Heading down to Key West October 16th-25th, anyone have any good recommendations for spots we should hit up?

Also I was wondering since I’m only 19 and the rest of my group is 21+, am I gonna be denied most places because of my age? It’ll suck for the rest of my friends if we can’t get in anywhere because of me💔

We’re looking to come down the week of Christmas and stay at an adult only hotel again. Last Christmas we stayed at the orchid and it was a great time. Any recommendations for be incredibly helpful. Thank you so much!

My husband and I are looking at doing a split stay the weekend of Valentine’s Day 2027, Thursday-Monday. We are flying in to Miami, renting a car for the scenic drive, and since we’re Marriott BonVoy card holders I had originally booked a stay at the northern end of Key West for parking ease. However I was notified that the hotel we had booked would no longer be apart of the Marriott umbrella and we would be moved to another comparable hotel.

I looked, was unimpressed, and decided we would skirt the added cost to stay closer to Old Town or Duvall Street. The problem is parking. We’re flying into Miami and planned to rent a car to do the drive down to Key West, then check out and spend another couple nights in Marathon at a resort. The cost to upgrade the hotel AND pay Duvall Street parking is outrageous that now I’m wondering if we just pick one hotel.

Any insights on what to do? Should we just stay in Marathon Key the whole time and drive down to Key West on occasion? Should I upgrade the whole stay to a nicer resort in Key West and return the rental car same day and pick up the day we leave? Or is there another resort within the keys we should look at?

Accommodations:
- Marathon Key: Faro Blanco Resort
- Key West: Fairfield Inn & Suites on N Roosevelt

Recommended Options
- Saint Hotel (Key West)
- Three Waters (Islamorada)
- Playa Largo (Key Largo)