Job Specifications
AI-Powered Guest Operations Specialist
Villa Paraiso Vacation Rentals
Remote | Latin America & Philippines Candidates Preferred
Schedule: Friday–Tuesday, 8:00 AM–4:00 PM ET (flexibility for occasional after-hours needs)
Rate: $5–10/hour USD based on experience | Growth Path to Operations Manager
About Villa Paraiso
We're a fast-growing luxury vacation rental company managing 20+ premium waterfront properties across Miami and the Florida Keys. We're not your typical STR company—we're building the future of vacation rental operations using AI automation, smart workflows, and cutting-edge tools. We need someone who can keep up.
The Role
This isn't a "just answer messages" VA position. You'll be the operational backbone of our guest experience, working independently in a fast-paced, tech-driven environment. You'll leverage AI tools daily, troubleshoot systems, and help us improve our automated workflows. If you love solving problems, working autonomously, and staying ahead of the curve in hospitality tech, this is your role.
What You'll Actually Do:
Guest Operations (50%): Respond to guest inquiries across Airbnb, VRBO, Booking.com, and direct channels with speed and hospitality excellence
Systems & Workflow Management (50%): Maintain Guesty PMS, Breezeway task management, Google Sheets, and internal coordination tools
AI-Enhanced Communication: Use ChatGPT, Claude, and other AI tools to draft responses, troubleshoot issues, and optimize workflows
Vendor Coordination: Route maintenance, housekeeping, and service requests to our contractor network
Content Support: Assist with Canva graphics, social media coordination, and marketing materials
Process Improvement: Identify bottlenecks and suggest workflow improvements using our existing AI automation systems
You're a Great Fit If You:
Must-Haves:
1-2+ years in short-term rental operations (vacation rentals, property management, or hospitality)
Guesty PMS experience is non-negotiable (you should know it well)
Fluent Spanish & strong English (slight accent okay, but must communicate clearly)
AI-savvy: Comfortable using ChatGPT, Claude, AI image tools (Kling, Sora, etc.), and learning new tech quickly
Highly independent: You don't need hand-holding. You see what needs to be done and do it.
Available Eastern Time business hours with flexibility for occasional after-hours needs
Big Bonus Points:
Breezeway experience (or similar task management platforms)
Canva and social media content experience
Experience troubleshooting automations or n8n workflows
Natural problem-solver who loves optimizing processes
What We Offer:
Fast-paced, innovation-first culture where your ideas matter
Clear growth path to Operations Manager for top performers
Work with cutting-edge AI tools and help shape our automation strategy
Autonomy & ownership over your work—no micromanagement
Exposure to luxury hospitality in one of the world's best vacation markets
Not a Fit If:
You need constant supervision or detailed instructions
You're uncomfortable with technology or learning new tools
You prefer slow-paced, predictable work
You don't have Guesty experience
To Apply:
Email info@paraisovacationrentals.com with:
Your resume
A short note (3-4 sentences) about your Guesty experience and which AI tools you currently use
Subject line: "AI Operations Specialist - [Your Name]"
We review applications on a rolling basis. Top candidates will be contacted within 48 hours.
About the Company
Villa Paraiso sets the gold standard for vacation rentals in Miami, Florida, and Marathon Florida. From handpicked properties to personalized private concierge services, we go beyond traditional rental experiences to provide unparalleled luxury. Our commitment to quality and elegance ensures a vacation rental tailored to your needs. Villa Paraiso offers a level of sophistication and relaxation that simply can’t be matched elsewhere. We’re not just offering a stay, we’re creating a personalized experience that is a level abov...
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