*DIS Contributors review meals, resort stays, and entertainment that they have paid for during their own vacations. They only utilize discounts and offers if they are available to the general public, such as annual passholder discounts, Tables in Wonderland, or DVC membership discounts. They receive no additional compensation for dining experiences or events, so that they may give their honest opinions about price and value.

Old Key West Resort holds a special place in my heart, not only because it’s the first Disney Vacation Club Resort but because we stayed there all the time when I was younger. This resort is very nostalgic for me. I decided I wanted to have dinner at this resort for my birthday to feel the nostalgia and relive some memories. I hadn’t eaten at Olivia’s Cafe since I was very young, so I don’t remember my experience at this dining location. While walking to the restaurant, I saw that the resort’s lobby had been completely redone, and it’s gorgeous, and I wish they would renovate Olivia’s Cafe to look as clean and sleek as the lobby. 

Olivia’s Cafe gives off, I hate to say it, a tacky vibe with oversized nautical-themed decor. I do love all the photos on the walls of Disney Vacation Club members. These photos give the restaurant a more personal feeling, and it feels like a bit of a piece of history. I have heard many mixed reviews about the resort as a whole and Olivia’s Cafe. I want to start with the service. Our server Paul was fantastic. He paid attention to detail, he didn’t rush us, but he did not leave us unattended for long periods. He let us know the most ordered items on the menu: the Southernmost Buttermilk Chicken and the Slow-cooked Prime Rib. The day’s soup was the Loaded Baked Potato soup, and I love this soup from Chili’s, so I had to try it. I’ll be honest, I like the one from Chili’s better than the one at Olivia’s because it has more potatoes. For starters, we ordered the Crab Cake because I wanted to compare it to the one I had at Disney’s Vero Beach Resort. This crab cake was surprisingly delicious. The crab cake at Vero Beach was made with a different type of crab meat, Stone Crab, and the one here at Olivia’s was made with Blue Crab. This crab cake had barely any fillers, so it was all pure crab and tasted delicious. The crab cake comes covered in a jalapeño aioli sauce and pineapple slaw, which added some great flavor.

For the main course, I decided to order one of the less popular dishes, which is the Cayo Hueso Shrimp Pasta. This pasta dish has sauteed shrimp, zucchini, yellow squash, grape tomatoes, spinach, and penne pasta in a pesto cream sauce. I enjoyed this dish but be aware that the serving is huge. This plate could easily feed two people. Lucky me, I was able to take home leftovers for lunch the next day. I thought the pasta was good, but I feel like they could’ve put some more pesto in there because I feel like it was lacking that pesto flavor. My wife got the Southernmost chicken dish with mashed potatoes, green beans, and a biscuit. She devoured her meal and said it was delicious. She said that the chicken was the star of the show and that the gravy was a perfect dipping sauce for the biscuit. We were so full after the meals that we did not order dessert, but my mom ordered the chocolate martini they have as her dessert, and she said it was terrific. She said it was a perfect way to end her meal. 

Our server found out it was my birthday, so Paul sent me home with a fun birthday cupcake, which was very sweet of him. The service is what made this dinner better than it was. I wasn’t blown away by dinner, but I did think it was good; it just wasn’t out of this world. I am a firm believer that service can make a difference when dining, and Paul certainly made our dinner fun. Overall, I had a great time, and the food was good. I do think the restaurant needs to be renovated to match the vibes that the resort’s lobby gives off. The lobby had this beautiful blue accent color that I think would make Olivia’s Cafe look beautiful. They could keep the fun seaside Old Key West vibes while also making the restaurant look brighter and sleek. That is the biggest critique I have about Olivia’s Cafe at Old Key West. 

Let us know in the comments if you’ve ever eaten at Olivia’s Cafe!