How do these experiences compare to OKW?
I have never stayed at any of these three options, but I would imagine they are more similar than they are different…
Whereas, I would imagine AKV is more different than similar to OKW, WH, and BC.
OKW is the only DISNEY property, besides AKL. That makes a big difference in transportation, some costs, and feel compared to the others.
And I totally respectfully disagree w a pp who said OKW looks like 80s condos.

It’s a gorgeous, whimsical, colorful, wooden, relaxed property right on a golf course, not at all like a typical crappy cement condo. If it was, I would never have stayed there because that’s the last thing I’d want when on my hard-earned vacation time at Disney. I will say we avoided it for years, drove through too see it but weren’t overly impressed. Until we stayed in two Studios and fell in love with it. This past Sept my family had two 1BR units. Hopefully one of these days we can score a 3BR unit. As I said before, my son, who’s your age and stayed at all the Disney properties listed in my signature, mentioned several times he really loved it there and it was now (just clarified w him) his
second favorite of the Disney resorts. We all felt the same way and can’t wait for our next stay. A good friend of mine just checked into OKW today they’ve owned there since the 90s. They don’t even stay anywhere else, by choice.
Wyndham is right on the border of Disney property but not on Disney property and not owned by Disney. I have heard good reports of it, have directed people there, and took a tour once to see it in case we ever decided to stay there. It has a lazy river which is nice. A Disney friend stayed in the presidential suite and said it was awesome.
Windsor HIlls, have never been there, so can’t speak for it. When my son was playing college baseball and we stayed in the area for tournaments we got to see some of the various off site properties where the teams stayed and looked into booking them ourselves, to be closer to him (for the few times he could come out with us). We almost always wound up back at Disney except the time I had to take my elderly mother with us as well as DS’s girlfriend and we needed a bigger condo near where the team was. The condo was nice but, while it did have some unique features, it wasn’t at all Disney, the kids’ pool was nice but the adult pool horrible, the area was sketchy and not where we wanted to be, and we sometimes got lost trying to get around.
There was an incident in the news recently about Windsor HIlls you probably want to consider.
https://www.positivelyosceola.com/5...nt-exposure-incidents-at-kissimmee-resort-fl/
Honestly, I think you were on the right track originally, deciding between AKL and OKW. If your fiance has the money and doesn’t mind spending an extra $3K to experience the animals and beauty of AKL, then go for it. But if you decide to go the OKW route, don’t worry about really enjoying it. It sounds like you aren’t even going to be around the resort much, anyway, but it is a nice chill place to hang out when you are. Maybe a nice trip for the two of you some time to AKL is in order later when you can spend more time there. I’m like you and like to save money where I can.
Sharing some pictures of OKW
Hard to see, but note golfers on the course
Reception
Olivia’s famous Buttermilk Chicken (which was very good) and Sangria
I’d add more pictures but ten is the limit. Maybe look at more online.
The other thing I want to say (I left a Recreation link in my earlier post) is that there is a ton to do around the resort that your particular group may enjoy - basketball, tennis, pickleball, volleyball, hammocks, pool table, surrey bikes and lots more. Will add the link again. It’s also not crawling with people, which we’ve found, especially lately, some of the other resorts are (though it likely depends when you go). Good luck with your decision.
https://disneyworld.disney.go.com/resorts/old-key-west-resort/recreation/