Owner Relations & Admin Coordinator (Remote / Full-Time)

Island Stays Hawaii | Brokered by Halepuna Real Estate Hawaii Compensation: $1,500–$2,000 USD/month (DOE)

About Us

Island Stays Hawaii is a fast-growing short-term and mid-term rental property management company based in Honolulu, managing a portfolio of over 35 properties across Oahu. We're looking for a highly organized, detail-oriented professional to serve as a right hand to our owner/broker — handling administrative operations, owner communications, and light executive assistant support.

About the Role

This is a hybrid Executive Assistant / Admin Coordinator position. You'll be the person keeping our paperwork, payments, and owner relationships running smoothly behind the scenes — and, for many of our property owners, you may be the primary point of contact they interact with day to day. Because of that, excellent, natural, native-level English (written and spoken) is non-negotiable for this role — owners should never feel like they're speaking with anyone other than a core member of our US-based team.

This is currently a generalist role covering several functions at once. As we grow, we plan to bring on more specialized tea ---------- mbers for individual functions (invoicing, leasing, etc.) — but for now, we need one strong all-around operator to close the gap.

Responsibilities

Owner Relations

Serve as a responsive, professional point of contact for property owners via email and phone
Answer owner questions about statements, disbursements, bookings, and property updates
Draft and proofread owner-facing correspondence with zero grammatical or tonal red flags

Property Management & Leasing Documentation

Prepare, send, and track property management agreements (PMAs) and addenda for e-signature
Draft and manage mid-term lease agreements; track lease start/end dates and renewals
Maintain organized, correctly-named document filing in Google Drive (owner name, property, execution status)

Administrative & Invoice Support

Process and code vendor/contractor invoices for payment (see note on approval workflow below — this role enters and prepares payments, it does not have unilateral fund release authority)
Track recurring bills, renewals, licenses, and vendor contracts
Maintain task trackers and follow up on outstanding items across the team

Executive Assistant Support

Manage and triage a portion of the owner/broker's personal email inbox
Assist with scheduling, calendar management, and light research tasks
Requirements
Native or near-native fluency in English, written and spoken — this will be assessed via a live call as part of the interview process
2+ years of experience as a virtual assistant, executive assistant, or administrative coordinator, ideally supporting a US-based client or company
Strong written communication skills; comfortable drafting professional correspondence independently
Highly organized with strong follow-through on multi-step, recurring tasks
Comfortable with Google Workspace (Gmail, Drive, Docs, Sheets); experience with property management or bill-pay software (Guesty, QuickBooks, ---------- , Relay, etc.) is a strong plus
Prior experience in real estate, property management, or hospitality is a plus but not required
High degree of discretion and trustworthiness — this role will have exposure to financial documents and confidential owner information
Must be available to work US Hawaii time zone business hours (HST)
Compensation & Logistics
$1,500–$2,000/month USD, based on experience, paid monthly
Full-time, independent contractor position
100% remote
Growth path: as the team scales, this role may evolve into a more specialized or supervisory position
How to Apply

Please submit:

Your resume/CV
A brief (3–5 sentence) written introduction in English, in your own words, describing your relevant experience
Availability to complete a short recorded video or live call as part of the screening process

We're looking to fill this role quickly for the right candidate — early applicants will be prioritized.