This is another year we returned for a week in February. The location is perfect & the hotel is brimming with elegance and charm. We valeted our car with in and out privileges; i was easy as was check in when we were handed champagne. We are in room 254 an immaculate king room with a view of the entrance and gulf. Our room was quiet, the bed was comfortable, the water was hot and the air-conditioning worked well. We have a refrigerator, ceiling fan, coffee maker, and welcome gift containing sunglasses, champagne, popcorn, and a Fenway candle. We have vouchers for breakfast and morning coffee is in the restaurant. The Fenway Hotel, Autograph Collection is exactly like nothing else. For over 90 years, this hotel in Dunedin has welcomed the world's most celebrated artists & luminaries. A Jazz Age landmark, Dunedin, was home to the county's first radio station, and reminders of its musical past exist around every corner. It's located near Clearwater Beach, with unique hotel rooms & suites featuring amenities like fast Wi-Fi and pillowtop bedding. Brunch at the HEW Parlor and Chophouse, & sunsets at the Hi-Fi Rooftop Bar are memorable. read more

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I love everything about this hotel! I love the lounge areas, the friendly staff, the fantastic location walkable to downtown Dunedin, the view from the lawn and upper floors. The rooms are small but quaint. I will be back again! read more

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We have stayed at this hotel when friends from up north visit in the area. This time the gym was well ventilated as opposed to last year. Our room 254 overlooked the water. Customer service is exceptional as is the charm of the building. We got complimentary champagne upon checking in. There is live entertainment at 6pm as well as a rooftop bar that is usually crowded a little before sunset. After sunset, most left. Our room was comfortable for the 2 nights we were there. Also valet parking is available and basically a must since there is no parking in the immediate area. read more

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What can I say...we could not be more fortunate that this little gem is our local pub! Always a subset to remember, great service and great bar tenders!! All thumbs up!! read more

I e had a work event here by the pool. Very nice venue, good food and drinks. Enjoyed the atmosphere of old and new. And the water views and sunsets are amazing! read more

I love this historic hotel which is walking distance from downtown Dunedin. The rooftop bar is by far our favorite sunset view over the water. read more

Fenway Hotel, Autograph Collection - Rooftop sunset view from the Fenway Hotel - Hotels Near Me - Dunedin, Florida

Andrew was our server. He was enthusiastic and seemed genuinely interested in our experience. We had a great view of the sunset and everyone cheered when the sun hit the horizon! Very sweet moment! The drinks were pretty meh, I wish the espresso martini would have wowed us. The gin and tonic was weak. But the view was magnificent and Andrew sure gave it his best! read more

We had a wonderful stay at the Fenway! We were celebrating our 20th anniversary. There was complimentary champagne when we checked in which was a nice touch. The staff were very welcoming and helpful in every area of the hotel. We had dinner at Hew restaurant inside the hotel the first night and the food was excellent. We enjoyed watching the sunset from the rooftop bar every night. There was a jazz musician who played in the lobby/lounge area in the evening. She was excellent. We really enjoyed listening to her. We loved the short walk into Dunedin. There are plenty of restaurants and shops in town. We would definitely recommend and hope to be back again. read more

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Super cute hotel, well kept and has a jazzy vibe to it, very much Dunedin. It is located two blocks away from Dunedin downtown. Our room was small but very clean and cozy. Check out the rooftop bar and enjoy dinner at HEW Chophouse, - one of the best restaurants in town (we loved their seafood beignets and baked brie). read more

Fenway Hotel, Autograph Collection - Dinner at HEW - Hotels Near Me - Dunedin, Florida

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Tried to stop by for drinks but there was only valet available even though the rooftop bar was mostly empty.

Had dinner on January 22 2026.was the worst steak and lobster I have ever had first taiil came 5 minutes after my steak cam out .it was under cooked so I ask to just have it cooked for another minute o two instead they make me a new one that had a very strong formaldehyde taste .had stomac issues all night. Safe to say I won't be spending 300$ for a terrible dinner ever again at this restaurant. ZERO STARS read more

Fenway rooftop is an event at sunset but please add more bartenders. truffle fries are good

We stayed at the Fenway for just one night, but had an incredible time and definitely look forward to going back. The architecture was beautiful, the pool with thr lounge chairs and umbrellas was super cozy and we especially loved our evening with Terry at the bar! If you stay here I recommend checking out the rooftop bar and also taking a trip to Honeymoon Island State Park read more

Fenway Hotel, Autograph Collection - Relaxing afternoon at the pool at Fenway Hotel. - Hotels Near Me - Dunedin, Florida

Great hotel about a 15 min walk to downtown Dunedin. Room was comfortable and the staff was all beyond helpful. Decor around the hotel is excellent too. Rooftop bar is great especially at sunset as it has amazing views! read more

Fenway Hotel, Autograph Collection - Hotels Near Me - Dunedin, Florida

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Absolutely beautiful venue right on the water! You can't beat the views here. Gorgeous historical style hotel with modern ambiance and decor. I was here for a wedding in October, which was stunning!! We came for Sunday brunch with friends and ate at the restaurant downstairs. I was happy they had vegan options (milk for the coffee and a delicious oat bowl). Although they didn't have bottomless mimosas, we ordered a couple of bottles with OJ for the table. Lovely space and amazing service. Highly recommend! read more

Fenway Hotel, Autograph Collection - Oats brunch (vegan) - Hotels Near Me - Dunedin, Florida

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I thought the place would be charming, but it wasn't. Seemed kinda sparse, especially for the price: No real lobby to sit away from others to enjoy a cocktail (too small), pool area wasn't as furnished for lounging around as I expected. It is valet only, which was annoying, but they were quick. I didn't see any name tags so I wasn't sure about who worked here. The room was tiny, the bed reading "lamps" didn't work, there were ants in our bathroom and the glass sliding shower door was soooo hard to move it was almost comical. Finally, the AC was kept at 65 but it was most definitely not 65. Felt like 75 in there. I will try another hotel in the area next time. read more

This is an old historic building granted but it was purchased and totally refurbished by Mainsail and they are not known for cutting corners. I live locally and have attended functions in this facility since it first opened as a boutique hotel. I was impressed early on with what they accomplished, the food , ambience, upscale interior with piano bar etc . The only complaint I ever had was the absence of parking and being forced to use the valet ( which is still an issue). Unfortunately over not that many years this facility has to put it mildly has fallen into disrepair. The previous reviewer was correct in that it smells musty but that's generous. It reeks of mold. The bathrooms on the main floor are disgusting . I have not actually stayed overnight so I cannot comment on the rooms and for all I know they may be better. In terms of the food served to me during the functions I have attended I would also give that 2 stars. If I were Mainsail I would be having a serious sit down with whoever is managing this hotel. read more

This Hotel is a gem in Dunedin Florida. Rooftop bar, lovely Spanish style, with a wonderful pool in the middle. The staff and management are just outstanding!! Every single time we interact with the staff, they are welcoming, well spoken and extremely efficient. This is the hotel that you want to stay if you are looking for an experience. Not just a room. This Hotel is the whole thing. Come see for yourselves this incredible hidden gem overlooking the ocean from the balcony of the rooftop or having a bite Al fresco at the entrance. Next to the wonderful landscape gardens read more

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I'm shocked about the other reviews. Because of those, we had high expectations only to be extremely disappointed with everything. We paid OVER $600 for one single night and this is what happened: First, the so-called store had a few shirts and hats and some ridiculous toys. No snacks, toothpaste or anything else you'd expect in a hotel store. Rooms were small. My husband felt like we were in a motel six. And this was a surprise. This was Valentine's Day. They had two different performers on Monday and Tuesday, but not on Wednesday, Valentine's Day. HEW, their restaurant had a no-choice menu so you couldn't order off the menu. And, frankly, they had nothing u would eat. Both bars showed little interest in serving me. Jordan was on his phone at first and took forever to acknowledge I was even there. Upstairs , after probably 15 minutes, one of the many bartenders acknowledged me but that was it. I left. The lobby is smaller than any hotel I've ever paid over $600 for. The shower curtain rod was rusty. Damage to the bar chairs. I just expect so much more. Really no where to sit is the bar. We won't be back. To make matters worse, we were charged double and have to talk to the accountant about getting one charge back. read more

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This is not a review about the hotel. This is a review on Room 27. Group of friends and I went to the Halloween Spookeasy. Was cute, themed okay, and drinks were delicious. For a themed place like this that we don't have to go Orlando for, it's okay. Only complaint was that we paid $20 per person to get into the small room and when we got the menu there was no pricing on any of the drinks. Would have loved to know what we were in for. Also, there was no wine on the menu which was interesting as the drinks were topped with wine. The write up said there was ghost stories & the bar tender said " usually we have 12 people instead of 15". She gave one story after I asked her about it, but didn't seem spooky enough to pay $20 in the door and $20 per drink with a 2 drink minimum. Lame excuse for something we paid good money for. I did it, it was enjoyable, but will I be returning.... No. read more

From the moment we arrived Wen received the best treatment. The staff was welcoming and kind and really made us feel special. The rooms are clean and spacious with everything we needed. We'll definitely be back. Added bonus is the rooftop bar!! read more

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Nice hotel and staff. Very unique hotel. Wish upstairs bar was completed as that was one of the reasons we had booked this hotel.

This hotel is amazing. It's definitely not a place that you would bring your kids for a fun vacation. It's a great place if you're here on business or if it's an adult couple visiting the Tampa or Clearwater area. I was upgraded to a suite. Room 269. It was clean and comfortable and everything I needed. Decorations are cute, colorful, and well appointed. I had lunch at the restaurant downstairs, and the chef had a special gnocchi, and it was fantastic and the perfect proportions. I didn't know that the reservation that I booked included to drink vouchers, which were great to use by the pool during the day. The hotel is right across from the bay and you can see Clearwater Beach and honeymoon Island. The walking trail that is a block behind the hotel is fantastic and shaded. It was perfect for my morning walk. I decided to walk to Dunedin and check out the shops. It's a great funky town and it's about a 10 minute walk from the hotel. When I arrived back at the hotel, after my work about last night, they had live music, which was wonderful. I think most importantly, the service has been second to none. I travel for work almost every week, and it's hard to find great service. The staff is attentive, kind, and professional , and they go out of their way to help you. This includes everyone from the bartender to the valet. I didn't think that I would like staying here because there is no beach. But this was beyond what I imagined. read more

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The Fenway is the best hotel to stay at if you have business in Dunedin, Clearwater or Tarpon Springs. It's local vibe, live music, along with great food and drink make a special place to stay. Pro Tip: Ride their bikes to downtown Dunedin, or ask for them to setup Croquet on the front lawn. read more

Love this hotel! It is a Marriott property, but has such a local feel. Two blocks from the trail and looks at the ocean/beach! Pet friendly and absolutely exceptional service in all areas. The puppies and I LOVE this gem. read more

Rooftop bar, elevator up to the rooftop. Great drinks and entertaining bartenders!! Watching the sunset was great. read more

Fenway Hotel, Autograph Collection - Bar area - Hotels Near Me - Dunedin, Florida

The hotel is very cute and funky and had a very cool old vibe. Unfortunately, it's smelled like a musty attic. Very outdated not upscale at all and absolutely not worth the price. read more

When it comes to restoration projects, this hotel is truly an exemplary building. This historic jazz age property is a beauty. It's history began with its construction in 1924, it functioned as a hotel, as a private club and then, very recently, a hotel again. It's a neat property all around from a design standpoint. Restoration is quite good on the surface, but not luxurious or meticulous by any means. As far as recognition for Marriott elite status (ambassador in this case), it's fairly minimal. No upgrade, breakfast is minimal selections of only one item from the menu and no other perks. The breakfast of croissants and fruit was tasty and croissants very fresh, but when staying four nights, it gets quite old. The room didn't even have a view, unless one enjoys looking at air conditioning units. The hotel was not fully occupied, thus in summary, status is rather useless here. The rooms, despite being recently renovated, are very, very small. Certainly not Florida style rooms, but more comparable to what one would find in New York room. Design in most ways is pretty neat throwback to the times with a twist of contemporary modernism through brass and fixtures. The basics such as slippers and coffee maker were missing, but were brought to the room rapidly upon request. The headboards were detached from the bed, making it reminiscent of a motel as opposed to an Autograph Collection. Odd area to cut costs. In all other aspects of design, the room was very well appointed, with comfy bathrobes, South America inspired tile and Amazon Alexa. Service was excellent. Front desk always well staffed. Breakfast restaurant staff on point. Valet quick. So, summing up the Fenway is a bit difficult as it ultimately depends on the price paid. It is unique and sharp. It misses to hit the high points on status recognition and room size. It is conveniently located and cozy. read more

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It was a fabulous new dining experience and the roof top bar looks busy and great. Love the fact the rooms are wonderful would say they sure did make it a great renovation. read more

Fenway Hotel, Autograph Collection - Had dinner and it was wonderful! Great restaurant and wonderful service! Lovely place to be in Dunedin. - Hotels Near Me - Dunedin, Florida

Our first time at Fenway as a one-night staycation with family over thanksgiving to enjoy each other without distraction. Colton greeted us at check in and his friendliness set the mood for the next 24 hours. The staff are very proud to represent this historic building and all that Dunedin has to offer, including the view from hotel. It's a tradition for guests to enjoy 3rd floor HiFi rooftop Sunset together, with staff counting down and a guest clanging symbols at Sunset. The hotel is surrounded by activities that don't involve a car: Pinellas Trail is only 400 steps away ( we counted!): Downtown Dunedin and Marina just 3 blocks; and Dunedin Blue Jays Stadium is only 4 blocks. Honeymoon State Park is a short drive, but also connected to Pinellas Trail if biking. Croquet equipment at front desk for playing on the front lawn and bikes are free to check out. Building is 3 stories and updated to be ADA accessible, including pool and watching sunset at rooftop bar. All sidewalks from hotel to Pinellas Trail updated to ADA for crossing streets. Parking is by valet only as local street closed to guest parking. Check with hotel if you have multiple vehicles or guests visiting and need parking. If you are a Blue Jays spring training buff, stay at Fenway and never drive during your visit. Restaurants and local brewing pubs, all shirts and sandals casual, are plentiful and within walking distance of Downtown or on Pinellas Trail. As hotel is newly renovated, rooms are very clean and decorated with Scottish colors. Nightly free entertainment in lobby that is generally a jazz duet., with full coffee and liquor bar. The history of the building goes back to early 1920's, as it hosted first radio broadcast on rooftop for Pinellas County and has an exhibit showing entrance to the speak easy that was part of building. The Fenway is proud to incorporate local activities and non profit fundraising. As a local you can enjoy registering for a wide variety of social activities such as afternoon tea, group functions in meeting rooms, or learning to make your own 1920's cocktails. It boils weddings and other local events. Give it a visit just to check it out. read more

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Very nice place. Very pricey, prepare to be nickel-and-dime'd for the duration of your stay.

Character, history, and location makes this a pretty unique and good hotel. The Fenway has a 20's Speakeasy and jazz feel to it. And with that, there are some good and not so good aspects to this hotel. Service and front desk were friendly and set a good vibe. Bad part is that you will have to haul your luggage yourself from your car, up some stairs to the check-in desk, and then eventually to your room yourself. The valets and/or employees there will not offer this service. There is only one elevator for the whole hotel, so waiting can be commonplace when going to and from your room or other areas of the hotel. Exterior of the building is beautiful and so are the grounds. The Hotel is not right on the water or really has access to the water but it's close enough that you can get a view of the water (but also depends on your room itself). Rooftop bar is great and offers nice views of the water and property. But it can get very crowded early and/or at certain times. Rooms are decent. Sort of small and nothing special. But does have a few small touches that makes it nice and a step up from your standard hotel room. Should fill the mini-fridges in the room with less drinks. I think most people would agree that 20 different types of can and bottled drinks and water is really not needed. There was not enough room to put any of own stuff in there to cool off and/or stay fresh. Our baby food, our own drinks, leftovers, etc. could not fit and thus we had to remove some of the drinks and leave them on the counter. Created a mess and clutter on the drawer's countertop. Loved that the fan had a large fan to keep the room circulated. Would be nice if the bathroom had an exhaust fan (fart fan). Outside pool is smaller than what it looks like on the website. Nothing special here or any great views but overall not bad. Inside bar / Ground Floor - is convenient and has a nice setup. The middle-aged bartender when we were there was not friendly at all and very surly and kind of rude. But there is a music riser/stage near the bar that has some live music on certain nights. The hotel is close to downtown Dunedin which is a bonus. Close enough to bike there; which The Fenway has some bikes to rent onsite. read more

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David at the lobby bar recognized me and had my drink waiting even before I was seated. This is why I keep coming back. He also wears the best shirts! read more

This place was amazing! The band was awesome and the food and drinks were on point! The wait staff were hopping and on it! Add a bonus sky after the sunset! Ya gotta go!!! read more

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No hot water in faucet. No counter space in bathroom to put toiletries. Only one chair to sit in. So cold in the room we wore our sweatshirts and didn't want to get dressed for bed. We had a view of the cats in the parking lot even though we spent $400 per night. The bed is comfortable and staff is very responsive to our needs and complaints. Nice large Tv and full length mirror and closet. read more

What a fun, glamorous and gorgeous hotel! The hotel property has an old Hollywood feel to it which I absolutely loved! The staff was great getting us checked in with a complimentary glass of bubbly. The rooms were very clean, and comfortable. The pool area was also very nice with plenty of lounge chairs throughout the area. There are two restaurants on the premise, a rooftop bar with great views but a limited bar-food menu, and the chophouse with a more traditional dinner menu. I highly recommend the chophouse for both dinner and breakfast. If you feel like venturing off, the hotel has bikes you can rent, with the first hour free. There are lots of local restaurants and bars nearby you can walk or ride to. Weekends here tend to be very busy at the hotel, so expect crowds at the restaurant and rooftop bar. Lastly, the sunset views here are amazing! read more

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Rooftop Bar Atmosphere: great view of the water. Drinks: kinda pricey. I ordered the speakeasy sipper - A whiskey cocktail. It was good. I didn't know what to expect since, The drink description on the menu don't tell you what is in the drinks. All I know is what brand whiskey they used. Good selection of music. Even though they have food menus, they don't serve food on the rooftop. We were told we would have to go downstairs to the restaurant to eat. read more

Fenway Hotel, Autograph Collection - Speakeasy sipper - Hotels Near Me - Dunedin, Florida

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The 4 star is for the roof top bar!! I did NOT stay at Hotel. So my rating is basically based on what I saw of the view, the bar, and the entry way to Hotel and the grounds!! The view at the top is beautiful! Dunedin is a quaint, charming City. It's surrounded by water, nice restaurants and the Hotel is in a perfect location! Parking is in the back or you can valet. Nice set up at bar and friendly staff. If you have not been you need to check it out! read more

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Always great to start on the rooftop with a cocktail and to watch the sunset before dinner. Then downstairs for a fabulous meal. We like to sit at the counter and watch the chef in action. The food never disappoints! read more

You let me down tonight Fenway. We arrived at 7 pm for Oysters and Jazz. The event ran from 6-9. Oysters we're GONE! The "Jazz" was 70's pop although I will hand it to the saxophonist he has real chops. So we went in to the bar to have your classic burger which we've loved in the past. It was tasty and good BUT you forgot the cheese! Entirely! I'll think about whether we'll be back. Suggestion- if you're doing something on a holiday weekend expect a crowd, staff for it, and prep for it. Running out of the one thing you advertised not good. read more