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Built in 1924, Fenway Hotel is an icon of the jazz age. Throughout its time as an operating hotel, the Grand Lady of Dunedin has hosted explorers, artists, politicians, musicians and more. With walls echoing its musical heritage, the hotel earned a place in history by serving as the county's first radio station. It's by bringing these elements together that we create the new vision for Fenway Hotel and a destination unlike any other.

Guest Reviews

shawn carroll

3 weeks ago

The historic hotel is beautifully located to catch the west coast sunset from atop the roof top bar. Get there early or you will be standing. The bellhop, front desk and rooftop bar staff were just as pleasant as you can ask and the hotel spotless. We had a few drinks at the roof top with such great service then decided to walk down to the bar in the lobby, what a difference in service. The gentleman downstairs had a bit of arrogance and wasn’t very attentive. My wife and I sat outside on the front patio and wanted to order something small, so I went in to lobby bar and orders black truffle fries from the bar. 40 minutes after, we walked in to sit at bar and see if fries were ready. They said must have made a mistake and ordered again. A little over an hour (for fries) we had them pack to go. What we thought were black truffle seemed more like $12 salt and black pepper fries. The next morning we went down to have breakfast a little after 7:15. The young lady behind the Kitchen bar said to take a seat and they will be right out. 20 mins later my wife and I walked out because no one ever greeted or came to the table. This is a beautiful place to come and visit and is in a great location, but if you want exceptional service you need to get it from the rooftop bar or Bon Appetit which is about a block away. That’s the only place we found it

Mary Funkhouser

a month ago

Our room was beautiful and the view of the water was lovely. We went to the rooftop bar a couple of times and had a great experience both times. The location was perfect, it was a short walk to the biking/walking trail that takes you straight to downtown Dunedin. We're looking forward to our next stay!

Natalie Frazier

a month ago

We had our wedding welcome party at the Hi-Fi Rooftop at the Fenway Hotel, and it was the perfect way to kick off our wedding weekend! From the planning process to the event itself, everything exceeded our expectations. Ashley Havens was absolutely wonderful to work with. She was incredibly friendly, responsive, and made planning the event so easy. Her attention to detail and willingness to help ensured everything came together seamlessly. The rooftop atmosphere was beautiful, the food and drinks were fantastic, and our guests are still talking about how much they enjoyed the evening. The Fenway Hotel also provided the table centerpieces, which looked beautiful and made the space feel even more special. We couldn't have asked for a better venue for our welcome party. Thank you to Ashley and the entire Fenway Hotel team for helping us create such a fun, memorable evening for all of our family and friends. We highly recommend the Fenway Hotel for anyone looking to host a special event!

Anthony Coggins

a month ago

I have to travel to this area once a month and have been trying to find my preferred hotel - I've now found it. From the moment I arrived to when I left for my early flight, the staff were incredibly accommodating and the hotel truly deserves the Autograph Collection name for it's uniqueness and luxury feel. The rooftop bar is something you don't want to miss either! Amazing reviews and great selection.

Michael Berthiaume

3 months ago

We had a fantastic stay at the Fenway Hotel. The hotel is beautiful and full of character, and the staff was incredibly accommodating throughout our visit. We loved the rooftop bar, and brunch at the Parlor and Chophouse was excellent. Jaime, our waitress, did a great job and took great care of us. The saxophone player was a great touch and really added to the atmosphere. Would absolutely stay here again. Highly recommend!

Standard Amenities

Number of Rooms: 4

Total Square Feet: 5,000

Largest Room: 2,300

Sleeping Rooms: 83

Meeting room capacities
Room Square Feet Theater Classroom Banquet Reception
Scanlan 540 48 30 36 40
Fenway Front Lawn 7200 500 500
Private Dining Room 270 10
Caladesi Ballroom 2356 170 96 180 200

General Information

  • Family-friendly
  • Gift cards available
  • Hours: 24 Hours
    Complimentary Valet for restaurants & events, overnight parking fees apply.
  • LGBTQ+ Friendly
  • Paid parking on-site
  • Reservations suggested
  • WiFi available

Discounts

  • Florida Resident Discount
  • Group Discount
  • Military Discount
  • Senior Citizen Discount

Accessible Features

  • Accessible parking
  • Accessible restroom
  • Wheelchair lift or ramp
  • Wheelchair-friendly inside walkways
  • Roll-in showers
  • Wheelchair Accessible Entrance
  • Wheelchair Accessible Parking

Activities Offered on Site

  • Bicycle Rental

In-Room Amenities

  • Linens/Towels

On-Site Facilities & Services

  • Exercise/Fitness Facilities
  • Outdoor Pool
  • Picnic Area
  • Restaurant
  • Room Service

Property Details

  • Number of Suites/Condos: 18
  • Number of Units: 83

Vacation Rentals

  • Weekly Availability