Airfare Watchdog is an awesome website for airfare prices. This site tracks airfare and really helps you save. You can sign up for the newsletter, which will alert you when there are low fares.
I also check out Kayak.com a lot to compare airfares.
If you're looking for a hot deal on somewhere to stay in the Caribbean, be sure to check out Cheap Caribbean. If you're up for a spontaneous trip, you may want to check out their last minute deals. They are also offering a promotion where kids get to stay and eat FREE at various resorts! Go HERE to check out the deals.
Overall, I have personally found that they offer the best prices on All-Inclusive trips.
If you like surprises, you can book a hotel through Priceline or Hotwire. While you will not know exactly which hotel you are staying at (until after you book it), you can choose which area you want to stay in and the best part is that you get to choose the price!
You can also choose how upscale (or low-scale!) you want! My sister-in-law uses this all the time, and she loves it!
Did you know that Craigslist has a section that is devoted to Vacation Rentals? Look up the area you want to stay in and then search under the heading "Housing". While I have not personally stayed at a place from Craigslist, I have browsed it many times.
This could be a good option for a vacation on the cheap.
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