Waikiki Vacation RentalsVacation Rental Insurance

Vacation Rental Insurance

You've done all the research and planned the perfect vacation getaway to explore the beauty of Waikīkī and Oʻahu, including booking that great vacation rental! You're ready to start packing! But have you given any thought to protecting your investment with trip cancellation insurance?

Protect Your Vacation Investment with Red Sky Sun Trip Preserver!

We understand that vacation travel is invested with hopes and dreams as well as funds. When the unexpected happens, we want you to recover your investment along with the ability to plan again. The optional Red Sky Sun Trip Preserver Travel Insurance is available to all guests of Captain Cook Resorts, whether from the U.S. or international guests. 

Sun Trip Preserver provides you and your traveling companions with valuable benefits before, during, and after your vacation.


  • Trip Cancellation - 100% of Trip Cost
  • Trip Interruption - 100% of Trip Cost
  • Travel Delay - $750 per person ($200 maximum per day)
  • Baggage Delay - $1,000
  • Medical Expense - $25,000 (Primary)
  • Baggage and Personal Effects - $1,250
  • Emergency Medical Evacuation - $525,000
  • Rental Car Damage - $25,000

Travel insurance reimburses for pre-paid, non-refundable expenses due to certain unforeseeable circumstances such as ​​illness, injury, natural disasters, mandatory evacuation, or job loss that may jeopardize your vacation investment and force you to incur unplanned expenses. We strongly recommend you protect your investment by purchasing this valuable protection. For more detailed information please visit: https://www.trippreserver.com/products/sun-trip-preserver/.

For questions about the Sun Trip Preserver Policy, please call Red Sky at 866-889-7409.

If you would like to add the Sun Trip Preserver travel insurance to your reservation, call your Captain Cook Resorts vacation planner at (808) 738-5507.

Coronavirus Questions and Answers

  1. If a traveler tests positive for COVID-19 in their pre-departure CLIA-provided test for the COVID-19 virus and they subsequently share the positive test results with their physician, they ARE entitled to a trip cancellation reimbursement as long as they submit the written test results and an Attending Physician Statement stating the diagnosis of COVID-19 and formal written restrictions against travel.
  2. If a traveler fails a temperature test and is denied boarding their flight due to the temperature test failure they ARE NOT entitled to a trip cancellation reimbursement due to the temperature test failure alone. If a traveler fails a temperature test and is denied boarding their flight due to the temperature test failure they ARE entitled to a trip cancellation reimbursement if subsequent to failing the temperature test they visit a physician and receive a diagnosis of any sickness (including COVID-19). To qualify for a trip cancellation reimbursement in this scenario the insured guest must submit an Attending Physician Statement with a stated diagnosis of a disease (including COVID-19) and a formal written restriction against travel.
  3. Those without travel insurance who test positive for COVID-19 in their pre-departure CLIA-provided test will be responsible for full payment of their reservation (less fees).

To help you better understand the Trip Preserver travel insurance policy benefits, below are some helpful Questions and Answers that may address your concerns prior to your trip. If you need additional guidance, please contact us at 1-866-889-7409.

Please note that these answers only apply to customers whose Policies include the applicable benefits. All other Policy terms, conditions, and exclusions apply.

Q. If I, a traveling companion, or a family member contract the Coronavirus before my trip, am I covered for Trip Cancellation?

A. The following policy language applies to trip cancellations due to a sickness (including COVID-19) occurring after the effective date of coverage:


We will reimburse You, up to the Maximum Benefit Amount shown in the Schedule of Benefits, for the amount of the unused non-refundable prepaid Payments or Deposits for the vacation rental and Travel Arrangements You purchased for Your Trip, when You cancel Your Trip prior to departure for a covered Unforeseen reason; including cancellation or change fees.

Trip Cancellation must be due to one of the following Unforeseen reasons:

  1. Your, a Family Member's, a Traveling Companion's, a Service Animal's, or a Business Partner's or a Traveling Companion's Family Member's covered Sickness or Injury, that:
    1. occurs before departure on Your Trip;
    2. requires Medical Treatment at the time of cancellation; and
    3. as certified by a Physician, results in medical restrictions so disabling as to cause Your Trip to be cancelled;
    *An attending Physician's Statement must be submitted for any Trip Cancellation claim due to sickness (including COVID-19).*

Q. If I, or a traveling companion, contract Coronavirus while traveling does the Policy provide medical coverage?

A. Emergency Medical Treatment benefits may be available under the Policy if the Policyholder contracts the virus while traveling regardless of the date of travel. Additionally, Emergency Medical Evacuation benefits may be available if it is determined that transportation to a higher level of care is necessary as a result of contracting the virus while traveling.

Q. If I, or a traveling companion, have a note from a Doctor advising against travel due to underlying medical conditions that create risk for contracting Coronavirus, am I covered?

A. Being advised against travel by a Doctor because an underlying medical condition may put you at a higher risk for contracting coronavirus alone may not be a covered reason under the Trip Cancellation benefit. You, or a traveling companion, must have a documented sickness (including COVID-19) for which you are receiving medical treatment which prevents you from traveling during your vacation reservation stay dates.

Q. If I, or a traveling companion, want to cancel the vacation travel because of a concern, hesitancy, unwillingness, or fear of traveling due to the coronavirus, am I covered?

A. A concern, hesitancy, unwillingness, or fear of traveling due to the coronavirus is not a covered event under the Trip Cancellation or Trip Interruption benefits.

Q. If a county, state, or local government restricts access to the intended vacation destination to local residents only, am I covered?

A. Government ordered travel restrictions allowing access to local residents only, travel bans prohibiting travel, travel advisories against travel are not covered events under the Trip Cancellation or Trip Interruption benefits. These government ordered restrictions, bans and advisories are not considered to be road closure.

Q. If my, or my traveling companion's, state, or my vacation destination, has implemented a "shelter in place" or a "stay at home" order, is that considered to be a quarantine and am I covered?

A. There are no benefits under the policy for "shelter in place" or "stay at home" orders issued as they are not considered quarantines as defined by the CDC or the Code of Federal Regulations. These orders are intended to prevent further spread of COVID-19 in a community. Unlike quarantines that completely prohibit the movement of individuals, there are many exceptions provided under these orders that permit people to leave their homes for essential activities including (but not limited to) seeing a doctor for medical care, grocery shopping, picking up carry-out from restaurants, and outdoor exercising while practicing social distancing. Furthermore, these circumstances do not require individuals to have been exposed to the virus and therefore required to be quarantined.


*Insurance coverages described above are underwritten by Arch Insurance Company NAIC #11150, under policy series LTP 2013 and endorsements thereto. Policies are administered by Arch Insurance Solutions, 1-855-286-8349, CA License #0118111, TX License #1787195. Your policy is the contract that specifically and fully describes your coverage. Certain restrictions and exclusions apply and coverages may vary in certain states. Please refer to your policy for detailed terms and conditions.*

For more information on COVID-19, please visit the World Health Organization's website at https://www.who.int/emergencies/diseases/novel-coronavirus-2019, or the CDC's website at https://wwwnc.cdc.gov/travel/noticescovid19, or consult your medical professional.