Why We Have a Love-Hate Relationship With Disney World’s Worst Deluxe Resort

One of the hills that I’ll die on is that Walt Disney World’s biggest asset is not that it has 4 theme parks, more than double any other destination. It’s not the classic attractions, unique modern E-Ticket rides, or even the marquee new lands. It’s not the hundreds of restaurants, although we’re starting to get warmer.

Technically, what we love most about it is the Walt Disney World Resort complex as a whole. But that encompasses everything and feels like a cheesy answer, so we’ll narrow it down. The biggest asset of Walt Disney World that is distinct from other destinations is the over two-dozen resort hotels. These are widely varied properties, each with their distinct charm, selling points, as well as interconnectivity and transportation.

The argument could be made that other resort complexes do attractions better, despite only having one or two parks to Walt Disney World’s four. Many fans believe California or Japan have better ride rosters. What they do not have, however, is a better lineup of hotels. This is evident in the topic of today’s post, Disney’s Old Key West Resort, which is our least-favorite top-tier hotel at Walt Disney World. But before you bust out the pitchforks, hear us out!

We love every single Walt Disney World resorts and staying in the bubble. There is not a single WDW hotel we dislike. Literally. All of them have strengths and each brings something special to the table. What makes it the Vacation Kingdom of the World is the spaces between the theme parks; nowhere does it like Walt Disney World.

The one thing we miss most about no longer living in Central Florida is losing those weeknight visits to the resort hotels. Doing a very leisurely dinner and walking it off afterwards via a stroll around the resort while enjoy the atmosphere, and discovering something new.

We still visit often and do a lot of hotel stays, but that’s the one thing that just isn’t the same. Being a local with all sense of urgency removed is transformational in how you experience the resorts. If there’s one reason to choose Florida when ‘moving to the magic,’ it’s that. Not the parks. But I digress. 

I say all of this as a preface because every list ranking rides, restaurants, or even resorts ends up being controversial or contentious is because of subjectivity and sentimentality. While there is consensus that Pirates of the Caribbean is superior to Beauty and the Beast Sing-Along, some people will prefer the latter.

Same goes for resorts. Many longtime fans have a “home” hotel where they always stay and have fallen in love with over the decades. And unlike rides or restaurants, as discussed above, all of the resorts are varying degrees of good or great.

Dubbing anything the “worst” is courting controversy. Worst is a relative term, and could still be great. A hotel with a guest satisfaction score of 88% (made up number) is still respectable, but could its counterparts with numbers in the nineties.

Perhaps “weakest” or “least-best” are better terms, as this is not mean to be synonymous with bad (like the Beauty and the Beast Sing-Along, which might score a hypothetical -83% in satisfaction). Something has to come in last place, and that thing could still be excellent!

Enter Disney’s Old Key West Resort. Putting this property in last place is especially controversial with WDW diehards because it has a rich history and a lot of fans with very vested interests (in the most literal sense) in Old Key West.

Old Key West was originally named Disney’s Vacation Club Resort when it opened back in 1991. As in, it was the only one and seemingly intended to stay that way given the name. That quickly changed, and it was renamed to Old Key West in 1996 as DVC embarked on a period of explosive growth, which still has not really ended.

Being the proof of concept for concept for Disney’s timeshare model, Old Key West still has a different vibe than most other resorts. Longtime DVC Members, many of whom fell in love with Walt Disney World and have owned at OKW for three decades, are quite protective of it. There’s a reflexive reaction to any changes made to their sprawling home resort or criticism levied at it.

After a recent stay at OKW, we wanted to return to its ranking as our last place Deluxe or Deluxe Villa Resort, covering the good and bad, and why almost everything about Old Key West is a double-edged sword. Let’s go category by category…

Old Key West Theme

Old Key West captures the feeling of a bygone-era community in the Florida Keys that Disney has dubbed “Conch Flats,” with a mix of Victorian and Gingerbread architecture. The lush grounds and other thematic details go the extra mile in reinforcing the sense of community.

The way it is romanticized sufficiently distinguishes it from the (nearby-ish) real thing as well as condos and retirement villages around the Sunshine State. This is one potential point of criticism, that Old Key West isn’t quite as immersive or distinct from countless other areas in Florida.

I disagree. This one is not a double-edged sword for me. I love the themed design of Old Key West, and find that the overall ambiance has a relaxed, Jimmy Buffett-esque vibe that works really well for vacationing. If anything, Old Key West is underrated on the thematic front.

My one light bit of criticism here would be that recent modernization efforts to the Hospitality House have gone a bit too far. I miss the old Papa’s Den, charm of the main lobby, and intimacy of Olivia’s. I understand all felt a tad tired and look nicer now, but they could use a touch more personality.

Conch Flats is still great, from the Hospitality House itself to the Sandcastle Pool to the nearby lighthouse. The colorful outer buildings are likewise great, and all of this should serve as the aesthetic blueprint for the upcoming room redesign. Speaking of which…

Old Key West Guest Rooms

Old Key West completed a room refurbishment back in 2019, which was prior to the “cut off” for good redesigns at Walt Disney World. The end result of that was toning down the grandma’s cottage look significantly, but without the same functional improvements and more scattershot themed design.

Ironically, the new rooms are exactly like your grandma’s cottage in Florida would look if she bought sometime in the last decade. The old rooms had a Golden Girls look to them that was quite nice, and is coming back into style. They had personality and pizzazz, and matched the vibe of the resort.

The current rooms feel tired and lifeless. Fans often accuse the lodges of having dark and dreary rooms, but honestly, I think OKW (at least the studios) is worse in that regard. They’re not necessarily dark, but they are drab. These are the negatives of the current rooms.

The undeniable, objective positive is that the rooms at Old Key West are incredibly spacious. Even if they don’t perfectly maximize their floor plans, there’s a lot of breathing room.

Our most recent stay here was part of a split stay with a more modern studio after, and the contrast was stark. The other room had functional improvements and space-saving features, but still felt noticeably smaller…because it was!

The future potential positive is that Disney Vacation Club will be refurbishing the guest rooms at Old Key West sometime soon. That project was supposed to start this year, but it appears to have been pushed back until after the holiday season.

Just based on availability (or lack thereof), we’re anticipating a Spring 2027 start. We keep expecting something to be added to the calendar any day now, with more almost certain to be revealed at the upcoming condo association meeting in December at the absolute latest.

Disney Vacation Club is treating the upcoming soft goods refurbishment of Old Key West as a ‘semi-hard goods’ refurbishment. It’s unclear what, exactly, this means, but several other resorts received the pull-down sleeper sofas during similar projects.

The wildcard with OKW is the shape of the rooms, which may not be conducive to the pull-down sleepers. Either way, it’ll be a longer and more involved project, likely lasting throughout 2027 and potentially into 2028.

If Disney can find a way to add the pull-down sleeper sofas in the studios, that would be huge. That’s really all we ask. The larger rooms are even less conducive to adding the pull-downs, but also don’t need them nearly as much.

Even other improvements to the style and substance could make these among the very best rooms. DVC has been on a roll lately, and we’re cautiously optimistic that’ll continue with OKW.

Old Key West Restaurants

For a resort of its size, Old Key West has a lackluster dining scene. Good’s Food to Go might be the weakest main counter service restaurants at any Walt Disney World resort. Gurgling Suitcase is arguably underrated as a bar, but even so, most resorts have better options.

This pushes people to Olivia’s, which has a loyal fan-following. It’s basically the DVC family kitchen, and has several crave-worthy dishes. The fried chicken is amazing, and several breakfast options are likewise delicious. Even so, a single table service restaurant is insufficient for a resort of this size, and the overall slate is worse than even Saratoga Springs Resort.

However, many DVC members might shrug their shoulders at this. It is, after all, the Disney Vacation Club resort. The villas all have full kitchens or kitchenettes, and I wouldn’t be the least bit surprised if the average guest at OKW is more inclined to cook meals than the norm even at other DVC resorts.

Not only that, but Disney Springs is a short boat ride away and simply enjoying the Sassagoula River Cruise unlocks a wealth of world-class restaurants. Maybe the practical reality is that, between kitchens and Disney Springs, OKW does not need more dining capacity. That plus Olivia’s is enough.

I’m skeptical of this. Olivia’s is often busier than it should be for this tier of restaurant, as are the bar and walk-up window. Given the guest complaints we hear about dining around the Crescent Lake Resorts (and how excited fans are at the prospect of a proper counter service at BoardWalk), it’s hard to believe that OKW owners and guests are okay with this.

I’d go as far as to say OKW is Walt Disney World’s worst food resort at the Moderate or Deluxe tiers, and that includes several other resorts that also have kitchens or easy access to Disney Springs. Even both Port Orleans properties and Saratoga Springs are better.

OKW Transportation

Old Key West is the quintessential 1990s Walt Disney World resort, with a sprawling layout and multiple bus stops for transportation. Whether you view this as more or less convenient is a matter of personal preference.

For the average hotel guest, this has fallen out of favor. Walt Disney World is building more consolidated resorts for a reason, and that’s due to complaints about layout, size, and bus stops. This is why people prefer French Quarter of the two Port Orleans Resorts, and why Gran Destino and Riviera Resort exist.

With that said, the flip side of this is that the cluster building style is a gamechanger for guests with their own cars. I would once again hazard a guess that this is disproportionately common among OKW owners.

These outlying buildings enable guests to park right outside their villas, much closer than at most other resorts. (Personal vehicles could also help explain the dining situation, with guests driving elsewhere or even being more inclined to venture off-site.)

For our recent stay, I also put in a room request for the first time ever at Old Key West via the new online check-in feature. It was a relatively last-minute booking and there was no availability in the ‘Near Hospitality House,’ but we still managed to get Building 27 in the Peninsular Road Area.

This was perfect, and made for an incredibly easy walk over to the Hospitality House. Given that the most important amenities are all right there, this made OKW feel more consolidated and completely undercut past complaints about layout.

OKW Cost

This one depends on your perspective. Old Key West typically has the lowest Deluxe/Villa room rates, especially after discount. However, we would not put OKW on par with other Deluxes when paying out of pocket.

The resort is best suited for DVC owners with specific preferences who are paying with points. Most infrequent Walt Disney World guests would be better served by upgrading to something like one of the lodges (Kidani Village is often almost identically priced) or downgrading to the Moderates for less.

The flip side is that Old Key West is a great value when using points. Not only is the DVC point chart very favorable, but it’s one of the easiest resorts to book. Almost all of our stays at OKW (including this one!) have come when scrambling to find last-minute DVC availability, and left with only this or Saratoga Springs as the choices.

Of course, Old Key West having the best availability when booking via points also speaks to its lower popularity even among Disney Vacation Club members. In so doing, it undercuts some of the above that owners are okay with the compromises at OKW.

Its owners will dispute this, much like Animal Kingdom fans argue it’s a full day park even without Tropical Americas. But people ultimately vote with their feet and wallets, and availability tells the story pretty conclusively when it comes to Old Key West (or Animal Kingdom with its afternoon exodus).

Old Key West Conclusion

Ultimately, there’s plenty to like about Old Key West and there are certain demographics of Walt Disney World fans for whom the property is tailor-made. That’s true of every single resort, and why it’s plausible for any to rank as a personal #1 without drawing the sid-eye of skepticism that fans of the Beauty and the Beast Sing-Along would receive.

The rooms are spacious, Olivia’s has a cult-following for a reason and the rest of the restaurant scene can be passable if you supplement with cooking in your kitchen, dining at Disney Springs, or driving off-site. And speaking of which, having your own personal vehicle or rental car is a complete game-changer for opinions on Old Key West, likely catapulting it above many other resorts to at least middle of the pack.

Old Key West is a resort that I really want to love. The theme and atmosphere are incredibly underrated, and it’s an exemplar of 1990s early-Eisner era design in the best way possible. I might even go as far as to say Old Key West actually offers the kind of vibes that Poly purports to (or once did). It’s difficult to articulate, but OKW also has a certain x-factor (perhaps the “Buffett-Factor”) that just makes it so much more pleasant of a place.

I’m also optimistic about Old Key West’s future. There’s nowhere to go but up with the coming semi-hard goods room refurbishment, and that alone has the potential to move it up a few spots on our personal list. On top of that, Walt Disney World has been making a concerted effort to improve dining at other resorts, and the same happening at OKW would certainly help our opinion of it.

But for now, from a practical perspective and the places we want to actually stay or recommend to casual guests and infrequent visitors, there’s a reason why OKW is towards the bottom of our Rankings of ALL Walt Disney World Hotels from Worst to Best. Here’s hoping that changes and Disney’s Old Key West Resort moves up in 2027 or 2028!

If you’re thinking about joining DVC, be sure to read our Ultimate Guide to Disney Vacation Club. This covers the pros & cons, resale v. direct, how much money you’ll save, and other important things to know before taking the plunge. If you still can’t decide whether membership is right for you, “try before you buy” with the recommendations in How to Save BIG on Deluxe Disney Accommodations Renting DVC Points.

Your Thoughts

What do you think of Disney’s Old Key West Resort? Do you stay here or avoid it for any of the reasons above? Thoughts on the room size or quality, dining, transportation/layout or anything else about OKW? Is there another variable that makes it the best or worst pick for you? Do you agree or disagree with our assessment? Any questions we can help you answer? Hearing your feedback–even when you disagree with us–is both interesting to us and helpful to other readers, so please share your thoughts below in the comments!