Have you ever booked a room or flight on a discount or budget site, thinking you were getting a great deal, only to regret your purchase? Several years ago, we booked a flight on a budget airline to Las Vegas, thinking we were getting a great deal. Almost too good. After it was booked, we discovered that the couple hundred dollars we saved, we were actually going to pay for in hidden fees that would have come included in our other option.
It was a monetary wash but you get what you pay for, right? Not only did we have hidden fees tacked onto our airfare, we lost hours, upon hours, of time spent in the airport terminal waiting for plane equipment issues to resolve on our return trip. It took so long to get the equipment issues fixed, that when they were finally done, the flight crew was unable to fly the plane due to the number of hours they were already on the clock. Another crew was called in, but never made it. We were almost given hotel vouchers, to stay the night, but we ended up being rebooked onto another airline for our trip home.
"Do you about any good deals?" That's a common question posed to travel agents and can be a frustrating one. It's a very generic travel request, narrowing down the destination search to.... Earth. A 'great deal' to one person may mean something different to the next. Are you looking for the rock bottom price for the cheapest hotel, or a extra perks for a luxury villa? Most often it's cheap rates, as most of us want to get something GREAT, but don't want to feel we could have found something similar at a better price.
If you're looking at a vacation, either through a travel agent or self-booking with an online booking engine, there are some things to consider when considering your options on those cheap 'deals.'
Getting to Your Destination
"Something tropical" is a popular destination request. Whether you're looking at Mexico, Caribbean, Maldives, or Thailand, you're sure to encounter a variety of price points in each. The first consideration is the cost of airfare to the destination and whether it will be included in your vacation package. If the airfare is packaged, check to see which airline would be offered and what fare type is included with the package. Will it be basic economy or business class? 
You may save money for the initial airfare by booking the cheapest rate but beware of the not so hidden fees. Added expenses for luggage, seat selection, early check in, or in-flight beverages/snacks may end up making that cheap fare more expensive than other options in the end.
Time of Year
Just about any location you travel to will have a peak and low season and the cheaper the rates, generally indicates a time that is not frequently traveled. It's important to understand why the rates are lower for that destination during that time. Is it hurricane season in the Caribbean? Will your trip to Europe be cold and rainy? Are you flexible enough to enjoy your time during less than favorable weather conditions?
While you may not want to deal with the crowds during peak season, booking during the "shoulder" seasons, on either side of the peak months, may provide you with that sweet spot of fewer crowds but favorable conditions.
The Brand
As with anything, the brand you're booking can greatly impact your vacation experience. A "deal" with a mass market cruise line will come with different value than a "deal" with a premium or luxury cruise line. The level of customer service, cuisine, and amenities offered can vary greatly. If you see a special on a vacation package, be sure to at least find out what level of brand you are purchasing into.
Age of Ship/Resort
When booking a cruise or a resort vacation, you may find what appears to be similar amenities but different pricing. It's possible that the age of the cruise ship or resort is a factor. Cruise lines know demand for the shiny, newer cruise ships will withstand a larger fare. Similarly, a resort that is considered a "cheap" deal may be nearing it's renovation time and appear "tired" or in need of a remodel.
You can certainly still have an enjoyable time, but may be missing out on newer technology and amenities that the newer ships or resorts offer.
Location within Ship or Resort
Along with the age of the ship or resort, you may also consider the location of your room. Will your cruise stateroom be under the pool deck or nightclub? Will your resort room be facing the road or into the side of another resort? There are vacations where you may not spend a lot of time in your room, but for those times you want to relax or get some good sleep, you want a comfortable environment. They may be the least expensive but is it worth it to you for the inconvenience of excessive noise or without a better view?
Inclusions
As mentioned above about airfare, the cheaper rates often come with fewer inclusions or amenities. A better deal for you may include transfers between the hotel and airport, a drink card or excursions on your cruise, or maybe a VIP butler treatment at your resort. The inclusions are not always the same across different suppliers, so it's important to compare what they each have to offer. Some are in the form of resort coupons or on board cruise credit, others will be upgraded rooms. 
So How Do You Choose?
Ultimately, it's up to the individual traveler on which vacation package is a better value. If you're planning your vacation on your own, be sure to research each of the suppliers to the destination you've decided on, so you can compare similar resorts or cruises for each... apples to apples. Also, try to find updated reviews to make sure the info the suppliers are providing is consistent with what recent travelers have experienced. Check the typical weather patterns and temperature ranges for the destination during the time you are considering to travel.
If you don't have the time to deal with all of the researching and comparisons, we'd be happy to help you plan your vacation. We have a network of colleagues and contacts with travel suppliers to help make sure information about your cruise or resort is as up-to-date as possible. Not only do we help with the booking, we call your resort to confirm reservations prior to arrival, watch for any situations that may affect your vacation, prepare travel documents for you, and are just a phone call away if you have any questions before, during, or after your vacation. The best part is that, in most cases, we do this for no additional cost for you.
In the end, your vacation should be as relaxing and enjoyable as possible. Whether self booking or using a travel agent, keep in mind the cheapest rates may not be the best experience you can afford. Be sure that your "deal" is the best for the vacation you want to experience.