Red Sky Travel Insurance’s success combines the broadest most complete protection for your vacationing guests, an A+ rated underwriter (Arch Insurance Company), “high touch” personal service, an intimate knowledge of the vacation rental business, and talented people with a passion for developing long term relationships with our Vacation Rental Management Company partners.

Sun Realty Village Realty BHI


“It has been a pleasure to work with Red Sky as our travel insurance provider since January of this year. The transition process was very smooth. We had many questions and the sales team was very patient and informative while communicating the information we needed to make our transition. We have been very pleased with the claims team who work hard to insure our guests are reimbursed in a timely manner. We would highly recommend Red Sky.”

-Resort Vacation Properties

"Red Sky Travel Insurance provided the most complete coverage available for our guests during the worst events from Hurricane Irene. Their ‘high touch’ personal service is the best!"

-Billy Casper
Vice President, Property Management
Corolla Classic Vacations

“Snowmass Hospitality has been exclusively recommending Red Sky Insurance to our guests with fantastic results. Our guests stay with us because they know we’ll deliver the perfect ski vacation experience, and Red Sky gives them total peace of mind should something unexpected occur. Their focus on the ski industry has made all the difference to us and our guests.”

-Andrew Vick
Snowmass Hospitality

“Red Sky is awesome!!!!!!!!!!!!!!!!!”

-Norman Bibeau
Elan Vacations

“Vacation Rental Pros is very pleased with the quality of customer service and training Red Sky provides. I sincerely appreciate your company's responsiveness and the professional manner in which you conduct claims with our customers. Since my staff is on a bonus for selling insurance, they really appreciate Nancy's quarterly visits to help them better understand the benefits of Trip Insurance for our customers. I have recommended Red Sky to others because of my satisfaction with your service. We look forward to doing business with you for years to come.”

-Steve Milo
Vacation Rental Pros

“Travel plans change and when they do, Red Sky is there to offer peace of mind every step of the way. They offer a friendly, knowledgeable staff that is on hand to assist our guests when a planned trip becomes interrupted. Red Sky gives our guests time to worry about the ‘more important’ things in life, while they take care of the rest.”

-Hilton Head Rentals & Golf

“My family was recently obliged to cancel our reservation for a rental property on Ocracoke Island in the Outer Banks. It’s our tradition to spend a week over the 4th of July there each year, and we’ve come to love the island and its laid back lifestyle.

Unfortunately, my father-in-law Tony was diagnosed with stomach cancer shortly before we were scheduled to go this year, and his care became our top priority. I regret to say that we lost him soon after the diagnosis on July 15th.

Needless to say, we had many difficult issues to deal with, but thanks to you, canceling our reservation and filing our claim with Red Sky to recover our rental costs was easy and painless. We were pleasantly surprised at how quickly you processed it. That was one of the few things that have gone well for us lately.

My family thanks you and your company for your efficiency and promptness. I have often had second thoughts on whether we need to buy trip insurance every year. No longer. I now see how much it is needed, and with your company we can depend on prompt claim resolution.”

-From a Guest of Ocracoke Island Realty

“In my 25 years in the Vacation Rental Industry I have worked with all of the top trip interruption insurance firms. Red Sky is without a doubt the best I’ve worked with. Not even close. ”

-Tim Cafferty GRI, ARM, President
Outer Banks Blue Realty Services

“We believe that training is the most important factor in a successful relationship with our travel insurance provider, and Red Sky is proactive in this area: from regular on-site visits to consistent communications, it’s covered.

Our guests want two things: to understand their coverage and if necessary, fast responses to claims. Red Sky’s online processing keeps guests happy and the entire claim process efficient and transparent.

Red Sky brings the best of both worlds to Sand `N Sea Properties: a focus on our business needs as well as the needs of our guests. ”

-Claire Reiswerg,
Sand 'N Sea Properties