Who have you rented through that you liked? There are so many and I've never gone that route. A little nervous...
Sorry, the one I used last year isn't available anymore because I checked about getting it for next fall. But there were a number of other good condos I found while searching. If you need a place in Destin or Indian Rocks (tiny bit south of Clearwater), I can give you that information, but the condos at Vista Cay seem to change availability from year to year so much so I dont really have a specific one in mind I could tell you about.
I know some people have vrbo horror stories, but I've never had any problems. I booked houses and homestays all across Europe using vrbo without any problems, and that wasnt even in English! I've also used vrbo for different beach houses and various Orlando trips. We get so much more for our money staying in a house or a condo, and it is ten times nicer than any hotel. I always feel like Im vacationing from home. I hate staying in hotels if it can be avoided.
I think the trick is to do your research and to be careful.
1. I only book from people who have a number of good independent reviews not submitted by the homeowner.
2. Obviously, all the basics should be included. It should clearly state in writing what those are: internet, cable, air con/heat, appliances, washing machine, dishes, pots and pans, toiletries etc.
3. I specifically look for the places with the extras. These are usually listed in the fine print and by reviewers who comment on how nice it was that X was provided. Most really good deals will include some combination of the following: hot tubs / pools or access to them through a resort, a grill, board games, a game room, a game system, smart tv with movies, pool/beach toys/chairs/umbrellas/towels/coolers and wagon to pull it all in, books, movies, possibly a computer/printer or iPad, bikes, canoes or kayaks, a golf cart, local area information including restaurants, activities, and directions. Dont expect all that in one house, but look for the amenities that will be the biggest benefit for your family. There should be at least a few extras and definitely good local information provided.
For instance, there is one place I really want to rent from sometime that is Harry Potter themed, and they provide basic groceries for you like eggs, milk, and bread and at Christmas, they decorate the house and provide a X-mas tree. There is another place in Tampa I came across but we ruled out because of all the breakables, but it was lake-front with a private sandy beach and the use of jet skis. Another house I found in Orlando had a game room, pool, and mini put-put course. These are all examples of multi-room houses for less than $2000 a week. So, for about the same or less than what I would pay for two standard hotel rooms for the week, we can have an entire house with full kitchen to cook our own meals, plus private pool/spa, games, movies, and who knows what else to entertain us, multiple bathrooms (big deal for us as we have Crohns in the family), and everyone gets their own bedroom, so I dont have to sleep with kids! Worth it for that alone.
4. Through reviews, I try to determine how a certain seller handles issues. No rental will be perfect. I dont expect that, but how they handle fixing a previous renters issue, will tell me a lot about if they are someone I want to rent from. If someone reports an issue and a great response getting it taken care of, thats who I want to rent from.
5. I also prefer places being rented by individual owners who live nearby because I feel you get more individual attention and a better chance of them taking care of an issue if it is a personal matter to them. Plus I feel a person who is renting an actual home they live in will take better care of it than a person who never stays there and just hires a company to manage it. Although, I have done both.
6. I wont rent if the place doesnt have up to date pictures of all the rooms / yard. If you cant see that this is a real house and not stock photos, or if Im unsure about what half the house looks like, no way am I renting. I like to look for recent reviews that say the house is true to the pics. Also, if I see the same photos posted for another different listing, that throws up a red flag, and I won't rent it. I want a real persons house. It should be unique. If there is a double out there, then that tells me something is wrong.
7. When I think Ive found a suitable match, I then do a google search. Many times people have the place listed under more than one rental website, so this way I can look at other reviews and check to make sure it is not getting double booked anywhere. I will also look up the resort or neighborhood if I am unfamiliar with it to check for location, safety, and amenities.
8. It is also best if you book through a listing that offers the online payment option. This way if there is any issue, you can get your money back. Ive never just sent someone a check. I pay through the vrbo website. If I do write a check, it is only after arriving and inspecting the property.
Its not a quick simple process choosing a place. I usually spend a few days sifting through listings narrowing down my choices.
Renting from Vista Cay shouldnt be too overwhelming though. You are already narrowing down the rentals in all of greater Orlando to one small resort.
What I do is put in my dates and then use the map view potion of vrbo. You will notice that Vista Cay is divided into two different sections. The main section is the one by Walgreens. The extra section is the one by Publix. Some of the rentals in the Publix section dont have access to the main resort, so keep that in mind. It is a tradeoff. Some of those condos are cheaper because they dont have access to the main pool, movie theater, or club house. Though, they still have access to their own smaller pool and hot tub. We have stayed in the smaller Publix section before, and it was fine. We didnt have much time to spend at the resort anyway.
The next thing to factor in is do you want a fireworks view? Will you be there during any Sea World fireworks nights to take advantage of it? Only condos on the top floors, facing the lake, on the lake, have those views. We had one and never were around to use it.
Next question is will you use the club house and main pool area? Will you send kids or teens there alone? There are a few condos with balconies that face the pool / main club area, so that you can watch kids from your balcony if that is important to you, or if just being close to that area is important.
Once you have the general section you want to stay in narrowed down, you can start looking at the pictures, amenities, and reviews for those condos. There arent that many to sort through. But there are a few with good reviews and extra ammenities. From what Ive read, I would avoid the town houses and stick to the condos. Apparently, the town houses have a lot of stairs and confusing layouts. Ive never really heard complaints about the condos, only the town houses. The best places will book up well in advance, so start looking as early as possible. You can usually tell the preferred places becuase they have like 40 reviews compared to 2, and book up a year in advance.
Good luck!