Vacation Rentals Guest Operations Specialist

AI-Powered Guest Operations Specialist
Villa Paraiso Vacation Rentals
Remote | Latin America & Philippines Candidates Preferred
Schedule: Friday–Tuesday, 10:00 AM–5:00 PM ET
Rate: $5–10/hour USD based on experience | Growth Path to Operations Manager

About Villa Paraiso
We're a luxury vacation rental company managing 20+ premium waterfront properties across Miami and the Florida Keys. We operate with an AI-forward mindset—leveraging automation, smart workflows, and cutting-edge tools to deliver exceptional guest experiences at scale. We need someone who thrives in that environment.

The Role
This isn't a "just answer messages" position. You'll be the operational backbone of our guest experience—working independently, solving problems in real-time, and keeping our properties running smoothly. You'll use AI tools daily, manage multiple systems, and help us continuously improve how we operate.

A Typical Shift Might Include
Responding to 20-30 guest messages across platforms
Coordinating 3 check-ins and 2 check-outs with the cleaning team
Troubleshooting a WiFi issue with a guest
Updating a reservation in Guesty after a date change
Flagging a maintenance issue in Breezeway
Drafting an owner update email using Gemini

What You'll Do
Guest Operations (60%)
Respond to guest inquiries across Airbnb, VRBO, ---------- , and direct channels with speed and professionalism
Handle check-in/check-out coordination, guest requests, and issue resolution
Manage reservation modifications, cancellations, and special requests in Guesty
Monitor and respond to guest reviews

Systems & Workflow Management (25%)
Maintain Guesty PMS—reservations, listings, messaging, and reporting
Coordinate tasks in Breezeway for housekeeping, inspections, and maintenance
Keep Google Sheets, trackers, and internal documentation updated and accurate
Flag system issues and help troubleshoot when automations break

AI-Enhanced Operations (15%)
Use ChatGPT, Claude, and AI tools to draft responses, solve problems, and work faster
Learn and adapt to new tools quickly as we evolve our tech stack
Identify opportunities to automate repetitive tasks

Vendor & Team Coordination
Route maintenance requests, housekeeping issues, and service calls to our contractor network
Communicate with field team on property needs and urgent situations
Track open issues to completion



Must-Haves:
1-2+ years in short-term rental operations (vacation rentals, property management, or hospitality)
Guesty PMS experience—non-negotiable (you should know it inside and out)
Fluent Spanish and strong English communication skills
Comfortable using AI tools (ChatGPT, Claude) and learning new technology quickly
Highly independent—you see what needs to be done and handle it without being asked
Reliable internet and professional remote work setup

Strong Bonus Points:
Breezeway experience (or similar task management platforms)
Familiar with HostBuddy, StayFi, or other STR tools
Experience with automation platforms (n8n, Zapier, Make)
Background in hospitality or customer service excellence

What We Offer
Growth Path: Top performers can advance to Operations Manager within 12-18 months, taking on team oversight, owner communications, and strategic projects. We promote from within.
Work with cutting-edge AI tools and help shape our automation strategy
Autonomy and ownership—no micromanagement, just accountability
Fast-paced environment where your problem-solving skills actually matter
Exposure to luxury hospitality in Miami and the Florida Keys

About After-Hours: After-hours needs are rare (1-2x/month) and typically involve urgent guest issues like lockouts or emergencies. We don't expect you to be on-call 24/7—we have systems for that.

Onboarding: You'll get structured training covering our systems, SOPs, and properties before handling guest communications independently.

Not a Fit If
You need constant supervision or step-by-step instructions
You're uncomfortable with technology or resistant to learning new tools
You prefer slow-paced, predictable work
You don't have hands-on Guesty experience

Prescreening Questions
Please answer ALL of the following in your application:

Guesty Knowledge Test
In Guesty, how would you set up an automated message to send check-in instructions 3 days before arrival, but ONLY if the guest has completed their check-in form? Walk me through the specific steps and settings you would use.

Review Response Challenge
A guest leaves a 3-star review saying: "The place was nice but communication was slow and we never got our pool heated." You know the guest never requested pool heat and you responded to all their messages within 15 minutes. Write the actual public response you would post.

AI Skills Demonstration
Using ChatGPT or Claude, draft a response to this guest message:

"Hi, we're arriving Thursday but our flight got moved to 11am arrival. Can we check in early? Also is there a Publix nearby and can we bring our kayak?"
Paste three things: (1) your prompt to the AI, (2) the AI's output, and (3) your final edited version you would actually send to the guest.

Prioritization Scenario
Begin your answer with the words "Here's my approach:" — It's Saturday at 2 PM. You have four things hitting you at once:
A guest is locked out in Key Colony Beach
A cleaning team is asking if the Unit 7 checkout was extended
An owner is emailing about their June statement
A new VRBO inquiry is asking about boat dock depth
Rank these in the order you'd handle them and explain why.

Policy Enforcement
A guest messages you: "Can we have 12 people over for my husband's birthday dinner on Saturday? We'll be quiet, I promise." The property's maximum occupancy is 8. Write your actual response to the guest.

Emergency Response
A guest messages at 7 PM saying their AC isn't working and it's 85 degrees inside. Walk me through exactly what you would do, step by step.

Automation Thinking
What's one repetitive task in vacation rental operations that you think could be automated but usually isn't? How would you automate it?

Self-Awareness
Be honest: What's something about this job description that concerns you or that you'd want to know more about before accepting?

Technical Requirements
What is your internet speed? Please run a test at ---------- and include a screenshot of your results. Do you have a backup internet option if your primary goes down?

Availability Confirmation
Confirm: Are you available to work Friday through Tuesday, 10:00 AM to 5:00 PM Eastern Time?

To Apply
Send your resume and complete answers to ALL prescreening questions above.
Important: Include the phrase "Keys Ready" as the first words in the subject line of your application email so we know you read the full posting.
We review applications on a rolling basis. Top candidates will be contacted within 48 hours.