(EXPIRED) Wild Hotels.com private island promo

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Update 10/27/20: Just a quick reminder that this goes live at 10am ET.


We get emails all the time from marketing folks telling us about promotions, but we rarely write about a promotion that isn’t going to be relevant for at decent segment of our readers. I generally don’t bother writing about most contests since so few people will win. However, Hotels.com’s marketing team has been knocking it out of the park this year. I don’t understand how they haven’t all gotten hired away by someone with deeper pockets at this point. That’s no knock on Hotels.com — I am just impressed by their creativity and how starkly it stands in contrast to promotions like “2500 bonus points per night” or “10,000 points after you stay two nights”.

Get this place for three hundred bucks a night and I can guarantee you will suddenly have more than five friends. Who will make the cut?

Their latest home run is called “Friendsgiving Island”. They are offering a deeply-discounted 7-night stay at a home on a private island off the coast of Florida, complete with a private chef to cater your “Friendsgiving Dinner”. Here is a direct link to the promotion landing page and here is the explanation directly from the press release:

In 2020, spending time with your friends IRL is something to really be thankful for. Hotels.com is here to give your quaran-team the ultimate Friendsgiving upgrade.

The travel site is offering a week-long escape to a vacation home bubble on “Friendsgiving Island” – an entirely private island off the coast of Florida.

  • The seven-night stay includes a 3-bed, 2-bath, 5,000-square-foot vacation home with a veranda, kayaks, paddleboards, a boat dock & helicopter launch pad.
  • Hotels.com is also taking care of Thanksgiving dinner. Your reservation comes with a one-night private chef who will cook the ultimate Friendsgiving for your crew.
  • The property accommodates six guests total.
  • This stay would typically run you $1,400 a night, but Hotels.com is offering it at mega-discounted rate of less than $50 a night, per person (because it’s 2020 and you’re worth it).

Friendsgiving Island is available on a first-come, first-served basis beginning Tuesday, Oct. 27 at 10 a.m. ET.

At $2,000 plus tax for the week, it still isn’t a cheap week away, but holy cow does it look awesome. Here are pictures:

That last pic above might remind you of the awesome road trip robe promotion that Hotels.com offered over the summer. There were only ten available, but see the comments of our post — it looks like not one but two Frequent Miler readers got those robes! Despite the long shot nature, it is indeed possible to win big with Hotels.com on these promos apparently.

And so, yet again, Hotels.com has ensured that I have set a reminder in my phone to sit at my computer in the field in front of my house where I get 5G reception on my phone so that I can refresh like a madman and try to score this deal. Here is the link again.

I’m not even kidding. This was my setup to try to get a road trip robe.
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Larry K

Did you end up going for it, Stephen?


Hmm… disappointing promo when it was never perfectly clear how to try to win.
Tried booking those dates at 9:59am, 10:00am, and 10:01am. Showed the same “not available” all 3 times. So I guess we lost and someone else won?

I feel like they could have designed this a little better. Oh, well. Thanks for sharing and letting us dream a little bit.

Last edited 1 year ago by Tyler

Was this an April fool’s joke or did they just bail on the promo? The landing page doesn’t work for me.

Greg The Frequent Miler

Maybe it was down last night but it works for me now

Captain Greg

Nick, if you beat me to it and are looking for a friendly captain to stay with you and shuttle you back and forth, I know where you can find one 😉

[…] Wild Hotels.com private island promo (Expires 12/27/20) […]


Maybe I am missing something but how do you actually get to this island and how do you get food while there (except for the one meal they give you)?


Yep. That’s what I was thinking.


Now…that looks boring as anything…but one person’s junk, is another man’s treasure.


I looked at it and thought “that could be fun for a weekend”, but I could not imagine doing 7 nights there. Especially as it does not include boat transfers in that price, so that’s quite a bit more if one doesn’t have a boat.

If the offer was 3 nights for $1000, I could see it being cool, but 7 nights for $2k on the week *before* Thanksgiving (I know, it’s a Friendsgiving promo, but it still isn’t the actual holiday week) seems EXTREMELY boring to me.


We were going to drop more than that on our portion of a family-reunion 26-person house in the Outer Banks of NC in July before COVID-19 cancelled that plan. My wife tells me the schedule for this promo does not work well for 5 virtual schoolers … though I am not sure why given they are all just doing computer-based school anyway. I do have a meeting next week that starts at this time, but I can probably hit refresh a couple times and try to win in the 5 msec it will be available because why not. Buy now, figure it out later.