A Caribbean vacation does not have to come with a luxury price tag. This is Daily Drop, after all. With the right mix of transferable credit card points, airline miles, and hotel rewards, it’s entirely possible to take a $5,000 all-inclusive trip to Jamaica for under $200 out of pocket.
Here’s a step-by-step breakdown of how to fly to Montego Bay and stay at top-tier resorts using points and how to do it yourself.
Fly to Jamaica with Miles
Montego Bay (MBJ) is Jamaica’s most popular airport, and the good news is that there are plenty of nonstop routes from major U.S. cities. Whether you’re on the East Coast, Midwest, or even further out, chances are good you’ll find a direct flight, and you can often book it with points.
For example, Southwest offers redemptions as low as 8,600 points from Baltimore (BWI). JetBlue, Delta, and United also have competitive rates, like 9,500 Delta SkyMiles or 9,700 United miles from Newark (EWR). But better value often comes from booking through airline partners, like using 16,000 Virgin Atlantic points for a Delta flight, or 4,500 Alaska miles for a short American Airlines hop from Miami (MIA).
If jumping between programs sounds overwhelming, tools like Daily Drop Pro can instantly show the best-value award bookings based on your preferred dates and points balances.
All-Inclusive Resorts With Great Redemption Value
For accommodations, the standout value came from Hyatt’s Secrets Wild Orchid Montego Bay. Brendan booked this Category D all-inclusive resort for 30,000 Hyatt points per night, thanks to Hyatt’s fixed award chart for all-inclusives.
In total, three nights would have cost over $2,500 in cash. Redeeming 90,000 Hyatt points delivered an impressive 2.83 cents per point in value. Hyatt’s separate A–F award chart for all-inclusive properties helps you predict pricing, even during peak seasons.
This redemption also covers two guests by default. If you’re traveling with a friend (or multiple friends), Hyatt gives you a clear chart for the extra points required per night.
Comparing Hilton, Marriott, and IHG Redemptions
Next up was a two-night stay at a Hilton all-inclusive. Unlike Hyatt, Hilton uses dynamic pricing, meaning point costs can vary widely from night to night. This particular stay came out to 200,000 Hilton Honors points (equivalent to 100,000 transferable points), with a cash value of $1,458 (around 1.45 cents per point).
That’s still pretty solid, especially considering Hilton’s fifth-night-free benefit on award stays. Marriott and IHG also offer all-inclusive options in Jamaica, including:
Marriott’s Royalton Blue Waters (around 60,000 Bonvoy points per night)
IHG’s Holiday Inn Resort Montego Bay (about 86,000 IHG points per night)
All three brands offer occasional free-night awards via co-branded credit cards, plus bonus nights for longer award stays, something Hyatt doesn’t currently match.
Travel Credits and Extras
Even with points covering flights and hotels, you’ll still have to cover some costs like taxes, airport transfers, and resort fees. Travel credits from cards like the Capital One Venture X Rewards Credit Card or Chase Sapphire Preferred® Card can help with those charges after the fact.
In Brendan’s case, those extra costs added up to under $200, making it the only out-of-pocket expense for a vacation that would’ve cost over $5,000. So yeah, not bad!
It’s also worth considering whether an all-inclusive resort is the best fit. If you don’t drink or eat a lot, you might get better value by booking a standard hotel for fewer points and covering meals separately.
Final Thoughts
Jamaica is one of the easiest places to maximize your miles and points, with strong airline award availability and a wide variety of resort options across all major hotel brands. Whether you're aiming for a beachfront suite or a quick sunny trip, a smart use of points and miles can give you some serious value.
By using the right booking strategy and stacking travel card perks, a luxury getaway to Jamaica is super doable. And if you’re a visual learner, make sure to check out the video at the top of the article. Happy travels, friends!
