Best Tropical Family Vacations from the U.S. w/ Credit Cards Rewards & Points

Happy Family of Four on Tropical Beach
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You’re probably familiar with many of the best tropical family vacations mentioned below. After all, these locations have been listed repeatedly on the big-name sites.

What you might not know is that families can travel to most of these locations for free using credit card rewards.

Read below for a quick primer on how to take your next family vacation for free using credit card rewards. Or just use the table of contents (below) to skip down and discover the eight best family-friendly tropical vacation destination from the U.S.

Redeeming Credit Card Rewards 101

If you’re new to using credit cards for free travel, often called travel hacking, the idea is to earn credit card reward points (or miles) and exchange them for free or heavily-discounted flights, hotels, Airbnb rentals, and sometimes even experiences like theme park tickets.

Credit card companies offer points as a way to encourage us to use credit cards more. And when you consider the billions of dollars banks make off interest payments, the strategy works.

However, for someone that understands how credit cards work and never carries a balance, it’s possible to use this to our advantage.

The art of redeeming credit card rewards for travel can get complex. Nonetheless, there are simple strategies that can save beginners thousands of dollars on any trip.

If you’re looking to take a deep dive into the world of redeeming credit card points for travel, check out my ultimate travel hacking guide — it will teach you all the tips, tricks and strategies you need to know.

If you’re not ready to take the plunge, here are a few basics to know.

First, there are four primary ways to use credit card rewards to book flights and hotels.

  • Airline and hotel loyalty programs. Most major hotels and airlines have their own co-branded credit card. An example of a co-branded card would be the Southwest’s Rapid Rewards Premier Card. With this card, your purchases earn points that get deposited into your Southwest Rapid Rewards account, which you can then redeem for Southwest flights.
  • Transfer points to airline loyalty programs. Flexible reward programs, like Chase Ultimate Rewards, allow you to earn points inside of the program then transfer these points to their transfer partners. For example, you could earn points via Chase Ultimate Rewards and then transfer them to Southwest.
  • Fixed-value rewards. Fixed-value rewards are convenient for beginners because they allow you to “erase” travel expenses from your credit card statement. For example, you might be able to apply 50,000 points to your statement to wipe away a $500 charge from a hotel purchase.
  • Travel portals. Credit card companies have their own travel portals, such as Chase Ultimate Rewards, which allow you to purchase travel using points.

Second, the best strategy for earning a lot of points quickly is taking advantage of available sign-up bonuses. Then, by utilizing bonus categories to make sure you’re maximizing your points for each purchase. For example, with the Chase Sapphire Preferred Card, you can earn 2X points on dining and travel purchases.

While you can choose to earn rewards through either a co-branded credit card or through flexible reward programs like Chase Ultimate Rewards, keep in mind that flexible rewards cards allow you to transfer to a number of different loyalty programs, so it’s typically best to prioritize flexible cards over co-branded cards when you’re just getting started.

Ready to see where rewards can take you?

Here are eight tropical family vacations you can take using credit card rewards. For each destination, I highlighted a different strategy for saving money on your trip. Read through each destination (even if you’re not wanting to go there) to arm yourself with the tactics and strategies for saving money.

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#1 — Kauai, Hawaii

Known for: Kaui has been hands-down my favorite family travel destination. I specifically love Princeville, which is located on the north side of the island, not far from the famous Napali coast. The sunset above is a photo I took from Ke’e beach, which is the trailhead for the world-renowned Napali Coast hike.

How to fly to Kauai with points: For those on the west coast, flying across the Pacific to Kauai is a lot easier. An airline with multiple non-stop flights to Kauai is Alaska. Not only is there a co-branded Alaska Airlines credit card, which has a decent sign-up bonus, but Marriot is also a transfer partner of Alaska Airlines, which gives you the opportunity to earn points for this trip via the Marriott Bonvoy Boundless personal card or the Marriott Bonvoy Business card.

Compare the Marriot Bonboy Boundless personal card to other top travel cards.

Where to stay: If you’re staying on the north side there aren’t many options, and the largest beach resort — the St. Regis — is not available in any loyalty programs when I last checked. My recommendation is finding an Airbnb in Princeville or Hanalei using fixed-value rewards.

If you decide to stay on the south side of the island (making sure to plan at least one day-trip up north), Popai is a popular town with a few resort options. One is the Grand Hyatt, which costs 25,000 points per night through the World of Hyatt program.

You can transfer Chase Ultimate Rewards to Hyatt at a 1:1 ratio, allowing you to book five nights for 125,000 total points.

A good card to look at then would be the Chase Sapphire Preferred. There’s also the World of Hyatt Credit Card, which has another solid sign-up bonus. Combine the two bonuses together and you’re not far from five free nights.

#2 — Costa Rica

Known for: Secluded beaches, tropical rainforests and amazing wildlife. Also, it’s quite affordable compared to some of the more popular destinations.

How to fly there: When flying with my three kids, I first use Google Flights to check which airlines offer direct flights to my destination. If none are available, I’ll see which airlines offer the lowest total travel time. From there, I can start to narrow down my options and see which airlines I should focus on.

During my research for this article, I couldn’t find any non-stop flights. However, I did find that American Airlines offers a lot of options for getting to Costa Rica. American Airlines’ loyalty program is part of OneWorld, which means I can potentially book an American Airlines flight using points from any airlines that participate in the program.

One such airline is British Airways. Points are fairly easy to earn with BA, as they offer a credit card with a sign-up bonus. There are also two flexible reward programs (Chase Ultimate Rewards and American Express Membership Rewards) that list British Airways as a transfer partner. As a rule of thumb, I prefer earning points in transferable programs like Chase Ultimate Rewards and American Express Membership Rewards.

So, now the question comes down to how many points I’ll need to earn, as well as availability.

A round-trip ticket from Chicago to San Jose runs 25K points per person for a saver award (which is the lowest cost award redemption the airlines offer). With that in mind, I’d run down the list of top credit cards for travel to see my best options for earning points from either Chase Ultimate Rewards or American Express Membership Rewards.

Where to stay: One of my favorite ways to book hotels is through Chase Ultimate Rewards. As I have the Chase Sapphire Reserve card, points are worth 50% more when booking a hotel through CUR. With a quick search, I find plenty of affordable kid-friendly hotels with amenities for all ages (including swimming pools) in Guanacaste (one of the more popular beach towns in Costa Rica), including two that are on sale:

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This is where the Chase Sapphire Reserve really shines. As the points are worth 50% more, the sale price brings the room down to just 17,729 points per night for a high-end hotel.

Also worth checking out within Chase Sapphire Reserve are the room options. For the Hotel Riu Palace, there’s a two-bedroom family suite costing just 30,000 points per night.

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#3 — Riviera Maya, Mexico

Known for: Close proximately to the U.S., all-inclusive resorts, and beautiful beaches with powdery white sand.

How to fly there: One useful travel hacking tool is AwardHacker. The site allows you to search awards flights and see which airline costs the least amount of points.

Searching AwardHacker, I find that Singapore Airlines’ KrisFlyer program allows you to book a flight from Chicago to Cancun for just 15K for a round-trip ticket (the flight is operated by Alaska Airlines and includes one-stop)

AwardHacker Screenshot

You can learn more about how to use AwardHacker in my in-depth review of the site.

Another tip that’s useful here for those in the southern part of the U.S. is that British Airways operates on a distance-based awards chart. (Remember, British Airways is part of the OneWorld alliance, so while you’re booking flights through British Airways you’re flying U.S.-based airlines). Flights from Miami or Texas, for example, which are in relatively close proximity to Cancun, run just 15K points for a non-stop round-trip flight.

Where to stay: The simplest method for booking reward trips is with fixed-value rewards. Using fixed-value rewards essentially allows you to use points to erase a travel charge. For example, with 50,000 points, you can erase a $500 travel charge.

The two most popular fixed-value programs are Capital One and Barclays. My preference is Capital One, as they have a wider selection of cards for earning points and the ability to transfer points to airlines.

Using fixed-value rewards allows me to choose from any number of hotels or opt for an Airbnb. And when I look at the options on Airbnb, there are 20+ Airbnb Plus verified homes operated by Superhosts (which I prefer to stick with when traveling internationally).

#4 — St. Barts, The Caribbean

Known for: Small, high-end Caribbean island resort destination with picturesque, crystal clear water and white sand beaches.

How to fly there: Getting to St. Barts isn’t easy. You’ll have to fly into Sint Maarten, where you’ll catch a shuttle flight or take a ferry to St. Barts. The ferry will be your cheapest option, but still runs $60+ per-person each way.

Fortunately, there are a lot of options for getting to Sint Maarten.

One technique I like to use for booking rewards trips is to find the lowest prices on flights through Google Flights.

Researching for this article, I find that when flying from New York to Sint Maarten there are a number of airlines to choose from:

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And just as my points are worth 50% more with the Chase Sapphire Reserve Card when booking hotels, they are for flights as well. This comes in handy when there’s a great deal on a flight, as instead of booking by transferring points you can book right through Chase Ultimate Rewards. The other advantage here is that there’s typically better availability.

(If you’re not willing to pay the fee for the Chase Sapphire Reserve card, consider the Sapphire Preferred, where your points are worth 25% more when redeeming them for travel.)

When I log in to Chase, I see that the nonstop flight on Delta is listed for just 24,697 points:

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Note: You may be able to get this flight for less by transferring points to British Airways. However, I wanted to highlight the strategy of finding the lowest deal via Google Flights then booking with Chase Ultimate Rewards.

Where to stay: As St. Barts is a smaller island, many of the major hotel chains and loyalty programs don’t have a property available. As such, your best bet is likely using fixed-value rewards.

For example, if you were to accumulate 100,000 points through Capital One, you could get the below hotel for four-nights at no cost.

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And while this sounds like a stretch, one aspect of the Capital One rewards program is that you can transfer your points to anyone. As such, with the current sign-up bonuses offered by Capital One, all it would take is for both you and your spouse to earn the bonus.

Compare the top Capital One cards available today.

#5 — Ambergris Caye, Belize

Known for: Belize Barrier Reef, a world-renown 370 square-mile reef that offers up-close views of ocean wildlife and world-class scuba diving in stunning blue waters.

How to fly there: So far, I’ve highlighted the most common ways to book an awards trip. But what if you want an upgraded experience — anything from first class to premium economy?

One key to landing first class flights is booking a “saver” award. Most airlines have two types of award tickets:

  • Any time: Any time rewards cost more points to book but there are more possible flights.
  • Saver: Saver awards are discounted rewards tickets offered by an airline, usually during non-peak travel season.

The terminology for “any time” and “saver” awards tickets change per airline, but it’s important to understand that getting to your destination using a saver award often costs about half the points.

Below you can see the award available for business or first class seats on American Airlines from Miami.

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At 25K points for a one-way ticket, it certainly becomes doable to book an upgraded flight. To build up points, I’d look into the Marriott Bonvoy Boundless card, which allows you to transfer points to American Airlines at a 3:1 ratio. And if you’re really looking to rack up the points, consider the sign-up bonus on an American Airlines branded card like the Citi/AAdvantage Platinum Select World Elite Mastercard.

Where to stay: A Hilton property worth looking into is the Mahogany Bay Resort & Beach Club. Rooms can be booked at this high-end resort for as little as 59,000 points per night.

American Express is a transfer partner of Hilton, where one Amex Reward point can be transferred for two Hilton Honors points. There are both a number of decent American Express sign-up bonuses available, as well as a Hilton co-branded card.

#6 — St. Kitts and Nevis, The Caribbean

Known for: Small Caribbean island with a rare combination of mountains, rainforests and beaches.

How to get there: The most common route to St. Kitts and Nevis is through Miami on American Airlines. A round-trip ticket for me is currently 30,000 points, with a fair amount of availability.

If your family has a flexible schedule, one tool I recommend for finding cheap flights and/or awards space is Google Flights’ price graph. This allows you to see prices ranges of flights for up to three months at a time.

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Saver award tickets typically correspond with cheap flight prices. As such, this is a good tool to get a general idea of when you should take your trip.

Where to stay: One of my favorite hotel rewards programs is Marriott’s. There are both personal and business cards available to earn Marriott points with great sign-up bonuses. Plus, you can transfer points from Chase to Marriott. But one unique feature of Marriott is that you can book your stay before you have the points, using Marriott Advance.

Say you want to book the St. Kitts Marriott Resort & The Royal Beach Casino, which has rooms for as little as 35,000 points a night for a trip that’s six months away. You can reserve your room today, then over the next six months accumulate the points needed to pay for your trip.

See top hotel credit card offers currently available.

#7 — Tulum, Mexico

Known for: A favorite of those looking for a relaxing beach vacation, Tulum offers long stretches of beaches as well of the ruins of an ancient Mayan port city.

How to fly there: As with Riviera Maya, when you’re flying into Tulum you’ll go through Cancun.

While we covered the flight options above, one tip I’ll highlight is that when there’s a great sign-up bonus available, one advantage couples have is that they can both earn that bonus. Furthermore, some reward programs allow you to combine points with one member of your household. For example, with Chase, you could both earn the sign-up bonus for the Chase Sapphire Preferred and then combine this into one account.

Where to stay: The ability to combine points with one account opens up some creative travel opportunities for families. One favorite of mine is the Chase Trifecta.

This is when you earn points via the:

  • Chase Freedom, which offers 5X bonus categories (on up to $1,500 in spending per card anniversary year) that rotate quarterly
  • Chase Freedom Unlimited, which gives you 1.5% cash back on all your purchases

Then, combine these points into one Chase Sapphire Reserve (where points have more value).

Note: I explain this method in more detail here.

From there, you can book through the Chase travel portal using your Chase Sapphire Reserve card, which has plenty of options in Tulum:

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See Also: 10 Best Ways to Find Cheap Hotels

#8 — Key West, Florida

Known for: A Caribbean-like feel that’s drivable from the mainland U.S. and offers a bevy of water sports options.

How to fly there: While there are certainly a number of ways to fly to Key West, I wanted to include at least one possible road trip on this list of best tropical family vacations.

Road trips save you money not only on flights, but also on car rentals at your destination. If you’re on a tight budget, they’re a great way to go.

Where to stay: While there are a number of hotel options, there are also hundreds of vacation rentals in Key West on Airbnb. I’d therefore focus on accumulating fixed-value rewards with Capital One or Barclays and using them to book an Airbnb.

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If you do drive, this can make for a very cheap vacation.

See also: Best Family Vacation Ideas & How to Take Them for Free

Summary: Best Tropical Family Vacations from the U.S.

I’ve been playing the points game now for years. It’s saved my family thousands of dollars, and more importantly, has given us experiences we wouldn’t have been able to have otherwise.

If you’re new to the idea, just be patient and start simple. A card like the Chase Sapphire Preferred, which is the card I most recommend for beginners, can help you save money in a number of ways. Even easier is using fixed-value rewards with a card like the Capital One Venture Rewards Credit Card.

R.J. Weiss
R.J. Weiss is the founder and editor of The Ways To Wealth, a Certified Financial Planner™, husband and father of three. He's spent the last 10+ years writing about personal finance and has been featured in Forbes, Bloomberg, MSN Money, and other publications.

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