Summer Beach Getaways for Less Than $300

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.

dadig writes, “My wife, son of 5, and I are looking for a safe, relaxing beach vacation during the first week of July. Our top priorities are a clean, safe ocean beach not in disrepair due to hurricanes, an ocean view room right on the beach, and a top notch pool area. We are looking for a four- to five-star resort and would prefer all-inclusive. We are open to traveling in the US, Mexico, Puerto Rico, and [the] Caribbean. Can you recommend a few family friendly places? I have read that now is the time to try to get free room upgrades from the hotels. How would you recommend doing this?”

I couldn’t resist this question because the idea of lying on a warm beach sipping a frosty drink while listening to the waves lap lazily against the shore sounds like heaven right now. And since I can’t be there myself, I can at least help you and your family enjoy a sunny vacation.

If you want to avoid all things hurricane, we’ll have to narrow our search in the Caribbean, as only the “ABC Islands” (Aruba, Bonaire, and Curacao) exist outside of the traditional Atlantic hurricane belt, and July happens to be prime time for wet and windy weather. And though there has been some buzz about safety issues in Mexico’s border towns recently, there’s still an entire country to explore for deals. So, let’s see what we can find there, too

There are three easy ways to search for your trip: let the deals lead you, take a tailored vacation, or go with your destination. Here are examples of each of the different ways, and how you can make them work for you.

Start by searching for sales or deals offered by vacation providers. I found vacations to Aruba through Expedia starting at $555 per person (with taxes and fees). The deal includes four nights’ accommodations and round-trip airfare from Miami (other departure cities are available at a higher cost). The starting rate is also for a two-and-a-half-star hotel, but three- and four-stars are available starting at $594 per person. CheapCaribbean is another place to search for discounts and deals on tropical destinations. The Caribbean is an exceptional place to relax and have some fun in the sun with your wife and little one, especially when you can go at a discounted price. As I stated above, you can skip a lot of the worry about the weather by sticking to the “ABC Islands.”

Next, try searching for specific types of vacations that meet your criteria, such as beach, family, or all-inclusive. Orbitz offers a variety of specials specifically tailored for those looking for a beach getaway in places like the U.S., the Caribbean, and Puerto Rico. Deals range from free nights to savings of up to 50 percent, depending on the destination and resort.

Finally, try searching for a specific destination. For example, if you have your heart set on Puerto Vallarta, begin by tracking down deals there. I priced packages through PleasantHolidays starting at $295 per person (without taxes and fees). The deal includes three nights’ accommodations and round-trip airfare from Los Angeles; kids 12 and under stay and eat free.

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These three tricks are indispensible when planning a vacation, especially one that has so many possibilities. However, in your case, I might also consider taking a cruise; it may not have the beach, but oceanside views are a guarantee.

Regarding your question about hotel upgrades, my colleague and Senior Editor Sarah Pascarella recently covered the topic, and offered a slew of suggestions.

I wish you the best of luck in all of your vacation pursuits, and I hope you have a cold drink for me.

If any of you other readers have suggestions on where dadig should take his family for a beachside escape, please leave a comment below.

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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.