How I Booked a $10,000 Hotel Stay in Grand Cayman for $400

Grand Cayman is a great destination for a family vacation. It’s easy to get to, the beaches are beautiful, and there are lots of fun activities.

However, it also tends to be one of the more expensive Caribbean islands, so a vacation there isn’t necessarily cheap. But, of course, we can make it much more affordable using points and miles!

I took a 5-night luxury family vacation on the island of Grand Cayman and paid only $400 for my hotel which would have otherwise cost over $10,000. Yes, you read that right!

In this post, I’ll show you exactly how I did this and how you can do it, too.

A $10,000 Grand Cayman Hotel Stay for $400

The hotel I chose was actually the entire reason for this trip. I had written a post about the best Kimpton hotels to book with points, and I was so intrigued by one of the properties on that list that I had to book it.

Kimpton Seafire Resort & Spa is located on Seven Mile Beach on the island of Grand Cayman. This luxury beach resort is expensive but can be a great deal on points.

My trip was during spring break, so cash rates were exceptionally high. The cost of a base level 2 Queen Premium Ocean View Room was $1,831 per night during my stay. In addition to the room charge, there was a 10% service charge and an $80 resort fee, making the room cost over $2,000 per night. Wow!

Hot Tip: This hotel doesn’t always charge so much, but it’s never cheap. During low season the cost can drop to about $700 per night, giving you 1 cent per point in value when you pay with points. Considering we value IHG One Rewards points at ~0.5 cents each, you’ll still get good value from your points even when the cash cost is “low.”

Of course, I would never pay that much for a hotel room thanks to my obsession with interest in points and miles. Luckily, the same room only cost 70,000 IHG One Rewards points per night.

Even better, I have the IHG One Rewards Premier Credit Card, so I got the fourth award night free!

Unfortunately, IHG doesn’t waive resort fees as Hyatt and Hilton do, so I still had to pay the $80 per night resort fee. The resort fee was also charged on the free fourth night I got from my credit card.

While I’m not a fan of paying high resort fees, I loved this place, so it was 100% worth it. Check out my full review of the Kimpton Seafire Resort + Spa for all of the details about this property.

So for my 5-night stay, the cash cost would have been over $10,000, yet I spent 280,000 IHG One Rewards points plus $400 in resort fees. That’s 3.6 cents per point in value — about 7x more than what IHG One Rewards points are typically worth.

Hot Tip: Interested in other properties that are an incredible value for your points? Check out our guide to the best ways to redeem IHG One Rewards points for maximum value.

How I Earned 280,000 IHG One Rewards Points

Before this redemption, I had exactly close to 0 IHG One Rewards points. To earn the 280,000 points I needed, I turned to credit cards, of course.

My original plan was to book 4 nights, so I needed 210,000 IHG One Rewards points (the fourth night was free thanks to the IHG Premier card).

First, I applied for the IHG Premier card when the welcome offer was 140,000 points (this has since changed). Then, I used that card to pay for a stay at Kimpton Hotel Monaco Philadelphia which earned 7,656 points. I also earned an additional 19,525 points from that stay by being an IHG One Rewards Platinum Elite member (another excellent perk of the IHG Premier card) and taking advantage of a promotion.

After adding in the points I got from other spending on the card to earn the sign-on bonus I had about ~183,000 IHG One Rewards points. I transferred the extra 27,000 points I needed from my Chase Ultimate Rewards account to get to my original goal of 210,000 points. I normally don’t recommend transferring points from Chase to IHG One Rewards, but I knew I would be getting a high cents-per-point value so I went ahead and did it even though it goes against my standard advice.

After that, I had enough points to book 4 nights at Kimpton Seafire Resort + Spa.

However, because of a flight change, we decided to book an extra night. Instead of trying to earn more IHG One Rewards points or transferring more over from Chase, I booked the night from my husband’s account using his points. He had previously gotten the IHG Premier card when the welcome bonus was 150,000 points, so he had plenty of points to pay for an extra night.

Bottom Line: I earned most of the 280,000 points I needed from an IHG One Rewards credit card, then I topped off my IHG account with some points that I transferred over from Chase Ultimate Rewards. While that’s usually not a great way to use Chase points, I knew this redemption had a high cents per point value so it was worth it to me.

Flights to Grand Cayman via American Southwest

My go-to airline is usually Southwest because I have a Companion Pass that lets me bring a companion on any flight and I just have to pay the taxes and fees ($5.60 each way for a domestic flight; ~$50-$100 for an international flight).

However, when we were looking at flights, Southwest didn’t have any flights during the time we were going (the Cayman Islands still weren’t open to tourists when I was booking the flights in late 2021), so I ended up booking an award redemption through American Airlines.

I originally paid 32,000 American Airlines miles for flights that would have cost $545 each. That was going to give me a 1.7 cents per point value, which is solid, but not mind-blowing. I was flush with AA miles at the time, so I figured I might as well use them and save the cash.

Well, our American Airlines flights got canceled, so I rechecked Southwest, and thankfully flights had been added, so I was able to book through Southwest. Unfortunately, I was still in the process of earning my Companion Pass at the time so I had to get creative.

Our Companion Pass was going to be in my husband’s name with me as the companion, so I booked flights for my husband and daughter first. Then I booked a separate ticket for myself (with the plan to cancel once I earned the Companion Pass). I did this to ensure the flight didn’t sell out and leave me out of luck. It did end up selling out, so I was glad I made this move. After I earned the Companion Pass I called Southwest to have my ticket canceled and to be added as the companion on my husband’s ticket.

I paid for the flights with Rapid Rewards points I had earned from multiple Southwest Airlines credit cards. Southwest Rapid Rewards points have a fairly fixed value, so you’ll always get ~1.3 cents per point.

Bottom Line: There are many ways to fly to the Caribbean with points and miles. I ended up choosing Southwest to utilize my Companion Pass.

Final Thoughts

A family vacation to the Caribbean is a great way to relax and recharge — especially if it doesn’t cost a ton. The great news is that you can still enjoy a luxury family vacation without spending a lot of money.

While I did spend $400 out of pocket for this hotel (stupid resort fees!) it was such a great deal and I absolutely loved the resort, so I was okay with it.