Simply Anini house for rent living room overlooking the grass and oceanSimply Anini house for rent living room overlooking the grass and oceanSimply Anini house for rent living room overlooking the grass and ocean

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a Rental Home

Contact us regarding a villa, listing your villa, or any general inquiry.

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How Do I Book a Rental Home?

1. Contact Hawaii Hideaways

We have hundreds of properties in our inventory, not all are listed online.

Submit an inquiry or call 808-878-5642. You will be connected with the first available agent for immediate assistance. Request to speak with one of our Hawaii Destination Experts and they are happy to answer any questions and research our inventory for properties per your specifications.

Be prepared with your dates of travel, the number of guests in your party, your price range, any specific criteria you may have, and how to reach you.

Email or request to speak with one of the following specialized Hawaii Destination Experts:

2. Plan Your Stay

A Home Coordinator will confirm availability and rates for various properties specific to your party and preferred travel dates. Remember to book early! Almost every month in Hawaii is peak travel season.

What does this mean? There are generally no discounted rates, even for longer stays; demand in Hawaii is high enough that properties can generally be very well booked with shorter reservations at full rates. Starting approximately 2-3 months prior, varying per and by initiative of owner, rates may become discounted for remaining availability or cancellation.

Best availability for Holidays, check 9-12 months prior, generally stays 7-10 days in length can’t occupy both Holidays. Holidays constitute two weeks, one over Christmas the other over New years, December 27th/ 28th usually separates. In an ideal world December 27th/ 28th would always fall on a Sat/Sun. December 25 – January 1 are definitely unacceptable Holiday travel dates for most property owners, as are less than 7 night stays.

Best availability for Winter and Spring, check 6-12 months prior.

Best availability for Summer, check 6-12 months prior. July is the first ‘Summer Break’ month to book, early June and late August/early September the last to book. Always best to book accommodations before purchasing plane tickets!

Inquiries made within 6 months, expect to be asked if you have any flexibility in your requirements, particularly dates of travel and location!

For best last minute, impromptu availability, and lowest rate travel, including potential discounts for longer stays, consider traveling late April, May, late September, October, early November, and early December.

3. Create Your Options

Please provide your Hawaii Hideaways Home Coordinator with the information requested below and you will be sent a link to options that includes photos, a quote for your stay, and any other property information on file.

  • Name
  • Email
  • Telephone number. Let us know a good time to call!
  • Name of each guest in your party and ages of any children
  • Exact or flexible travel dates
  • Exact or flexible location/island
  • Preferences vs Must-Haves. Beachfront, walking distance to restaurants, pool, or other special requirements.
  • Maximum budget range.

Please note that reservations require an HI accommodation tax – 14.42% for Big Island, Maui, and Kauai; 14.96% for Oahu. Fees vary per property and may require a Refundable Security Deposit, nominal Security Deposit Protection Fee, Resort Fee, Cleaning Fees + 4.17% tax. Processing fee may be waived if you elect to pay by e-check. Inquire for exact break down of quotes.

Work with us! Not all our properties are listed online as inventory changes frequently. With more information or feedback regarding requested/recommended properties, we can check for other options.

When inquiring with location-specific property rental representatives or with full-time Hawaii-based staff and management, such as Hawaii Hideaways, rates across the islands are fixed (yes including between properties in our inventory that are also on VRBO or other reputable Hawaii-specific rental sites!).

You can freely utilize our Home Coordinators’ knowledge of the inventory and island areas to best suit your needs. Our Home Coordinators are all present or former long term residents of Hawaii! Hawaii Hideaways Staff has visited/inspected all properties, owners are interviewed, and our Home Coordinators are often given property tours to optimize & relay familiarity with the inventory. A brief professional profile may be requested by the owner, an email address often provides enough information.

4. Finalize Your Reservation

Deposit required and payment date/s may differ per owner. Standard requirement is 50% of payment due immediately to secure the reservation. The remaining 50% due two months prior to arrival. If your arrival date is within two months, 100% of payment and security deposit are due to secure the reservation. You may pay online.

Hawaii Hideaways accepts payment by bank wire or check. Payment may also be made via Credit Card, however there is a 3.5% Processing fee.

5. Cancellation

The cancellation policy is rather firm. Because any payments received are transferred immediately and directly to private property owners, refunds can only be possibly arranged under exceptional circumstances.

If your plans are at all subject to change, we recommend Travel Insurance. You can purchase Travel Insurance at time of booking and have 10 days to cancel, if your stay is not within 60 days. Policies of private property owners differ.

If possible, Hawaii Hideaways always tries to arrange for a rain check for mutually convenient future dates to both the Owner and Guest, but this can not be contractually guaranteed.

6. Arrival

With receipt of final payment, Hawaii Hideaways will send you driving directions to the property. Come your date of arrival, you will drive to the property where a Guest Services Representative may greet you and take you on a property tour. Some properties provide lock boxes for arrival and others there may have a resort office for check-in.

7. Departure

After an amazing Hawaii vacation, most properties allow simply leaving the keys on the counter and heading for the airport. A professional cleaning team will be in the property immediately after. Typically within two weeks of departure, any security deposit is mailed back to you.

8. Contact Hawaii Hideaways

Start all over again and secure your reservation for next year!