I’m a big fan of renting other people’s timeshares – often for about the cost of the annual maintenance on their time share. There’s a resort in cabo I’ve been to a few times that I like to rent at.

Like ER – I use homeshares, VRBO, but also look at timeshares – since I prefer a place with a kitchen and separate bedroom (when travelling with kids.)

Timeshares commit you to the same place and/or the same family of timeshares for the same week, every year. Might work if you have a fixed vacation – but it’s too inflexible for me.