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Hotel Holy Grails: The 7 Hard-to-Book Hotels We Can’t Stop Thinking About

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I don't know about you, but I sure didn't grow up staying at five-star resorts on family vacations. But hotel points, free night certificates and travel credits have made it possible for me – and my Thrifty Traveler colleagues – to stay at top-tier luxury hotels we wouldn’t otherwise be able to afford. 

And we help others do the same. In 2024, we officially launched Hotel Alerts – a brand-new add-on to our Thrifty Traveler Premium flight deal alert service. For an additional $24.99 a year, members can opt-in and start getting alerts to book some of the best properties in the U.S. and across the globe to redeem their points from these hotel chains – or transferable credit card points. 

In the months since we launched, we've sent tons of spectacular hotel alerts to help travelers book some of the best properties all over the world this year and next. We're constantly on the prowl for rare award space and getting these deals to our subscribers first.

While we've stayed at a bunch of really cool properties, there are still many we haven't gotten around to yet. Let's take a deep dive into our team's holy grail hotel properties – the ones we’ve booked ourselves and the ones we’re hoarding our points to hopefully book someday.

Curious about how our hotel alerts work? Read all about it!

 

 

The St. Regis Maldives Vommuli

The St. Regis Maldives Vommuli is one of the world's best resorts in the Maldives, surrounded by the crystal blue Indian Ocean. It's also among Thrifty Traveler Co-Found Jared and Lead Operations Manager Erica's favorite hotel stays of all time (check out Erica's review!). 

 

a resort with overwater villas and a sandy beach with a pool
Courtesy of Marriott

 

The location is amazing, the design, thoughtful yet impeccable, and the food, while expensive, is high-quality and delicious. The St. Regis Maldives Vommuli offers personalized luxury service from the moment you step off the plane in Male (MLE) to the second you step through security to, sadly, make your way home.

Oh, and did we mention the personal butler?

 

St. Regis Maldives Vommuli beach villa with square pool, table and chairs and daybed with a patio

 

Jared and Erica were upgraded to a beach villa which grants direct access to the beach and is equipped with a pool right outside of their villa.

 

St. Regis Maldives Vommuli beach villa bedroom interior shot

 

You'll get a private island-like experience. But it's not going to be cheap. Paying cash, you can safely expect to spend at least $2,000 a night, and sometimes much more. If you're aiming for an iconic overwater villa, you can safely double (or sometimes triple) that price. Not exactly thrifty. Unfortunately, even if you use Marriott points, a night could run you upwards of 150,000 points a night on average. Ouch.

 

Maldives and Dubai Hotel Alerts deal email with an aerial property image of the St. Regis Maldives Vommuli Resort

 

Conrad Bora Bora Nui 

The Conrad Bora Bora Nui is absolutely one of our favorite Hilton resorts in the world. In fact, our executive editor Kyle is obsessed. He checked this off his bucket list last year and enjoyed his stay (check out his review!).

 

 

overwater villas with straw roofs in the ocean
Courtesy of Hilton

 

It's one of the ultimate bucket-list properties for Hilton aficionados – and one of the hardest to actually book using points, to boot.

The property is widely acclaimed for its warm service, beautiful grounds, and incredible villas – both on land and perched over the ocean. Kyle got to try both out with a mid-trip, Hilton Diamond status upgrade to an overwater villa.

 

Conrad Bora Bora overwater villa bathroom

 

This resort in French Polynesian paradise regularly charges $900 to $1,200 a night or more for a standard room … and the going rate to book an overwater villa here is typically closer to $2,000 a night.

That makes it a fantastic way to use Hilton Honors points, Hilton free night certificates, or both. But that hinges on standard award availability to actually book this pricey property with points: 120,000 of them per night, to be exact.

 

Conrad Bora Bora Nui Hotel Alert for conrad bora bora nui for 120,000 points. Was $1,200 or more per night.

 

Calala Island

Calala Island is a secluded, all-inclusive resort in the Caribbean and one of the hardest properties in the world to book with points. 

 

an island in the middle of the ocean covered with palm trees
Courtesy of Hilton

 

The all-inclusive Calala Island just got added to Hilton as part of Small Luxury Hotels of the World (SLH) after Hilton pulled off the coup of the year in 2024 when it stole these properties from Hyatt, opening the door for Hilton members to book hundreds of the most impressive boutique properties around the globe using points.

 

bed and a couch inside a hotel villa with an ocean view
Courtesy of Hilton

 

Located off the coast of Nicaragua, Calala is a near-private island experience with your points. You'll stay in one of just a half-dozen villas on the property, all right on the beach. You would book into a Junior Suite, which is quite literally a luxury cabana on stilts sitting right by the water with 360 degree views of the beach. You can fish, snorkel, paddle board, island hop, and even do private rum tastings to your heart's content – and it's all included.

If you are able to find nights, standard awards are bookable for 150,000 points. This is a prized (and nearly impossible) redemption for a property that often costs $4000 or more. You'll need to book at least a 3-night stay … but you should book five or more to get a 5th night free with Hilton status!

 

Thrifty Traveler Premium hotel alerts calala island in nicaragua for 150,000 points. Was $4,000.

 

Waldorf Astoria Seychelles Platte Island

High on Chief Flight Analyst Jon's list is the Waldorf Astoria Seychelles Platte Island. Staying at this property off the coast of Africa will surely make you feel like a Bond villain in your own private beach villa, on a private island in the Seychelles – complete with its own private airstrip – using Hilton Honors points.

 

a hotel room patio with a swinging daybed, private pool and beach access.
Courtesy of Hilton

 

Your points put you into a garden villa that comes with your very own private pool, outdoor shower, and direct beachfront access. Go snorkeling or scuba diving in the incredible reef surrounding the island or treat yourself to a wellness day at the on-site spa. 

 

a hotel bathroom with a circular tub and double doors leading to a patio
Courtesy of Hilton

 

Finding any availability to book free nights on points has been tough but we've found standard award space bookable for 130,000 Hilton Honors points per night, as good as it gets for a top-of-the-line property like this. And considering these rooms are currently selling for more than $2,000 a night, it's an absolutely fantastic way to burn your Hilton Honors points.

 

 Waldorf Astoria Seychelles Platte Island Hotel Alert. For 130,000 points per night. Was $1,3000 or more per night. Booked with Hilton points.

 

Park Hyatt Kyoto

The Park Hyatt Kyoto is a team favorite. Our founders Jared and Nick stayed here in 2023 and Nick gave the property high praise in his review. Our product manager Tracey just stayed here as well.

 

Park Hyatt Kyoto hotel stone driveway and entrance

 

From its picturesque grounds, traditional architecture, elegant rooms, top-tier service, and excellent dining, you'll truly get the five-star treatment with a Japanese flare during your stay here.

 

hotel room with two queen beds, an armchair and small coach and light wood walls.

 

This is one of the hardest properties to book with points in Hyatt’s entire portfolio as they typically don't release a lot of award availability to book with points. Add in the fact that the property only has 70 rooms, and the room inventory that is available to book with points can go quickly.

The Park Hyatt Kyoto is a Category 8 Hyatt property, which means if you're using World of Hyatt points, a standard stay will run you 40,000 points per night.

That may seem steep, but that's as good as it gets for a high-end property like this. And since cash rates are routinely over $1,500 a night, it's an excellent way to use points. Plus, Hyatt's peak- and off-peak award pricing system means you may see rooms bookable for as few as 35,000 points a night – or as much as 45,000 points during busy times.

 

Thrifty Traveler Premium hotel alert for the Park Hyatt Kyoto from 35,000 Hyatt points per night. Was $1,500 per night.

 

Park Hyatt Niseko Hanazono

Going further north, Travel Reporter and Flight Deal Analyst Gunnar has his sights on staying at the Park Hyatt Niseko Hanazono for ski season.

 

Park Hyatt Niseko Hanazono exterior property shot with snowboarder walking
Courtesy of Hyatt

 

Located across the the Annupuri ranges and Mount Yotei, this year-round ski resort is paradise for ski enthusiasts. Bedrooms are spacious with seperate living and dining areas equipped with a second bathroom. The property is equipped with an on-site onsen, golf course, and ski rentals available.

 

spacious hotel room with a full dining room table, couch, and a bedroom separated by a glass wall
Courtesy of Hyatt

 

The Park Hyatt Niseko Hanazono is a Category 8 Hyatt property, which means if you're using World of Hyatt points, a standard stay will run you 40,000 points per night.

That may seem steep, but that's as good as it gets for a high-end property like this. And since cash rates are routinely over $600 to $1,000 a night, it's an excellent way to use points. Plus, Hyatt's peak- and off-peak award pricing system means you may see rooms bookable for as few as 35,000 points a night – or as much as 45,000 points during busy times.

 

JW Marriott Masai Mara Lodge

For a safari on points, you can't top the JW Marriott Masai Mara Lodge. Kyle and Credit Cards and Award Travel Editor Jackson are already thinking about ways to come back to Africa to stay at this property. 

 

a tented hotel suite on the savanna with a private pool
Courtesy of Marriott

 

There are 21 tented suites equipped with a private jacuzzi tub and deck that are situated along the Talek River – seeing wild game right from your room isn't uncommon.

 

hotel room with a large bed with curtains
Courtesy of Marriott

 

With rates starting at 130,000 points per night, it's far from cheap. But once you consider that price includes all your game drives, food, and drinks, it seems a lot more manageable … especially when you compare it to the cash cost, which is routinely north of $3,000 per night. 

 

Thrifty Traveler Premium hotel alert for the JW Marriott Masai Mara Lodge from 122,000 points per night. Was $3,000 or more.

 

Bottom Line

Our team has stayed at some of the best luxury resorts in the world but we still have a lot of hotels still on our bucket lists. We'll be saving our points in the meantime and keeping an eye out for rare award availability to stay at these properties. Be on the lookout for the next Hotel Alerts we send your way.

Lead image courtesy of Hilton


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