Lorton, Virginia at 4:00 p.m. and arrives in Sanford, Florida at 8:59 a.m. the next day (Amtrak). From Sanford, it’s about four hours to Naples.
To compare what communities cost to carry for a full year, start with our community guides or browse homes. Then call Jarrett or me, and we’ll run the numbers on the ones you like.
