I just got back from Miami with my boys to celebrate my birthday weekend (or our first family vacation together). We decided to test Ronak out with a sunny location that had no time difference so his schedule wouldn't be too impacted, and the flight needed to be as short as possible. Of course Florida was the ideal location with a 3 hour direct flight. We ended up booking our whole trip (flight and hotel) through expedia.ca, which cost us 1400 for the 3 of us for 4 nights. The fact that kids are free until 2 is so fantastic!! We booked the Loew's hotel right on Collins Avenue, because of the great reviews on how baby friendly it was. If your a parent and staying in South Beach I would strongly recommend this hotel. They provided us with a stroller (long story on how we forgot our actual stroller at home), a car seat, baby tub, and random baby toys. You can find great deals for this hotel depending on when you book. September was a great time to go, the whether was still warm (while in Toronto it was starting to feel like fall), and it wasn't full of the young 18 year old summer crowd.
Both my husband and I have been to Miami before so we spent most of our days by the pool and the beach. We tried some great cuban food at "Young Urban Cuban American" on Lincoln Road (which also has some great shopping too), had an amazing dinner at Mr. Chow (Ronak fell asleep) in the W hotel, and did quite a bit of outlet shopping at Sawgrass Mills which I would highly recommend.
See some pics below: