Owner Success Manager

SeaBreeze Vacation | Holmes Beach, FL

$50,000–$60,000 Annually | Full-Time | On-Site

SeaBreeze Vacation is a leading vacation rental management company on beautiful Anna Maria Island, specializing in beachfront homes, coastal cottages, and upscale condos. We pride ourselves on delivering exceptional hospitality, maintaining beautiful properties, and building lasting relationships with the homeowners who trust us with their investments.

Our team values communication, accountability, collaboration, and attention to detail. We're looking for someone who shares those values and takes pride in delivering an exceptional homeowner experience.

SeaBreeze Vacation is seeking an experienced, relationship-driven Owner Success Manager to join our team in Holmes Beach, FL.

In this role, you'll serve as the primary point of contact for our homeowners, building trusted relationships, coordinating property maintenance and improvements, and ensuring new properties are successfully onboarded into our rental program. You'll collaborate closely with our Operations, Maintenance, Housekeeping, and Reservations teams to resolve concerns, maintain property standards, and deliver a seamless homeowner experience.

The ideal candidate is a proactive problem-solver who understands the importance of protecting homeowner investments, managing expectations, and following through on commitments. If you thrive in a fast-paced hospitality environment and enjoy balancing relationship management with property operations, we'd love to meet you.

Homeowner Relations & Retention

• Serve as the primary point of contact for homeowners, building trusted, long-term relationships.

• Proactively communicate property updates, maintenance needs, guest feedback, and operational concerns.

• Address homeowner questions and concerns professionally, ensuring timely resolution and follow-through.

• Identify opportunities to improve homeowner satisfaction, property performance, and long-term retention.

• Maintain accurate records of homeowner communications, requests, and outstanding action items.

Property Oversight & Coordination

• Collaborate with Operations, Maintenance, Housekeeping, and Reservations to maintain property standards and resolve issues.

• Coordinate maintenance requests, repairs, vendor services, and homeowner approvals.

• Monitor property inspections, work orders, and follow-up activities to ensure timely completion.

• Provide homeowners with clear property updates and recommendations for preventative maintenance or improvements.

• Identify and address recurring property concerns before they impact homeowner or guest satisfaction.

New Property Onboarding

• Coordinate the onboarding of new vacation rental properties from initial setup through rental readiness.

• Work across departments to ensure inspections, maintenance, housekeeping, inventory, amenities, and photography are completed.

• Communicate onboarding progress, timelines, and outstanding requirements to homeowners.

• Ensure each property meets SeaBreeze Vacation standards before entering the rental program.

Issue Resolution & Accountability

• Take ownership of homeowner concerns, coordinating solutions across internal teams and external vendors.

• Manage multiple requests and priorities while maintaining clear communication and accurate documentation.

• Anticipate challenges, recommend solutions, and ensure commitments are completed on time.

• Minimum of 2 years of experience in vacation rental management, property management, homeowner relations, or hospitality operations.

• Proven ability to build and maintain strong client or homeowner relationships.

• Excellent written and verbal communication skills, including the ability to navigate sensitive conversations professionally.

• Strong organizational skills with the ability to manage multiple properties, requests, and competing priorities.

• Demonstrated problem-solving skills, sound judgment, and a proactive approach to resolving concerns.

• Comfortable coordinating with multiple departments, vendors, and service providers.

• Proficiency with computers, email, and business software.

• Ability to work on-site in Holmes Beach, FL, Monday through Friday, 9 AM–5 PM.

• Previous experience working directly with vacation rental homeowners or property owners.

• Familiarity with property inspections, maintenance coordination, and new property onboarding.

• Experience using property management software, Breezeway, or similar systems.

• You understand that strong homeowner relationships are built on trust, transparency, and consistent follow-through.

• You're comfortable taking ownership of challenges and seeing solutions through to completion.

• You can balance homeowner expectations with operational priorities.

• You're highly organized, detail-oriented, and proactive.

• You communicate confidently, remain calm under pressure, and enjoy collaborating with others.

• You take pride in protecting properties and delivering exceptional service.

$50,000–$60,000, depending on experience.

• Potential annual performance-based incentive/bonus.

• Paid time off, including PTO, sick days, and vacation days

• Health, dental, and vision insurance

• Workplace perks such as recreation activities, food and coffee, and flexible work schedules

• Employee recognition programs

• Gym memberships or discounts

• Monday through Friday, 9 AM–5 PM

• Full-time, on-site in Holmes Beach, FL

If you're passionate about building homeowner relationships, solving problems, and ensuring vacation rental properties receive exceptional care, we'd love to hear from you. Join a collaborative team dedicated to delivering outstanding service to homeowners and guests across Anna Maria Island.