ok, so I like to travel for vacations a good bit. I mostly use frequent flyer miles, and I realize this might not be an option for you. I don't know what your budget is so here are some of my thoughts.
I like bookit.com, orbitz.com, travelocity.com if you don't want to take a lot of time looking at hotels and book whatever at a decent price and not be a dump. (you won't be great either)
if you are willing to take the time and look through a lot of rentals
vrbo.com
This stands for vacation rental by owner. This gives owners the chance to list their places for rent. You can find much nicer places for a cheaper price IMO.
Vacations, Resorts, and All-Inclusive Packages | CheapCaribbean.com is another good one. If you have southwest Frequent flyer miles you can find some real steals on this website. The reason you need southwest is because all prices that include airlines are flying out of Miami. If you have SW you can fly there for free and get a dirt cheap ticket to fly out of there. This is also where I like to look for cruises
Some things to consider. If you decide to take a cruise the closer you wait until the departure date the cheaper your cruise tickets become, but the more expensive your plane tickets become. This is a hard balancing act because if you buy the plan tickets early there is potential that your cruise could sell out.
I do not like carnival cruises. One big reason is the dinner seating. I do not like being told what time I have to eat dinner and having to sit with random people to hear their life story.
I did enjoy Norwegian
Places to visit
Favorites: Cancun, Hawaii
Good for a closer trip: Destin Florida, Bahamas
Least Favorite: Pretty much not much of a fan of east coast beaches. (that is just personal preference)
Mentioned before was sandals. I have never used them so I have no opinion of this.
hope this helps