Live In Direct Support Professional Jobs in Key West, FL

Seven Keys Vacations is a locally led vacation rental management company serving the Florida Keys, with offices in Key West and Marathon and homes throughout Key West, Key Largo, Islamorada, Marathon, Big Pine Key, and the Lower Keys. Our portfolio includes oceanfront homes, canal-front retreats, condos, pet-friendly rentals, and properties with private pools and boat docks — giving owners and guests a wide range of high-quality options across one of Florida's most iconic coastal destinations.

We are led by a team with decades of combined experience investing in, growing, and operating successful vacation rental management companies. That experience is paired with on-the-ground local managers who live in the markets they serve and have the authority to make decisions in real time. We believe vacation rental management is fundamentally a relationship business, and relationships are built locally.

For homeowners, we are an advocate first — focused on protecting the home, maximizing income, and delivering transparent, real-time reporting. For guests, we deliver professionally cleaned, fully equipped homes backed by reliable local support from check-in to check-out, helping make every Florida Keys vacation simple, friendly, and stress-free.

We're looking for a Director of Marketing to lead and scale marketing rental performance across a growing, multi-market portfolio.

This is a high-impact, hands-on leadership role responsible for driving results across return on marketing spending and revenue performance. You will partner directly with ownership and General Managers to bring structure, accountability, and consistency to the rentals function - while ensuring teams are aligned, supported, and performing at a high level.

Success in this role requires someone who moves quickly, takes initiative, and thrives in a fast-paced, evolving environment. You will be responsible for building and refining systems that improve efficiency, elevate the marketing analytics, and enable the organization to scale with confidence.

You’ll operate across multiple coastal markets, stepping in where needed to solve problems, remove friction, and keep operations moving forward. This role is ideal for a leader who combines strong relationship instincts with operational discipline, and who takes pride in turning complexity into clarity.

You'll be the driving force behind our brand presence, orchestrating integrated marketing campaigns across multiple channels while maintaining strong relationships with local partners and guest communities. From crafting compelling content and managing our digital footprint to analyzing performance metrics and optimizing our vacation rental listings, you'll have the opportunity to make a significant impact on our growth and guest experience. This dynamic position offers the perfect blend of strategic thinking and hands-on execution, where your enthusiasm for storytelling and data-driven decision-making will help Seven Keys Vacations to stand out in the competitive vacation rental market.

Digital Marketing & Advertising

• Manage Meta advertising campaigns from setup through optimization

• Meet monthly with ICND account representatives to evaluate advertising opportunities

• Track campaign performance, website traffic, and booking metrics

• Develop audience targeting and re-marketing campaigns to drive bookings and guest retention

• Create segmented guest groups for email re-marketing campaigns

Website, SEO & Analytics

• Work with ICND on website updates, enhancements, and issue resolution

• Create and launch new webpages

• Manage website popups and lead generation tools

• Update featured units on a bi-monthly basis

• Create and publish blog content

• Remove spam comments and maintain website quality

• Regularly monitor Google Analytics (GA4) and website performance metrics

Email Marketing & Guest Communications

• Create and send guest email campaigns through Mailchimp

• Create and distribute owner communications and newsletters

• Maintain accurate guest and owner contact databases

• Transfer new Streamline contacts into Mailchimp guest lists

• Develop and manage guest re-marketing campaigns

• Manage Streamline email templates, including:

  • Creating new templates

  • Modifying existing templates

Social Media & Community Engagement

• Create and manage content for Facebook and Instagram

• Respond to guest messages, comments, and inquiries

• Engage with relevant community groups and special interest audiences to generate awareness and leads

• Monitor social media performance and audience engagement

Content Creation & Brand Management

• Create graphics for social media and email campaigns

• Design guest-facing materials including:

  • Welcome sheets

  • Property signage

• Create graphics for special projects such as:

  • Owner acquisition mailers

  • Owner gifts

  • Employee email signatures

  • Business cards

• Utilize ChatGPT and AI tools to support content creation and brand visibility

• Edit walkthrough videos for use on the website, social media platforms, and YouTube

Listing Management, Reputation & Tourism Partnerships

• Create content for new property listings

• Optimize listing descriptions and headlines across distribution channels

• Upload and manage listing photography in Streamline

• Create SEO-rich photo captions

• Tag photos appropriately for OTA distribution

• Update and maintain Booking.com photos and content

• Refresh and reorder listing photo galleries as needed

• Set up and manage listings on non-integrated platforms such as Furnished Finder

• Coordinate participation in visitor bureau marketing opportunities

• Respond to Google reviews and maintain Google Business Profile content and photos

• Build and maintain relationships with local visitor bureaus and community organizations

• Minimum 2+ years vacation rental marketing experience, website management, and social media experience

• Live in FL Keys within driving distance of either Marathon or Key West office locations

• Know how to make data driven decisions and create data driven metrics to measure success. Know the data tools to use for vacation rental marketing

• Efficient in all things tech, quick learner with new software

• Proven multi-task, organizational skills

• Brand awareness in all things

• Understand "Integrated Marketing" and be able to implement this strategy throughout Florida Keys

$55,000 - $85,000

• Based on company and individual performance goals

• Paid time off such as PTO, sick days, and vacation days

• Health, Dental, and Vision insurance

• Life insurance

• Opportunity for advancement and growth in your role and the company