Jamaica Vacations From $395, Plus Aruba, Costa Rica, More*

Though her identity remains shrouded in mystery, we do know this much about the Deal Detective: She's a no-nonsense sleuth with a lifetime's worth of experience investigating travel bargains.

See recent posts by The Deal Detective

The Deal Detective is SmarterTravel.com’s resident bargain hunter, Kate Hamman. She’s always on the lookout for new travel deals and invites you, dear reader, to submit your own questions.

Tracy in Texas writes, “I am looking to have a vacation with my teenage daughter in Jamaica. We have had terrible luck with our last three vacations, getting caught in a monsoon in Mexico one year and could not leave the hotel, the next year could not swim in ocean in Florida due to shark attacks and the last vacation was white water rafting where we lost all of our luggage. I would love to show her that we can go on a disaster free vacation.”

Sounds like it’s high time you and your daughter had a relaxing trip, and Jamaica could be just the ticket.

With endless beaches, shopping, and water activities, Jamaica can be the ideal getaway destination. And these days, the deals are plentiful, too. For instance, CheapCarribean.com is promoting an up to 60 percent off sale on packages around the island, including a three-night stay at the all-inclusive Sunset Beach Resort and Spa in Montego Bay starting at $399 per person (without taxes and fees). The package also comes with round-trip airfare, weather insurance, and $100 off coupon if it rains during your vacation. The same deal typically costs about $799 per person. You must travel by August 31, and book by June 30.

Jetblue is also offering discounts on packages to Jamaica starting at $395 per person (without taxes and fees) for a three-night stay at the all-inclusive Holiday Inn Sunspree Resort in Montego Bay, as well as round-trip airfare from New York City (other departure cities are available at a higher price). Package prices change weekly, so book when you find the right price for your budget.

A resort can take a lot of the legwork out of planning, especially if it’s all inclusive. Many offer on-site restaurants, bars, nightly entertainment, and activities, making it easy to never even leave the grounds. This might be just the ticket for Tracy in Texas, since she’ll be able to relax and enjoy her time with her daughter without the extra concern of a mishap. However, for those who prefer staying somewhere a little less grand, there is a wide range of lodging options available, from apartment rentals to B&Bs.

When planning a vacation, compare offers from major providers such as CheapCarribean.com, Jetblue, United Vacations, go-today.com, Expedia, and Travelocity.

There are a slew of deals to other enticing tropical destinations, too. Aruba, with its crystal-clear waters perfect for snorkeling or sailing, is more affordable than ever, with packages starting at $449 (without taxes and fees) for five nights at the Aruban Resort and Casino, round-trip airfare, weather insurance, and $100 refund if it rains. San Jose, Costa Rica, can also be an affordable option for sun, sand, and adventure. Packages start at $369 per person (without airport taxes and fees) for travel through August 12, and include round-trip airfare from Miami (other departure cities available for a higher price), airport transfers, three nights’ accommodations, San Jose city tour, and daily breakfast.

I wish you the best of luck in having a mishap-free vacation, whether you choose Jamaica or some other tropical beach.

As for my other readers: Do you have a place that you believe is better suited for Tracy and her daughter? Have you found a deal that is too good to pass up that you’d like to share? Please let us know by filling in the form below.

Get Help With Your Next Vacation

Let me help you plan your next trip, whatever your budget might be. Submit your request using the form below, and please remember that the more compelling (and specific) your question, the better the chance you’ll be selected for an upcoming case.

Editor’s Note: SmarterTravel.com is a member of the TripAdvisor Media Network, an operating company of Expedia, Inc. Expedia, Inc. also owns Expedia.com.

All prices, dates, and booking details listed here were valid at the time of publication. Some information may have changed since that time.

We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.