Where to Stay for a Key West Wedding: Old Town, Resorts or Rentals

The three lodging patterns for a Key West wedding weekend, what each does to your transport budget, and which one your guest list actually calls for.

By Michael Willis · Last reviewed 2026-09-10.

The question underneath the question

Couples ask where to stay. What they are usually asking is: how do fifty people get from where they sleep to where we are getting married, and what does that cost.

Key West answers that better than anywhere else in the Keys, because it is the one place in the chain where the answer can be "they walk."

The three patterns

Old Town guesthouses and small historic inns. Walkable to almost everything, including most ceremony sites and nearly every bar your guests will end up in. Rooms are individually shaped, which is charming and also means a fifty room block across one property is rarely possible. Expect to spread guests across two or three properties within a few streets of each other. Transport cost approaches zero.

Larger resort properties. One address, one block, one point of contact, a real function space, and usually parking. This is the pattern that makes a room block straightforward and the welcome party easy. The trade is that some sit outside the walkable core, which puts a shuttle back into your budget.

Vacation rentals and villas. Best for family groups traveling together and for the people staying longest. Worst for a room block, because there is nothing to block. Key West regulates short term rentals tightly, so confirm any property is legally licensed for the length of stay you are planning before anyone pays a deposit.

Most Key West weddings end up as a mix: a block at one or two properties for the bulk of the guest list, a rental for immediate family, and a handful of people doing their own thing regardless.

What it costs

Key West runs at the top of the chain's range rather than the middle of it. Against a Keys-wide average of $345 a night for the 2025 fiscal year, both the small historic inns and the larger resorts price above that more often than below.

The gap between April 2026 at $419.72 and June at $290.13 is wider than the gap between a guesthouse and a resort. Season is the bigger lever than property type.

On our three night planning assumption, two guests sharing a room spend roughly $520 to $630 per person on lodging before anything else. Add about $140 per person per night of non lodging spend, per the Monroe County TDC visitor study, and average airfare into Key West of $387 per the Bureau of Transportation Statistics, and a Key West guest lands around $1,200 to $1,400 for the weekend.

The transport question, answered properly

Key West is roughly four miles by two. Old Town is smaller than most people expect and genuinely walkable.

That matters to your budget in a way nobody mentions. If your ceremony, your reception and your guest rooms all sit inside Old Town, your transport line is a few golf carts and some taxis for the people who need them. If any one of those three sits outside it, you are chartering shuttles, and shuttles in Key West are priced for a town with limited vehicles and a lot of weddings.

Pick the lodging around the venue, not the other way around. It is the cheaper mistake to avoid.

Timing

The constraint in Key West is not really the calendar, it is arithmetic. Very few properties can absorb fifty rooms, and the ones that can are also hosting somebody else's wedding that weekend. That is why Old Town blocks tend to be split across two or three addresses within a few streets rather than held at one.

Before you sign anything, read [the room block guide](/guides/florida-keys-wedding-room-block). The contract terms are where the money is.

Where we fit

We are entertainment and production, not a planning agency, and we do not sell planning packages or act as your coordinator. The lodging side runs through an independent travel advisor affiliated with Fora Travel: property shortlists matched to your group, block terms explained before you sign, guest booking links, and the ground transport that follows from wherever your guests end up.

Figures from Tourism Economics, Smith Travel Research, the Monroe County Tourist Development Council and the US Bureau of Transportation Statistics. Published averages, not quotes. Short term rental rules are set by the City of Key West and change; confirm licensing directly.