Our Story

Vacation Doorways has been a family-owned business since its start in 1997 and has grown to be the largest vacation rental agency in the San Juan County. It is also the only one providing luxury vacation rental homes on San Juan, Orcas, and Lopez Islands. With over 80 homes under management and the latest in vacation rental management software and systems, plus an outstanding team of staff members, we are dedicated to our guests and our owners. 

Why Vacation Doorways?

There are many reasons we believe you should consider us for your vacation rental management needs but in the end we decided to let some of our current owners speak for us instead:

Rob – "Vacation doorways has been managing our cabin for the past year. We appreciate their readiness and communication with us over any matter with our cabin. Vacation Doorways staff has been pleasant and prompt with any questions or concerns that have occurred. Thank you for caring and appreciating our little cabin!"


Keith – "San Juan Vacation Doorways provided clear communications throughout the rental permitting process, as well as during the actual vacation rental year. They have been responsive to occasional concerns (barbecue grill, key lock-box, etc.) that have arisen for rental customers, resolving them quickly. Finding just the right pricing model for each weather and holiday season is a challenge, and Vacation Doorways continues to explore different solutions to improve overall rental revenue."


Janice – "Some people manage their own homes for rental, but I cant imagine trying to do everything Vacation Doorways does - and do it well! The whole Vacation Doorways team has been great to work with, professional and organized."

Vacation Rental Home Management

A vacation home. It can be your escape from the demands of employment and routine commitments, a place to reconnect with friends and family. It can be a needed change of pace, refuge, or retirement location in addition to a great real estate investment. But, by definition, a second home tends to be unoccupied much of the time. Short-term rentals can minimize the ongoing expense of vacation home ownership.

Vacation Doorways is the largest and most experienced rental management company in the San Juan Islands. Since beginning as Windermere Real Estate in 1997, we've welcomed thousands of visitors to our beautiful corner of the world; we currently have a marketing database of more than 12,000 former and prospective renters.

We offer a comprehensive range of services designed to eliminate the costly and time-consuming challenges inherent in the “by owner” approach.

Marketing & Management Services:

  • Internet Exposure on Multiple Websites
  • Photography & Descriptions
  • On-line Booking 24/7
  • Brochures, Newsletters
  • Office Staff, Managers, Reservationists
  • Standard Policies for your Protection
  • Guest Confirmations
  • Rate and Amenity Recommendations
  • Credit Card Processing
  • Travel Insurance
  • Payment Collection
  • Integrated Booking Calendar
  • 24/7 Guest Emergency Response.
  • Key Control
  • Housekeeping Staff
  • Guest Information Manuals
  • Home Reviews and Ratings
  • Deep Cleaning Services
  • Winterizing
  • Minor Repairs
  • Real Estate Agency for Buyers & Sellers.
Please call or email Vacation Doorways for more information.

Vacation Doorways PO Box 488 Friday Harbor, WA 98250 +1 (800) 391-8190 vacationrentals@windermere.com

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