Brian B.
Poor at ever step of the way
Poor at ever step of the way. I expected better.

Arch Red Sky Insurance offers travel insurance for the vacation rental industry, providing coverage for coastal, lake, ski and mountain destinations.
Arch Red Sky Insurance (redskyinsurance.com) has 424 customer reviews on Five Star Index, with an average rating of 3.9 out of 5.
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Brian B.
Poor at ever step of the way. I expected better.
Blake
I filed a claim because I ended up having to cancel a family trip to Destin, FL last week due to Hurricane Isaias. This company only reimbursed me for 2 days of the trip because the city had lifted the mandatory evacuation order on the 3rd day. So despite most of the city being without power, most of the restaurants and businesses closed, and all of the locals scrambling to piece their lives back together, Red Sky apparently thinks I should've checked in anyway! Even if I'd wanted to check in on this date, however, I wouldn't have been able to because a flights were no longer available. This is nothing more than a scam. The soulless agent I spoke to on the phone didn't make matters any better. Hope these people all have the day they deserve.
Len T.
We haven’t received our refund checks. It’s been 23 days since we were told they were mailed
Ashley T.
I paid almost $700 for a trip that a personal family emergency caused me to cancel, and they refused to give me even a partial refund because I didnt have 100 pages of documentation. What's the point of having travel insurance, if you're still gonna lose the money? Save yourself some trouble and don't use them.
Response from Arch Red Sky InsuranceOct 7, 2026
Ashley, Thank you for reaching out to us. As with any insurance claim, in order to adjudicate a claim in accordance with the terms of the policy, whether to approve or deny, our examiners require complete documentation supporting such claim. In reviewing the communications on your claim, we asked for details about the cancellation and they were not provided. If you have any documentation to support your claim, we would be happy to reevaluate. We appreciated your patience as we evaluated your claim. At the time of posting, we understand that your issue has been resolved. Regards, The Arch Red Sky Team
John L.
The amount paid is not the correct amount you said code 133 indurance coverage not refundable but you already took it out in your calculation showing 1412 should be paid.
Response from Arch Red Sky InsuranceSep 1, 2026
John, Thank you for reaching out to us. At the time of posting, we understand that your issue has been resloved. Regards, The Arch Red Sky Team
Michael P.
Do not ever buy this insurance; you have to be dead, and prove it four different ways before any analyst will consider returning your money. Can't imagine doing business like this. Put a 7K deposit down and only get 3K back because the reason for cancellation doesn't qualify. It is theft at its finest.
Response from Arch Red Sky InsuranceJul 16, 2026
Michael, Thank you for reaching out to us. Travel insurance is a named peril insurance, meaning only covered events outlined in your policy are insured. Since your circumstance did not meet a covered reason under your policy, your claim was considered under the CancelFlex benefit which you purchased with the insurance. The claim was paid at the maximum amount under the CancelFlex benefit. We understand you are disappointed with the outcome, however, we are required to adjudicate claims according to the terms of your policy. If you have any further questions you can contact us at 866-889-7409. Regards, The Arch Red Sky Team
Terri S.
We purchased a travel insurance policy from Red Sky for a condo rental in the Outer Banks. Unfortunately my husband was deemed medically unable to travel, and we notified the condo rental of our need to cancel on April 16th and filed the necessary paperwork (including Physician Statement) with Red Sky promptly (April 20th). Instead of simply paying this very straightforward claim immediately in good faith, they instead sent repeated faxes to the doctor to re-ask the same questions that were answered on the Physician Statement. If you look at BBB or Yelp, you will note this is not an uncommon tactic for them to delay or avoid claim payment. Doctors don't have time to re-answer the same questions. I had to get their corporate counsel involved to then have them miraculously find some coverage. Even then, they did not pay the entire rental cost, even after several emails pointing out this fact. Instead of double checking with the condo rental company to verify the full cost, they just ignored me. The vacation rental company did reimburse this final cost which should have been paid by Red Sky. Take a tip. Call Tin Leg or some other insurer, but avoid this one.
Response from Arch Red Sky InsuranceJul 16, 2026
Terri, Thank you for reaching out to us. As with any insurance claim, in order to adjudicate a claim in accordance with the terms of the policy, whether to approve or deny, our examiners require complete documentation supporting such claim. In this case, we required additional information from the doctor that was not originally provided. Once that information was provided, we were able to process your claim. After reviewing the communications on your claim, we regret that the level of service you received is not indicative of our usual service and the high standards that we strive to meet for all of our travelers. The discrepancy in trip cost should have been explained to you clearer. We appreciated your patience as we evaulated your claim. At the time of posting, we understand that your issue is being or has been resolved. Regards, The Arch Red Sky Team
Jamie
Can I give no stars? I booked a spring break trip to ski at Keystone Mountain in Keystone Colorado. We rented a condo through Summit County Mountain Retreats in the River Run village, as we would not have a car and we could walk to the gondola and restaurants in the mountain village. We did also purchase the travel insurance because spring skiing can easily be cancelled due to weather warming. This year, of course Keystone Mountain and many others closed early 04/05/26. They would be closing two days before we arrived on 04/07/26. So, we weigh our options and call places in the village to see if anything would still be open, all told me they would be closed the day after the mountain closes. So we decide to cancel and file the insurance claim...fast forward they deny my claim stating the resort was accessible. (WHAT?) Mind you, we would have no car, the mountain is closed, the mountain village is closed, but yet I should still be able to go and enjoy my trip?! What the actual F are they thinking???? DO NOT WASTE YOUR MONEY!!!! And when I called to speak to a rep, they blamed the resort and stated they were the ones who told Red Sky it was open and accessible even though I provided proof of the resort closure.
Response from Arch Red Sky InsuranceApr 30, 2026
Jamie, Thank you for reaching out. Your appeal is currently under review. We appreciate your patience during this process and we look forward to providing further assistance with this matter. Regards, The Arch Red Sky Team