Vacation Rental Guest Operations Specialist
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 are a fast-growing luxury vacation rental company managing 20+ premium waterfront properties across Miami and the Florida Keys. We are not a traditional short-term rental company; we are 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 is not a typical “just answer messages” VA position. You will be the operational backbone of our guest experience, working independently in a fast-paced, tech-driven environment. You will leverage AI tools daily, troubleshoot systems, and help improve automated workflows. If you love solving problems, working autonomously, and staying ahead in hospitality tech, this is the role for you. Responsibilities: • Guest Operations (50%): Respond to guest inquiries across bolthires, VRBO, Booking.com, and direct channels quickly and with hospitality excellence. • Systems & Workflow Management (50%): Maintain Guesty PMS, Breezeway task management, bolthires 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 AI automation systems. Requirements: • 1–2 years of experience in short-term rental operations, property management, or hospitality. • Guesty PMS experience is required. • Fluent Spanish and strong English communication. • AI-savvy: Comfortable using ChatGPT, Claude, AI image tools, and learning new tech quickly. • Highly independent and proactive. • Available Eastern Time business hours with flexibility for occasional after-hours needs. Bonus Points: • Experience with Breezeway or similar task management platforms. • Canva and social media content experience. • Experience troubleshooting automations or n8n workflows. • Strong analytical and problem-solving mindset. What We Offer: • Fast-paced, innovation-first culture where your ideas matter. • Clear growth path to Operations Manager. • Work with cutting-edge AI tools and shape our automation strategy. • Autonomy and ownership—no micromanagement. • Exposure to luxury hospitality in one of the world’s top 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 lack Guesty experience. We review applications on a rolling basis and will contact top candidates within 48 hours. Location: Remote - Anywhere Skills required for this job: • Automated hospitality operations • Breezeway • Canva • ChatGPT • Claude • Guest experience • Guesty • Process improvement Apply tot his job Apply tot his job