Several years ago we wanted to get together with all the kids and go to Disney World. It was a little pricey to house everyone at the World so we latched on to the idea of renting a house that would fit all of us. At that time it was only 9 adults and four kids. On the internet, I found a site called VRBO, Vacation Rentals By Owners. (There is another site, Dwellable, but we haven't had occasion to use them yet). And on the site, found what we dubbed, The Mickey House.
The house had a pool, rooms for each family, and a large kitchen. We were able to save money by eating breakfast at the house, packing lunches, and eating dinner often there. The house was not so far from the park that we couldn't drive back for evening festivities. Needless to say the kids enjoyed the pool and hot tub almost as much as the World.
Our second venture to Disney a few years later, we rented a house a little closer to the park. Now there were nine adults and six kids. The house was not quite as nice as the first had been but still fit our needs and its location to the park made it even easier to get back and forth during the day giving the kids some nap time or at least quiet time.
We have used VRBO often for other ventures including a couple of trips to Florida and Hawaii. (This year's condo has been absolutely perfect!) So far it has worked out well. But you have to do your homework.
1. Scrutinize all the amenities. Does it have washer and dryer, dishwasher, internet? Flat screen TV is always a plus for my husband especially if we are planning a long stay. Make a list of what you absolutely feel you need for your length of stay and look for those things. You might also want to see if the community/resort it's located in has a website to check out those amenities.
2. Check out the area where it's located. We use Google Maps a lot for this and once we locate the place, we go to satellite view and see what is around it. If possible go to street view and check it out as well.
3. Check references. Now this gets a bit tricky sometimes because it's hard to know if all the owners' friends are posting positive comments. For this I usually try to see if they are on TripAdvisor.com or just search online for the name of the house/condo and add the word review.
4. Correspond with the owner. Ask a question or two and see what the response is. You might ask about availability even though that is usually marked on a calendar on the site or ask about how near it is to the places you want to see. Ask about the amenities in the resort or community where it's located and if renters have access to them. You might ask about cleaning services if you have a lengthy stay and if you are required to use them during your stay. You will get a feeling of confidence or no confidence from the answers that come.
5. Be sure you understand the rental agreement. Usually there is a small deposit with the balance due a few weeks before you arrive. You should not have to pay everything up front to hold the rental.
Those are a few ideas to get you started. I can't guarantee that you will always be absolutely satisfied with your rental. It's like any other place you book for a stay. A lot depends upon your expectations. Remember to give a good reference when you have enjoyed your stay and temper a bad reference with where you set your expectations. Someone else may think it was paradise.