Vacation Rental Jobs in Oregon (NOW HIRING)

What we do and why we do it

As the leading end-to-end investment platform for single-family rental homes (SFR), our mission is to reinvent the rental housing ecosystem for the benefit of all. We successfully merge our passion for helping investors build wealth through real estate with cutting edge technology that transforms the way they do it.

How it's going (and growing)

With a talented team of 750+ Roofsters, our collaborative, can-do culture is what fuels our growth. In 2022, we closed on our Series E, raising $240 million, and have offices in the Bay Area and New York City. Our growth includes recent acquisitions of Stessa (financial and asset management software), RentPrep (tenant screening and placement service for landlords), and Mynd (property management platform for both Retail and Institutional investors). In 2025, Roofstock took an ownership stake in Casago (short-term rental management services), expanding our platform to support both long-term and short-term rental investment services.

Roofstock's Values Short-Term Rental (STR) Org Reflection

• We are entrepreneurs Launch a startup within a startup
• We are better together Work across functions & business units to do it fast and well
• We focus on impact Build a profitable business unit with satisfied owners, teammates, and guests
• We think like investors Enhance owners' and Roofstock's ROI

About the Team

Roofstock's STR team has the opportunity to build and shape an entirely new business unit together. The team is obsessed with people, in particular our owners, our guests, and our teammates. We extend our hospitality to everyone around us, there's no such thing as "not my job," and we celebrate our wins together. We plan to expand within our current markets as well as to roll out new markets in the years to come. Much like a startup business, things are fast-paced, intense, and exhilarating. And when the team wins, we all win. 

About the Role

As a Senior Housekeeper, you are the quality gatekeeper and mentor within our housekeeping operation. In addition to performing high-standard cleans, you'll inspect the work of others, train new housekeepers, support consistency across properties, and help resolve urgent in-field issues.

This is a hands-on, field-based role ideal for someone who leads by example, takes pride in cleanliness and presentation, and enjoys coaching others to succeed. 

This part-time seasonal role starting in March and ending in September.

Responsibilities

• Perform full-service turnovers of vacation rental homes per brand standards
• Inspect cleans completed by other housekeepers and ensure adherence to SOPs
• Provide mentorship and on-the-job training to new or developing housekeepers
• Help resolve field issues when urgent issues or concerns arise
• Support spot cleans, touch-ups, or guest service follow-ups as needed
• Ensure homes are functional, clean, and stocked (FCS) prior to guest arrival
• Restock consumables and stage decor, linens, and hospitality touches
• Report damages, maintenance needs, or supply gaps via operational systems
• Provide feedback to management on trends, common issues, or performance gaps
• Provide cross-coverage for your manager when necessary.
• Other duties as assigned

Work Environment
This is a highly physical, field-based role that involves cleaning, lifting, standing, walking, and bending for extended periods. Work will take place inside vacation rental properties as well as outside around driveways, decks, and entryways. The ability to work independently and move quickly between homes is essential

Qualifications

• 2+ years of experience in housekeeping, vacation rental operations, or hospitality
• Demonstrated quality, consistency, and attention to detail in cleaning execution
• Positive attitude and ability to coach and support team members in the field
• Strong understanding of turnover workflows and SOPs
• Physically able to perform cleaning tasks including lifting 25+ lbs, kneeling, and standing for extended periods
• Reliable transportation and valid driver's license
• Smartphone access and comfort using mobile apps to manage tasks
• Availability to work weekends, holidays, and occasional evenings as needed

Location - [Rockaway Beach, OR] (On-site)

Travel Required
Frequent local travel between homes

Compensation

• Piece rate ranging between $35 and $310 per unit
• $24.50/hr per hour paid for non cleaning tasks

Pay Transparency

Our compensation reflects several US geographic markets. The base pay for this position represents the expected salary for this position.  Ultimately, in determining your pay it will be based on several factors including location, job-related knowledge, skills, experience and other job related factors.  Roofstock is a total compensation company; the base salary is only a part of our total compensation package.

Competitive & Unique Benefits Package

• Generous PTO Policy
• 12 Paid Holidays
• Volunteer Time Off
• Paid Parental Leave
• 401k Program
• $35/month cell phone subsidy
• Paid sick time
• Holiday stipend 
• Robust health, dental, vision insurance, and more

Must be authorized to work in the U.S. is a precondition of employment and we are unable to sponsor H1-B Visas at this time.

Any offer of employment is conditioned upon the successful completion of a background investigation. 

Commitment to Equal Employment Opportunity 

The company provides equal opportunity in all of our employment practices to all qualified employees and applicants without regard to race, color, religion, sex, gender, gender expression, gender identity, national origin, ancestry, citizenship, age, physical or mental disability, marital status, sexual orientation, military or veteran status, genetic information or any other category protected by federal, state and local laws. This policy applies to all aspects of the employment relationship, including recruitment, hiring, compensation, promotion, transfer, disciplinary action, layoff, return from layoff, training and social, and recreational programs. All such employment decisions will be made without unlawfully discriminating on any prohibited basis.