A buyer I worked with last season stood in an unit at Carlysle, then walked three buildings north to a nearly identical layout at Windsor. Same price band, similar square footage, same walk to the same stretch of sand. She asked the obvious question: if she ever wanted to lease the place out for a season while she traveled, which building made more sense. The answer split the two properties in half. Carlysle allows one lease per year with a 90-day minimum. Windsor does not allow rentals at all, under any terms.

That is the piece of Bay Colony that does not show up on a listing sheet. The enclave reads, from the outside, like a single product: one gate, one beach, ten towers that all share the name. In practice it is ten separate condominium associations, each writing its own rules about what an owner is actually permitted to do with the unit once the closing is done. The address is the same. The fine print is not.

Ten Buildings, One Gate, Different Rules

Bay Colony's high-rise inventory runs to ten towers: Biltmore, Brighton, Carlysle, Contessa, Marquesa, Remington, Salerno, Toscana, Trieste, and Windsor. Six sit directly on the sand, running north to south as Remington, Windsor, Biltmore, Brighton, Carlysle, and Contessa. The other four, Marquesa, Toscana, Salerno, and Trieste, sit a block or two back from the water.

Rental policy is where the towers stop behaving like a single community.

Most of the tower associations converge on the same structure: a 90-day minimum stay, capped at one lease per year. That is already restrictive by short-term-rental standards, but it leaves an owner some flexibility if a future season calls for it. Windsor removes the option entirely. If you buy there, the unit is yours to occupy or leave vacant. There is no lease-back scenario, no seasonal income plan, no fallback if your own plans change.

Windsor's Rule Isn't a Footnote

This matters for reasons that go beyond convenience. A unit that cannot be leased at all is a different financial instrument than one that can generate even limited income. It narrows the buyer pool to people who are certain they will occupy the property themselves, which affects resale timing and, over time, how appraisers and lenders think about comparable sales in the building. Two units with the same view and the same price per square foot are not the same asset if one of them can flex with your life and the other cannot.

If a rental option matters to your plans, even as a distant possibility, that question needs to be asked and answered in writing before you're comparing floor plans. It should not be assumed from the fact that the building next door allows it.

The Number Trieste Can't Agree On

Trieste presents its own version of this problem, and it's a subtler one. Several sources describing Trieste's governing rules state that owners may lease their units twice a year, each for a minimum of 90 days. At least one other source describing the same building states the limit is one lease per year. Both cannot be correct for the same set of governing documents.

I raise this not to resolve it here, but to make the point directly: marketing copy and third-party building summaries are not the governing documents. If lease flexibility factors into your decision at all, the only reliable answer comes from the current condominium documents themselves, requested directly, not from a building's promotional page or a prior year's FAQ.

Density Sets the Dues, Not the View

A related pattern shows up in the fee structure across the ten towers. Buildings with lower unit density, Marquesa and Windsor among them, tend to carry higher per-unit fees. Buildings with more units sharing the same fixed costs, Trieste being the clearest example, land on more moderate dues. The logic is simple once you see it: a roof, a lobby renovation, or an insurance premium gets divided across however many units share the building, so a tower with fewer, larger residences spreads those costs across a smaller base.

That means the sticker price and the price per square foot only tell part of the carrying-cost story. Two towers at similar price points can carry meaningfully different monthly obligations once density is factored in, and that number belongs in the same conversation as the view.

The Address Doesn't Include the Golf Course

The most consequential thing a Bay Colony address does not automatically include is golf.

Every one of the condo associations confirms the same structure: ownership brings automatic membership in both the Bay Colony and Pelican Bay associations, which covers the beach clubs, tennis, and the broader amenity package. Golf is carved out separately, purchased on its own, at its own price.

Bay Colony Golf Club runs a tiered membership structure. A full Equity Golf Membership carries a $350,000 initiation fee and $25,400 in annual dues, capped at 300 golf members, with a no-tee-time policy that lets members play whenever they want rather than booking around a schedule. Below that sits a Social Awaiting Golf tier, at $75,000 initiation and $12,700 in dues, limited to five members at a time as the step just before a full golf slot opens. Below that, a Non-Equity Social Membership runs $30,000 initiation and $6,350 in dues, capped at 100 social members, granting clubhouse and dining access without golf privileges.

Here is where the picture gets genuinely inconsistent. A separate published profile of the club, dated February 2026, cites a $150,000 initiation fee against a $15,000 annual due, a figure less than half the equity tier described above. I'm not able to reconcile that gap from the sources available, and it's large enough that it should not be treated as a rounding difference. If golf membership factors into your purchase decision, the initiation number needs to come directly from Bay Colony Golf Club at the time you're ready to apply, not from any published guide, including this one.

There's a second layer worth flagging. The club's own membership page states that equity golf memberships are currently offered without residency restrictions, based on availability, meaning owning in Bay Colony is no longer even required to join. At the same time, buyer-facing sources describing the same club report an active waitlist for full equity golf slots. Those two things are not necessarily contradictory. A club can be open to non-resident applicants in principle while still running a waitlist in practice. But the gap between the club's own public framing and what buyers are told on the ground is exactly the kind of detail worth confirming with a direct phone call before you assume a timeline for getting on the course.

What This Costs in Today's Market

The numbers behind all of this are current. A market update published in early July 2026 put trailing 12-month sales across Bay Colony's six oceanfront towers at just 24 closed transactions, priced between $1.93 million and $10 million. That is a thin trading pool for an entire year, which is part of why the tower-by-tower differences carry more weight here than they might in a higher-volume market. When only two dozen units trade annually, the rules attached to each one matter more, not less.

The Strand at Bay Colony, the enclave's small run of single-family estate homes on the water, trades even less often, roughly once every year or two. Pricing there has ranged from $12.5 million to $19 million over the past decade, and as of a July 2026 market update one Strand property was listed asking $34,900,000, or $4,840 per square foot.

On the condo side, a recent transaction illustrates the pricing discipline this market rewards. A Carlysle unit sold for $3.4 million after sitting on the market for a stretch, closing only once the sellers adjusted their asking price, a deal reported by Naples Press in early July 2026. Even inside one of Naples' most sought-after enclaves, an unrealistic number sits unsold. Buyers here are doing their homework, and sellers who price to that reality are the ones getting to the closing table.

Three Things to Confirm Before You Write an Offer

1. Request the current governing documents for the specific tower, not the building's marketing page, and confirm the rental terms in writing.
2. Ask Bay Colony Golf Club directly whether equity memberships are open today or waitlisted, and get current initiation and dues figures rather than relying on any published figure, including the ones above.
3. Compare a building's unit density to its HOA and club fees before comparing its view to its price. The fixed costs behind the glass matter as much as what's on the other side of it.

FAQ

Does every Bay Colony condo include beach club access? Yes. Ownership in any of the ten towers carries automatic membership in the Bay Colony and Pelican Bay associations, which covers beach and tennis amenities. Golf is the exception, purchased separately at its own price.

Can I rent out my Bay Colony condo short term? No building researched allows anything under a 90-day minimum lease term, and Windsor does not permit rentals at all. If flexibility to lease matters to you, that needs to be confirmed tower by tower before you're under contract.

Is Bay Colony Golf Club accepting new members right now? The club's own materials describe equity memberships as open, without a residency requirement, based on availability. Buyer-side sources describe an active waitlist for full golf slots. Both can be true at once. Call the club directly for a current answer before you build a timeline around it.

If you're comparing towers in Bay Colony, or trying to figure out which set of rules fits the way you actually plan to use the property, I'd rather walk you through the current governing documents myself than let a marketing page make the decision for you. Karl Faerber works this market from Fifth Avenue South, and I'm glad to talk through what a specific unit does and doesn't include before you make an offer on it. Let's Connect.