tl;dr – A list of compelling travel deal(s) that you might want to consider.
Welcome back to another edition of “Deals I’m Booking That You Should Book Too”, a weekly series where I walk you through three curated (possibly more) random travel deals – points & miles, cash, otherwise (?) – that I find compelling for one reason or another. I’ll try to keep this coming to you every Friday (hopefully 😉). You can find the past installments here. Ok, let’s dive into it.
The Deal
A 5-night Stay So You Can at the Waldorf Astoria Costa Rica Punta Cacique for $2800

Same concept, different tropical destination. I’ve written about this deal in the past when discussing Hilton’s point sales. If you’ve read any of those posts through, then this might be a review.
This points booking takes advantage of the fifth night free on rewards bookings.
This newish property from Hilton has fairly wide open availability for points bookings, and standard rooms will cost you 140,000 points per night. With the fifth-night free deal, you’ll need 560,000 points for your five-night stay.

If you’re starting from zero, once again, I’ve got you. Hilton is almost always selling points with a 100% bonus, and each Hilton Honors member can purchase a maximum of 160,000 points before factoring in the bonus, which amounts to 320,000 total points (with the bonus), for a cost of $1600.

If you don’t have a stash of existing Hilton Honors points, you’d still currently be 240,000 Honors points short.
You could transfer over American Express Membership Rewards points to Hilton at a 1:1 ratio, but that is a terrible use of Membership Rewards points, as you can put them towards far better redemptions.
Instead, you should activate two-player mode. If you happen to be traveling with a family member, friend, or anyone, so long as they are also a Hilton Honors member, you should know that Hilton allows members to transfer up to 500,000 points each year.
Have ‘player two’ pay $1200 for 120,000 Hilton Honors points (with the 100% bonus that will become the remaining for a total of 240,000). Note, this member’s Hilton Honors account needs to have been active for at least 30 days. Once that’s done, then transfer the points over to the account you plan on making the booking from.

The total cost for those 560,000 points? $2800.
The cheapest you’ll find a base level room at the Waldorf Astoria Costa Rica Punta Cacique is for just about $1000, though for most dates the cheapest rooms are around $1300.
So for five nights, you’d be in for at least $5000. If you buy the points, you’re paying $2200 less than the cash rate. Not bad.

If you’re a Diamond Elite, you should receive complimentary breakfast at the property, though admittedly some early reviews seem to suggest that it may just be a credit and or a continental breakfast (unclear if that’s for a lower tier such as Gold Elites).
Alright, tune in next week for another installment. If you have at all found this helpful and would like more of these and other (hopefully) helpful tips, hit the subscribe button below.