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When booking a trip to a city you’ve never been to before, it’s easy to first look at the hotel chain you’re the most comfortable with. That may be because you have some sort of status with them or maybe you have a bunch of points in a loyalty program that you want to use. If this is your one and only search criteria, you’re doing yourself a huge disservice.

Note that I’m not saying chain properties can’t be nice; they can be very much so. In fact, sometimes a chain hotel can be the best hotel in town. It’s just that if you NEVER search beyond that, you’ll potentially miss out on some wonderful places to stay.

Key West, Florida has many independent hotels and because they’re smaller, they can be tucked into the blocks just off Duval St. There are a few major hotels in the tourist corridor that have the million dollar sunsets, but many of them are on the other sides of the island, far away from where you’ll probably want to be spending much of your time.

While not a comprehensive list, here are our opinions on which type of hotel we prefer to stay at when we’re in Key West.

Chain Hotels

Hyatt Centric Key West Resort and Spa

I wrote about our stay shortly after we returned home and I focused mainly on the room and the value for what we received. There were several things to like about the hotel. The location was wonderful and you could watch wonderful sunsets from lounge chairs on the sand of the “beach” or from a hammock on the end of the boat dock.

While the staff was pleasant, the experience was a bit sterile. They had a concierge booth that looked the same as what you’d see on Duval St., trying to sell you a boat cruise or trolley ride. While the hotel was pretty full, the vibe was pretty dead and we didn’t see more than a handful of people there for our whole stay.

The self-parking costs $29 a night (and premium spots cost $35) and they charge a $45 daily resort fee on top of the usual room rate.

We did enjoy our stay here and being able to redeem Hyatt points for the stay allowed us to visit the Keys when it would have been too expensive to go otherwise.

Crowne Plaza Key West – La Concha 

The La Concha hotel on Duval St. was opened back in 1926.  Now branded as a Crowne Plaza, it is part of the IHG hotel family.

We stayed here in 2014 while the hotel was undergoing a major renovation, and I somehow managed to not take any pictures of the hotel. I generally have no problem with a hotel doing renovations but it was off-putting that there was no mention of the pool being closed, the front entrance being blocked and the roof deck being turned into a spa anywhere on the website or booking confirmation page. To make matters worse, they were bringing all of the supplies to the roof by way of an elevator constructed on the outside of the hotel, and it was right outside our room. It was one of the only times I’ve complained to the manager of the hotel while we were still trying there and, to their credit, I was immediately refunded half of the points I used for the stay.  Here’s what I said on Facebook:

Here’s a video of the view out of the hotel window we had for our stay.

 

Now that the renovations are long finished, I’d consider staying here again. The hotel has a good location on Duval St. but the best feature of the hotel, the roof deck, was turned into a spa. I’ll miss watching the sunset from that deck.

The La Concha charges a $43/night destination fee which includes on-site parking.

Casa Marina Key West, Curio Collection by Hilton

When we stayed at the Casa Marina Key West, it was branded as a Waldorf=Astoria. While the hotel is a stunning example of the old Key West, it didn’t really fit and I’m glad that Hilton rebranded it as part of the Curio Collection.

The hotel is on the southern side of Key West which is close to the Southernmost Point, but not close to many of the tourist activities. It’s up to you to decide if this is positive or negative.

Guests pay an additional $45 resort fee and valet parking costs an additional $35 per day.

Independent Hotels

Marquesa Hotel

This was the first hotel Sharon and I stayed at together in Key West. I found a really good rate and it was totally dumb luck, as I didn’t know anything about the place before staying there. Our room was very nice but lacked a desk, a feature that someone who uses a computer even while on vacation finds to be an important feature.

We returned again a few years later and I called to ask the front desk if we could have a room with a desk. They went over all of the room types (i.e., one had a large desk but only a tub and another one had a small desk and chair but only a walk-in shower). We ended up with a room in the main building on the second floor that was very quaint and pleasant (and had a desk). We even got a nice welcome basket and a note as returning guests.

The hotel isn’t cheap (it cost $270 a night in 2010) but it mixes the Key West vibe with laid-back elegance. The buildings are all refurbished 1884 conch houses surrounding two pools. Also, no children under 14 years old are allowed to stay at the hotel. It is a quiet oasis just a few blocks off the hubbub of Duval St. I’d stay there all the time if it wasn’t so darn expensive. Unlike the chain hotels, this hotel has free parking for guests.

If you stay here, they can also get a reservation for you at Cafe Marquesa. I wrote about our meal there in my article about our favorite places to eat in Key West.

Eden House

By the time of our second trip to Key West, we had talked to several friends who had stayed there before and were told to check this place out. I can say that of any hotel that we have stayed at, Eden House captures the Key West atmosphere the best of all of them.

This is not a luxury hotel. There are hammocks around the property and a nice pool surrounded by palm trees. Rooms have no clocks and no radio (on purpose) and they offer fresh ground coffee and tea in the lobby 24/7.  They have board games and a guitar for guest use, as well as bike rentals.  They also have limited off-street parking (from their website: “We have about twenty spaces of off-street parking and about forty rooms. So, it’s first come first serve, folks. There is quite a bit of parking in the neighborhood and [worst case scenario] a garage a couple of blocks away”).

I think the write up on the complimentary happy hour will show the kind of hotel this is:

“Happy Hour is not to get you drunk or make you fall in love with us. It is there for a toddy or two at the end of the day, meeting some of our great guests, and getting ready for another fantastic night in Key West.

Our bar includes rum, gin, vodka, orange juice, cranberry juice, tonic, soda water, pepsi & diet pepsi, red & white wine. Of course, we offer only the finest inexpensive liquor.”

The Waldorf=Astoria it ain’t. However, we’ve stayed here twice and would do so again. The major drawback for us is that it is several blocks off of Duval so it’s quite a walk to get back to the hotel.

Unfortunately, we received an email from Eden House several weeks ago that, after having the same owner for decades, they’ve sold the property and it will soon be under new management.

Hybrid Hotels

This is a new category that I’ve created for smaller properties that are part of a large chain. The best example of this is the Kimpton Key West locations which are the size of the independent hotels yet bookable with IHG points.

Kimpton Key West Ridley House

I loved our stay at the Kimpton Key West Ridley House. We had a second-floor room with an outdoor sitting area. I spend a morning sitting by the pool while getting some work done before heading out for the day. The only downside was the mediocre breakfast, which may have been due to the pandemic.

A lack of parking was a minor annoyance but there was a reasonably priced lot around the corner that allowed overnight parking. It wasn’t cheap at 60,000 IHG points a night but that’s cheaper than the price they were charging revenue guests.

The Saint Hotel Key West, Autograph Collection

We’ve never stayed here but it fits in the hybrid category. With only 36 guestrooms, it has the feel of an independent but is part of Marriott Bonvoy.

Every time we’ve looked, the hotel’s been fully booked.

Final Takeaway

Previously, we enjoyed our stays at independent hotels more than the chain properties in Key West. As hard as the chain properties tried, they couldn’t capture the spirit of Key West, which is distinctly non-corporate. If we’re going to the Keys, we want the full experience and the independent hotels provide that with features like free parking, bike rentals and happy hour.

Now the lines are getting blurry. Independent owners are selling to corporate buyers who are incorporating the smaller properties into their portfolios. The addition of new brands which allow properties to be unique allowed this to happen.

Where will we stay the next time we visit? Since we don’t make plans for Key West very far in advance, the smaller hotels can sell out. If that happens, we’ll look to the large chain properties to see if there are rooms available for cash or with points. After all, any trip to Key West is better than no trip to Key West.

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