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RedSky

Travel insurance provider for vacation rental management companies offering property protection products.

4.67
15 reviews
Insurance
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About RedSky

Arch Red Sky is a specialized travel insurance provider catering solely to professionally managed vacation rental management companies. Since 2008, Red Sky and Arch Insurance Company have insured guests' vacations in hurricane-prone coastal and snow-dependent ski destinations. Their Trip Preserver products help vacation rental managers and guests protect non-refundable deposits when unforeseen events disrupt vacation plans. Arch Red Sky provides high-touch service, support, and on-site training to VRM companies.

What sets this company apart

Red Sky is one of the few insurance providers exclusively focused on the vacation rental management industry, with destination-specific products for coastal and ski markets, high-touch personalized service, and on-site training for VRM companies. Their products are underwritten by Arch Insurance Company (NAIC #11150).

Markets & Coverage

Operating across 3 countries

Markets & Coverage

(3)
United StatesCanadaMexico

Supported Languages

EnglishPrimary

Market Segments

  • Beach & CoastalPrimary
  • Mountain & Ski
  • Family

Service Characteristics

Main Features

  • White-label option
  • Dedicated account manager
  • Host training programme
  • Claims management portal
  • Travel insurance for guests

Integrations & Partnerships

3 integrations and partnerships across 2 categories

Property Management Systems

2

Channel Managers

1

Reviews

15 reviews from verified users

4.67

15 reviews

87%

Would recommend

Showing 6 of 15 reviews

D

Debby

May 2026
Trustpilot
5

Filing an insurance claim is a dreaded…

Filing an insurance claim is a dreaded event BUT.....became a great experience with how respectful and helpful Cory was! Thank you!

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C

Claudia Caves

May 2026
Trustpilot
5

My claim was answered promptly

My claim was answered promptly, and as soon as I sent in the required paperwork, the claim was accepted. Our check arrived within the number of days we were told it would take. Thank you!

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S

Shirley M

May 2026
Trustpilot
5

Incredible service

I ended up in the hospital and my family could not enjoy our trip to Maui. Red sky went above and beyond expediting our trip insurance and following through with a complete refund. I would recommend red sky insurance to absolutely everyone. Thank you for taking care of us.

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M

Mike B

May 2026
Trustpilot
5

I was pleasantly surprised

I was pleasantly surprised that I got my claim approved without having to jump though a bunch of hoops. My experience was positive!

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D

Debra R

May 2026
Trustpilot
5

I received a full refund on my rental

I received a full refund on my rental. We were just 4 hours from our unit to start our week vacation, when we received a call that my dad pasted away unexpectedly. So glad I took the insurance!! After my claim was made, I received my refund in a timely manner. I would highly recommend taking the insurance.

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J

Jon M

May 2026
Trustpilot
5

Having dealt with insurance before we…

Having dealt with insurance before we were surprised at the short time it took to settle compensation. In past claims (other companies) it took months and many hoops to jump through. Good job, thanks, jon

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FAQ

Frequently Asked Questions

  • Arch Red Sky is a specialized travel insurance provider catering solely to professionally managed vacation rental management companies. Since 2008, Red Sky and Arch Insurance Company have insured guests' vacations in hurricane-prone coastal and snow-dependent ski destinations. Their Trip Preserver products help vacation rental managers and guests protect non-refundable deposits when unforeseen events disrupt vacation plans. Arch Red Sky provides high-touch service, support, and on-site training to VRM companies.

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