Short-term Rental Home Inspector (1099)

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.

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.

Location: Largo, Indian Rocks Beach
Type: Independent Contractor

Seeking independent contractors to support short-term rental homes with inspections, light prep, and in-market assistance between guest stays.

• Pre/post-stay inspections
• Light home resets and restocking
• Minor maintenance tasks
• Turnover support and trash removal
• Responding to urgent on-site issues
• Task updates via mobile app

• Experience in hospitality, vacation rentals, or property care
• Reliable vehicle and smartphone
• Able to work independently and manage availability
• Comfortable with light physical work
• Weekend availability preferred

• 1099 independent contractor (not employment or benefits eligible)
• Flexible, task-based work
• Contractor responsible for taxes and insurance

Compensation: $19/hour, with the option for per-task/piece-work pay for experienced contractors. We are open to discussing a flat rate per inspection/job.