If you can afford it (and you're looking for a place with the/a lady), I'm not sure you'll beat :Jade Mountain in St. Lucia":http://www.jademountain.com/default.html .

Each "3-wall" room has an infinity pool IN the room, in addition to all the other high-level luxuries and touches afforded in the Caribbean.

Just be aware that most married guys I know that go there return with pregnant wives...

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For the kid in you, nothing beats a Disney World vacation. For under $5000 you can stay at one of their premium resorts, with a week long pass to every park, and a dining plan for each person.

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I always use aavacations.com to plan my vacations. Usually you can find good deals on all-inclusive resorts with flight included.
I love doing all-inclusive because everything is taken care of and I don't have to carry around money. I just lounge around at the beach or pool all day and, on the last day, throw a $20 to anybody who has been helpful (bartenders, etc...). I've had really good luck with places in Riviera Maya.

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