Wow, we can't remember a better time to book a family getaway in the Caribbean, with killer deals and special promotions dropping out of the sky every day. Still, we've learned the hard way that deals aren't always as good as they seem at first glance. So we got out our calculators and did the math on four seemingly terrific deals. Here's a peek at how we separated the sunny steals from the washouts.

Bailout Package at Aruba's Westin

Everybody's looking for a bailout these days -- but as we've all seen, not all bailouts are worth having. Take the Vacation Bailout package at Aruba's Westin resort: If you book a six-night stay, you get a $200 resort credit and one night free. Sounds great, right?

The 481-room resort has a beautiful beach and awesome freeform swimming pool, and offers plenty of places to spend that resort credit, such as the spa, casino, and solid (but, alas, not free) kids' program for ages 6 to 12. Its Destination Club features crafts, sandcastle-building, iguana-feeding, a Little Chefs cooking class, and Friday evening s'more roasts.

When we priced a trip with the bailout package rate (factoring in the resort credit), a room with two queen beds came to about $2,300 for six nights -- a $700 savings compared to normal rates. The Vacation Bailout must be booked by December 31, but you can travel through April 16, 2009.

Deal or no deal? It's a deal, but not as good as you'd think. Book the resort's "Better Tomorrows" package instead, which gives you 50% off for every other night you stay (thus averaging a 25% savings over two nights). It brings the same six-night total to $2,050 -- not only $250 cheaper than the bailout package, but all the savings go back to you. Now that's what we call a bailout. To take advantage of the Better Tomorrows package, you must arrive Thursday through Sunday, and travel by March 31, 2009. 

Save 50% at All-Inclusive Almond Resorts

Wow! Half-price Caribbean deals keep landing at our feet. This one is offered by Almond Resorts, which has five all-inclusive properties on Barbados and St. Lucia. Four of the properties welcome families, while one is adults-only. Rates include unlimited food and beverage (á la carte, buffet-style, and room-service) and most activities, including kids' programming for kids, from newborns to teens.

Of the four family-friendly properties, the two least expensive options are those on St. Lucia, the Almond Smugglers Cove Resort and Almond Morgan Bay Resort. With this deal, an all-inclusive four-day/three-night stay for a family of four can be had for as little as $900 if booking land only. Packages including airfare are also available; we price-checked the same four-day stay for a family of four at $3,450 if flying out of New York in January.

Note: American Airlines has increased non-stop service from New York's JFK to St. Lucia three times a week. In addition, American Airlines flies direct from Miami daily, while American Eagle serves St. Lucia from Puerto Rico five times a day.

This offer is available for bookings through December 19. You must travel by February 9, 2009.

Get 50% Off at Wyndham Nassau in The Bahamas

Some deals are more spin than substance, so when we see one that's a guaranteed money-saver we sit up and take notice. The Wyndham Nassau Resort & Crystal Palace Casino is offering a Vacation Stimulus package: stay two consecutive nights between now and the end of 2009 and get the next two nights free. That translates into a hefty 50% discount. The package also includes a $100 food and beverage credit for use at the resort. Rates begin at $309 per night for an oceanview room, so a four-night stay would cost from $618 -- averaging just $155 a night (plus dining credit). The booking deadline is January 31, 2009. The fine print says the number of available with this deal are limited, so don't wait too long if you want specific travel dates.

Winter Sale on St. Maarten

Faced with a sickly global economy and airline route cutbacks, the tourist offices of Caribbean islands have been stepping up promotions to entice travelers to their tropical shores. Case in point: The island of St. Maarten is running a "2009 Winter Sale" that offers a 15% discount on regular rates at nine resorts on the island. You need to book by January 31, 2009, and travel between December 20 and April 30, 2009. Stay seven nights or longer, and you'll also get $100 in "spending credits" good at nearly 50 island restaurants, spas, nightspots, and spas.

Times have been tough for tourism in St. Maarten, and deals are plentiful. So we decided to see if the winter sale was really the best deal on the table right now. Here's what we found:

  • Three of the hotels participating in the winter sale -- La Vista Hotel, Mary's Boon Hotel, and Oyster Bay -- are not running any additional deals, so the 15% discount is the best option.
  • Two hotels that are participating in the winter sale -- Coral Beach Club and Turquoise Shell Inn -- are offering other promotions that offer the equivalent of 15% savings. Note: We question the kid-friendliness of Turquoise Shell Inn, as it doesn't accept children under 5.

Here's where things get more interesting:

  • At the Princess Heights Hotel, a "book early" special gives a 20% discount for stays booked by December 14 (less than two weeks away, so hurry). The deal also includes a free rental car.
  • Sister resorts Sonesta Great Bay and Sonesta Maho Beach are both offering discounts of up to 35% for stays between December 20 and January 31, 2009. Savings are on a sliding scale depending on number of nights stayed; you save 25% when you stay two to four nights, and more when you visit for five to nine nights.
  • Divi Little Bay Beach Resort is advertising two specials on its site. The "beat the clock" deal lets you save 30% if you stay before December 20. You can also save 30% by reserving before December 20 and traveling between March 15 and December 23, 2009.

Deal or no deal? While a 15% discount seems pretty good at face value, it's anemic when you look at the big picture at some of the partipating resorts. In fact, you can do twice as well by booking other online deals at four of the participating hotels. You can save 30% at Divi Little Bay Beach Resort and up to 35% if you book at least five nights at Sonesta Great Bay or Sonesta Maho Beach.

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