🇨🇷 How We Saved $10,000+ on a Luxury Trip to Costa Rica

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Today, 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 Certs

Our journey to six free night certificates started with a strategic approach, leveraging Hilton Honors co-branded credit cards. 

• Hilton Aspire Card: The Hilton Honors American Express Aspire Card gives you Hilton’s Diamond status right out of the gate (that’s their top tier). It also comes with an annual free night, a $200 Hilton Resort credit every six months, a $50 quarterly airline credit, and other perks. Yes, it has a $550 fee, but when you add it all up, it’s not hard to come out way ahead.
• Hilton Surpass → Upgrade Play: The Hilton Honors American Express Surpass® Card has a $150 fee and gives you Gold status and quarterly Hilton credits. It also earns a free night after $15K spend. We hit that spend, then upgraded it to an Aspire, which not only gave us the Aspire’s better benefits but also triggered another free night certificate. On top of that, after hitting $30K spend total, we earned a second cert.

Between the anniversaries on our Aspires and a Surpass welcome bonus that came with a promo certificate, we were sitting on six free night certificates. What makes these free night certificates so powerful is that they work at almost any Hilton worldwide, including top-tier properties like Conrad Bora Bora or Waldorf Astoria Maldives, as long as a standard award room is available.

🏝️ Choosing Our Destination

Once we had the free certificates secured, the question became: where do we burn them for maximum value?

• 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–$1,900.

🏨 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 720K points drops to 600K with the Fifth Night Free perk. At 0.5¢ each, that’s ~$3,000 total for a stay that would cost $9,000+ in cash (about 66% 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 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.
• Booking & Upgrade Experience: Booking certificates required a phone call, and because of how the system works, we had to split into two back-to-back 3-night reservations but the hotel was able to link them. Thanks to Diamond status, we also got bumped from a Garden View to an Oceanview room. When our first room had AC noise, the front desk (shout-out to Tiera) moved us to an Oceanview suite, which ended up being one of the best rooms in the hotel.

🛏️ 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.

ADD PHOTOS

• 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 plus eggs and coffee drinks — 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 “Luko Fusco” and “Vita” were standouts. There’s also a gelato shop and fun mocktail options.
  • Dinner: La Finca was a highlight, and the lobby bar was perfect for sunsets. We also loved the room-service churros.
• 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 (AC noise, phone system), 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: So 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 a similar flight 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. This saved us 60,000 points compared to the original higher-priced business class option.
• Flight Experience: The United economy flight was a standard 6.5-hour experience. The domestic business class flight home offered bigger seats and a better meal, but was on an older plane, not comparable to long-haul international business class. The Alaska Lounge at LAX was a great spot to relax during our layover.
• 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 looking into two options. 

• Sensoria: Booked through the concierge, this private property offered trails and thermal pools about 2.5 hours away (4WD required). The scenery was beautiful, though our guide wasn’t a great fit. Still, it’s worth it for the hike if you’re nearby, though for serious wildlife viewing, you’re better off in La Fortuna or the Osa Peninsula.
• Diamante Eco Adventure Park: A busier but super fun outing with a mile-long ocean-view zip line, 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.

💎 Pro Tips for Your Next Luxury Getaway

Even if you're not going "all in" on points and miles, there are ways to enjoy luxury perks. 

• Premium Credit Card Hotel Programs: Many premium credit cards, like  Amex's Fine Hotels + Resorts or The Hotel Collection, The Edit by Chase Travel, or Capital One's Premier Collection, offer benefits like free breakfast, upgrades, property credits ($100 per stay), early check-in, late check-out, and welcome amenities at luxury hotels, even without elite status.
• Travel Agents: Booking through a knowledgeable travel agent can also secure these perks and often gives you higher priority for upgrades due to their direct relationships with resorts. Look for agents partnered with networks like Virtuoso or hotel-specific programs such as Hyatt Prive or Four Seasons Preferred Partners.
• ATH Hotel Upgrade Program: We've built a luxury hotel search tool (password: perks) that allows you to book these rates with all these luxury perks (including free breakfast for two, $100 property credit, room upgrades, early check-in or late check out) yourself, bypassing the need for phone calls or emails.

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.