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The Fenway Hotel: An Historic Jazz Age Boutique Hotel in Dunedin, FL

If you’re looking for a historic boutique hotel in a charming small town in Florida, I’ve got a place for you. This historic 1920s “jazz age” hotel is the perfect place for a quick weekend getaway.

Located right on the bay just a couple of blocks from historic downtown Dunedin, the Fenway is historic and chic but still modern and comfortable. 

Here’s a quick rundown of what I liked about staying at the Fenway Hotel:

It’s just about a 3-4 block walk to the main part of downtown Dunedin. You can walk along the water or through the neighborhood. If the weather is decent, it’s very walkable. If it’s hot, it feels FAR but they have bikes you can take. 

It’s right on the bay. There’s no beach in Dunedin, but the property sits right on the water. There’s a great view from the rooftop bar, but they also have chairs set up out front that you can sit out during the evening. 

It’s about four miles south of the Dunedin Causeway which is the entrance to Honeymoon Island State Park. Honeymoon Island and Caladsi is the big draw to Dunedin and honestly there aren’t a ton of places to stay. There’s a Holiday Inn about a mile or so north of the Fenway and then there’s a Hampton Inn right at the causeway. Either place you’re going to have to pack everything up in your car and drive to Honeymoon Island, so you might as well stay at the cool historic hotel closer to downtown. 

The brand is pretty strong. It’s a historic 1920s hotel built in the middle of the jazz age and prohibition and they really play that up. Everything from your room key to the bedside table lamps tie back to the music theme. They’ve even left the door to the original speakeasy intact in the lobby!

While the hotel feels very historic and original, it still has all the modern comforts and conveniences you’d want. 

The TV situation is excellent. This feels so oddly specific, and I hardly ever even turn on the TV when I’m in a hotel (I always have an ipad or laptop with me), but it was on the welcome screen when we arrived and I noticed it had a setup where you could login to your Netflix, Hulu, etc. But I was most impressed with all of the CHANNELS. I stayed here during the Olympics and they had pretty much every channel that they were showing the Olympics on plus a ton of specific sports channels (I have never stayed anywhere with the Tennis Channel in my life and I was in HEAVEN). They had a ton of non sports stuff too, and overall the TV situation made a huge impression on me ; ) 

For me, probably the best part of the Fenway Hotel is that it’s part of Marriott Bonvoy. It’s in their “Autograph Collection.” I’m pretty loyal to Marriott and I’m always trying to track and maximize points so I was THRILLED that this historic hotel in this area that there aren’t too many options happened to be part of Marriott. 

Pricing starts at $169. Check rates for your dates here.

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