1. http://www.travelzoo.com/ : This site provides you with weekly emails with links to other sites offering great travel steals as well as great discount tickets for events near you. You get the email each Wednesday and its always worth taking a look at the weekly bargins. Some of the deals offered will really blow your mind. Ex: Up-scale hotels in Miami and Chicago for $80 a night, airlines having huge flight sales, etc.
2. http://www.applevacations.com/ : Helps you book your entire vacay! Most resorts are all-inclusive and you can find some super steals in the 'specials' section. This section provides deals for up to 2/3 months out. Put in your departure city and it shows you whats available. Example: 7-nights all-inclusive to Punta Cana from Cincinnati for $899 a person. One of my favorite old co-workers scored one of these deals in September. He and his wife went to Punta Cana and he said the resort was top notch! $899 for EVERYTHING for one week is such an insane deal; especially a week in the Caribbean :)
3. http://www.vrbo.com/ : We used this site this summer when booking our family vacay to NC. It's a site where everyday people, who own property, place their homes/condos to be rented out. It's great because it provies you with direct contact with the homeowner as well as reviews from others who have stayed at the property. Many times, you can even negoiate a better price for a vacation rental; especially when waiting last minute :) These people want their properties booked and will often work with you on price to make that happen! Furthermore, you arent just limited to looking at places in the US! Check out the deals for St. Lucia and other hot spots in the Caribbean. AMAZING deals for goregous properties!!!
4. http://www.allinclusiveoutlet.com/ : I used this site a few years ago when going to Jamaica for my best friend's wedding. It, like Apple, plans your entire vacay from flight to resort. They are just a great company, that happens to be based right here in Lex! They set me up at a top-notch resort for an excellent price :)
5. http://www.cheapcaribbean.com/ : I have never booked anything through this site, but I receive their weekly emails. They are always offering some pretty awesome deals to all of those warm, fantastic, destinations many of us wish we were currently enjoying.
Of course, I always recommend my go-to sites http://www.hotwire.com/ and http://www.priceline.com/ for great hotel and car rental deals! I know some of you (who shall remain nameless ;) are still "nervous" about what you will get, but I promise, I've never been let down!! We scored a great little room right outside of Disney's gates for $57 a night (including tax) over New Year. Crazy, right?! I tried to add a picture, but miss un-tech savvy here cant figure it out. Just check out my fb album to see the room :)