🇨🇷 Saving $10,000+ on a Costa Rica Trip

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I want to walk you through how we saved over $10,000 on a recent luxury trip to Costa Rica, booking a $2,000-a-night Oceanview suite at the brand new Waldorf Astoria for effectively under $300 a night. This isn't just a trip review; I'm breaking down the exact strategies we used to make it happen, showing you how to maximize savings with cards, credits, elite status, points, and smart booking tactics.

Our entire trip was inspired by six Hilton free night certificates we had accumulated. We'll explore how you can achieve similar, if not the same, deals (effectively 65% off a five-star hotel), whether you have Hilton points, Amex points, or are even paying in cash.

Note: I also recorded a full podcast episode on this entire topic that you can listen to here or if you want to see me share share my screen as I do some searching/booking, you can watch the video version below (check out Ep #244 for the audio version). 

🤩 The Inspiration: Free Night Certificates

Hilton's free night certificates are amazing, because they work at any tier property, like the Conrad Bora Bora or Waldorf Astoria Maldives, as long as a standard award room is available. The primary way they are earned is from Hilton co-branded credit cards. 

• Hilton Honors American Express Aspire Card: This card gives comes with an annual free night certificate and another free night certificate after spending $30k and $60k. It also gives you Hilton Diamond status right, a $200 Hilton Resort credit every six months and more.
• Hilton Honors American Express Surpass® Card (Upgrade Play): The card comes with a free night certificate after $15k spend. After hitting that spend, we upgraded it to an Aspire, which triggered another free night certificate. The $15k spend also counted towards hitting $30k for another free night on the Aspire.

Between having two of these cards and meeting the $15k and $30k spend on each, we were sitting on six free night certificates. 

🏝️ Choosing Our Destination

Knowing we had these certificates, the question became: where do we use them for the best vacation?

• Award Search Tools: I leaned on Rooms.Aero and its “Explore Hilton” feature. That let us filter by brand and quickly see which Hiltons had award space. I focused on the Waldorf, Conrad, and SLH brands since we wanted a true luxury stay without the kids.
• Why Costa Rica? We considered other properties, but the new Waldorf Astoria Costa Rica Punta Cacique jumped out. It had wide-open availability, lined up perfectly with our dates, and Costa Rica was a place Amy hadn’t been. It felt like the right mix of “new and exciting” plus maximum redemption value.
• The Math: Standard awards were 120k points per night. Six nights in a garden view room priced out at $9,041 after tax (~$1,507/night). Thanks to Diamond upgrades, we ended up in an Oceanview suite that would’ve been ~$1,960 a night. In other words, each certificate was saving us $1,500–$2,000.

🏨 Maximizing Our Stay

Don't worry, even if you don't have free night certificates, there are ways to play this game.

• Buying Points Instead of Paying Cash: Hilton regularly sells points with 90–100% bonuses, which brings the cost down to ~0.5¢ per point. A six-night stay requiring 600k points drops to 480k with the Fifth Night Free perk. At 0.5¢ each, that’s ~$2,400 total for a stay that would cost over $7,500+ in cash (~70% off).
  • 💡 Tip: Open a Hilton Honors account early, since you may need 30–90 days before you’re eligible to buy points. You can also share points for free, transfer Amex points to Hilton at 1:2, or pick up a Hilton card with a big welcome bonus.
• Status Is Key: Hilton status gets you free breakfast, better upgrade chances, and the Fifth Night Free. The Aspire makes Diamond automatic, but you can also get status through the The Platinum Card® from American Express or by doing a status match.
• Stacking Hotel Credits: We layered on a bunch of statement credits:
  • Two Aspire cards → $200 Hilton Resort credit every six months each.
  • Three of The Business Platinum Card® from American Express → $50 Hilton credit quarterly each.
  • Plus, my dad let us use his expiring Aspire credit.
  • In total, that gave us ~$1,500 in credits, which covered food, drinks, spa, and extras.

🛏️ The Stay at Waldorf Astoria Costa Rica 

This was one of the nicest properties I’ve stayed at, and it’s clear Hilton put serious thought into it.

• Location: On its own private peninsula on the Pacific coast, about 30 minutes from Liberia airport, with 270° ocean views.
• Rooms: Modern and warm, with floor-to-ceiling windows, oversized patios (with outdoor tubs), and big rainfall showers. I loved the glass water bottles for refills.
• Pools & Amenities: Eight pools plus four hot tubs (and more in the spa). There’s a kids club, teen club, outdoor playground, and even free sunscreen, aloe, bug spray, kayaks, and snorkel gear. If we had brought the kids, they would’ve been in heaven.
• Dining: Honestly, the food was so good and credits covered so much of it that we only ate off-site once.
  • Breakfast: Free with Diamond status. Great buffet — don’t miss the hot sauce.
  • Coffee Lab: My favorite spot on the property. Try the “Spice Bliss” turmeric-ginger espresso.
  • Drinks: Cocktails like the “Lusco Fusco” and “Vida” were standouts.
  • Dinner: La Finca was a highlight, and the lobby bar was perfect for sunsets.
• Service: The staff was fantastic. Everyone went above and beyond to make the stay memorable, and being able to leave tips directly on the folio for specific staff made it easy to show appreciation without carrying cash. It’s a brand-new property, so there were minor hiccups, which the staff was able to resolve.

🛫 How We Got There

Booking our flights involved a mix of points and strategic rebooking.

• Initial Search: We started our flight search on Google Flights with the Points Path browser extension installed.
• Outbound Flight: We found a United non-stop flight from San Francisco to Costa Rica for just 20,000 points plus $79 (compared to a cash price of almost $600).
• Return Flight Strategy: The non-stop return flight only operated on weekends, and we were coming back on a weekday. We initially found a business class option from Liberia (LIR) to San Francisco (SFO) via LA for 57,500 points.
• Alerts & Rebooking: I set alerts using AwardTool (you can get $20 off annual plans with code ALLTHEHACKS), and three days before departure, American Airlines dropped the price of ourflight from 57,500 to 27,500 points. We rebooked, with a small caveat: the discounted business class ticket was only available to LAX, not all the way to SFO.
• LAX to SFO Solution: To bridge the gap, we found a Southwest flight from LAX to SFO for 10,500 Southwest points. Thanks to having a Southwest Companion Pass, we effectively got two flights for that price plus $11.20 in taxes and fees.
• Total Flight Cost: Our flights, which would have cost around $1,000 for coach or $2,500 for business class, ended up being a total of 52,750 points per person plus about $145 in taxes and fees. We valued this at roughly 2.60 cents per point redemption.

🛻 Exploring Costa Rica

We rented from Adobe Rent a Car at Liberia airport, and they were fantastic. If you’re planning to explore beyond the resort, definitely get a 4WD since many roads are unpaved. We also appreciated that returning the car half-full came with only a small penalty.

In terms of excursions, we waited until arrival to see what we felt like doing but ended up only doing two excursions. 

• Sensoria: Booked through the concierge, this private property offered trails and thermal pools about 2.5 hours away (4WD required). The scenery was beautiful and I'd recommend a visit. However, next time I'd love to spend a few days near La Fortuna or on the Osa Peninsula to see a bit more wildlife.
• Diamante Eco Adventure Park: The highlight was a mile-long ocean-view zip line, but the also had several canopy runs and a wildlife sanctuary (sloths, birds, and more). It’s touristy but well-run and a great option, especially for families with older kids.

🤑 The Total Cost Breakdown

Here's the breakdown of our amazing Costa Rica trip. 

• Flights: 110,000 points + $145 in taxes for two people.
• Hotel: Six Hilton free night certificates.
• On-Property Spend (Food, Drinks, Spa): $1,500 in Hilton credits used.
• Out-of-Pocket (Car Rental, Excursions, etc.): Approximately $1,100.

Our total out-of-pocket cost for this trip was about $1,100. For what we estimate would have been a $14,000 to $15,000 luxury vacation, this represents incredible value. This was easily one of our best redemptions yet, and the best part is that most of the strategies are repeatable. With the right cards, points, and timing, you can pull off the same play anywhere in the world.

Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.