Some people ask me to help booking their trips. They ask me because usually I found cheaper flights and hotels. So the question is not if exists any flight or hotel booking site as Kayak, Trivago or the service offered by travel agencies. The question is if there is any service that given a vague description of the travel you want, find the best options.
For example, if you ask for a trip "between March 2nd and 10th to a caribbean beach", they offer a touristic package to Cuba from 3rd to 10th, a flight to maldives islands in a 4* hotel, etc. The idea is that you just describe the trip you want and they give you some budget options.
I'd like to know if there is such page to redirect all my friends who ask me to do their holiday finding job :)
EDIT: 3 years after I ask about this, I'm still looking for travels for my friends. I've found sites like Flighfox but this is flight-centric, I'm looking for something similar to the experience of getting to a physical travel agency and ask for a holiday package (or a flight or a cruise or a hotel...) I can't believe it doesn't still exist. May be there are no a unique website, may be exists Flighfox for flying, XXX for travel packages, Trivago for hotels, ... (well, really Trivago don't accept natural language, you must specify dates, place, etc, my friends come and ask about "I'd like to go to south France coast one week in July, could you find me something cheap, please?")
Just to clarify, copy&paste (and edit) a comment I made when I asked this 3 years ago: "My friends and other people I talk with don't know/like to use websites like Kayak, EasyJet Holidays or similar. For them (comming from an analogic world) travels are arranged by asking someone what they want: "I want to go to Paris next week" and don't understand that computers need to specify exactly or approximately where and when you want to go. The point is "informality", not natural language processing.
NOTE: No tips about how to deal with tiring friends ;)