Didn't see anyone else post, so thought I'd comment. Hopefully you will hear from others who have used this site more recently than I have too. I've only used Redweek.com three times, but it did work out great for us all three times. It was very easy to setup a stay with the owner, and the three different parties we dealt with were all great to work with. // I booked my stays about the same time that I booked my airline tickets, about four months in advance. I was happy with the price and didn't keep checking etc., so don't know about deals closer to the time. I've been coming down to Orlando for years, over 20 trips, so am pretty familiar with what seems like a good price for a condo. I have usually found more reasonable prices at timeshares that are larger with lots of renters (Cypress Point -- owners seem to have flexible week and can get your dates) // Sheraton Vistana Resort -- fixed weeks, but a huge resort - so usually plenty of owners renting units your week and all sections are nice).
The cancellation policies of the individual owners I was dealing with weren't good for last minute cancellations. If you need something that is fully cancelable due to uncertainty, this might not be a good option for you. Or you may need to take out your own insurance. An individual owner might just have one or a few timeshare weeks. They are going to be less flexible than a company with tons of units and tons of business. They want to make sure they get the rents to cover their maintenance fee, etc. I have found small privately owned lodges, etc. to be similar to this too.
Orlando is overbuilt so there are lots of different sources and ways to go. TUG2.net classified ads section has a bargain basement section for last minute deals that you might want to take a look at if you are most interested in a last minute booking and getting the best deal you can. This (TUG2.net) is a timeshare users group website that I have done lots of rentals from. They have a regular classified ads section and a last minute one too.
And maybe as a backup just in the off chance you don't find a last minute deal you like, you could book something fully cancelable you could live with and then cancel it if you find a great last minute bargain??
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One comment on last minute for flexible in price. For a Marriott timeshare resort in West Palm Beach, I remember years back renting one unit for $1200 for a week (unit slept eight) and wanting a second (large extended family group). Retail at the time was $380 a night plus tax on the same units from Marriott. I booked my original unit 10 months in advance from an owner on TUG (looked into the want to trade area and found someone willing to rent for me for $1200 -- they were going to trade with Marriott for airline tickets, but was willing to rent to me for the cash they needed for the tickets), kept looking every month or so, but only saw one of the person advertising a unit and they wanted $3000 for the week, which I thought was way too high. Anyway, I contacted them anyway, knew they had been advertising for at least three months, mentioned that I had rented a unit for $1200 and asked if they would rent theirs for that. They told me no way, that they could easily get $3000. Anyway, I was really nice and said that if they changed their mind even very last minute, to give me a call. In the meantime, to make sure I'd have something where folks could stay I booked a fully cancelable reservation at a more basic hotel across the street for $180 a night (a double queen room I hoped I wouldn't need to use). It wasn't looking good. But three weeks before my trip, the folks called me and rented me their unit for $1200 which I was thrilled about. // This is a totally different market than Orlando though. In Orlando there is so much to rent -- renter's market.
