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Short Term Rentals Jobs in Key West, FL (NOW HIRING)

Better Talent

Revenue Manager

Key West, FL · Remote

$80K - $100K/yr

Required Qualifications * 2+ years minimum of revenue management experience in Short term rentals / vacation rentals * Proven expertise in data analysis and performance monitoring. * Advanced ...

STO Building Group Inc.

Project Manager

Key West, FL · On-site

Manage procurement and approve material purchases, equipment rentals, and jobsite tools not ... Insurance, Short-term Disability insurance, Critical Illness Insurance, Accident Insurance ...

All JobsShort Term Rentals JobsShort Term Rentals Jobs in Key West, FL

Short Term Rentals information

See Key West, FL salary details

$14

$18

$24

How much do short term rentals jobs pay per hour?

As of Jul 28, 2026, the average hourly pay for short term rentals in Key West, FL is $18.96, according to ZipRecruiter salary data. Most workers in this role earn between $16.63 and $20.91 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive in the Short Term Rentals position, and why are they important?

To thrive in Short Term Rentals, you need strong property management skills, attention to detail, and knowledge of local rental regulations, often supported by experience in hospitality or real estate. Familiarity with booking platforms (such as Airbnb or Vrbo), property management software, and customer relationship management tools is typically required. Exceptional interpersonal skills, problem-solving ability, and adaptability help you stand out in this dynamic, guest-focused role. These skills ensure smooth operations, excellent guest experiences, and compliance with industry standards, all of which are key to building a successful short term rental business.

What are the most common challenges faced in a Short Term Rentals role and how are they typically managed?

Professionals in Short Term Rentals frequently encounter challenges such as coordinating quick turnovers between guests, handling last-minute booking adjustments, and addressing maintenance issues efficiently. Managing guest expectations and providing timely responses are also essential to maintaining high ratings and repeat business. Teams often work collaboratively, communicating with cleaning staff, maintenance providers, and guests to ensure seamless operations. Having clear protocols and leveraging property management technology can help streamline communication and keep properties guest-ready. Successfully addressing these challenges leads to higher guest satisfaction and optimizes occupancy rates.

What is a Short Term Rentals job?

A Short Term Rentals job involves managing properties that are rented out for short stays, typically ranging from a few nights to a few months. Responsibilities may include handling bookings, communicating with guests, coordinating cleanings, and ensuring a smooth rental experience. This role can involve working for a property management company or as an independent host. Strong customer service skills and knowledge of local rental regulations are often essential.

What job categories do people searching Short Term Rentals jobs in Key West, FL look for? The top searched job categories for Short Term Rentals jobs in Key West, FL are:
What cities near Key West, FL are hiring for Short Term Rentals jobs? Cities near Key West, FL with the most Short Term Rentals job openings:
Short Term Rentals jobs near you
Revenue Manager

Revenue Manager

Better Talent

Key West, FL • Remote

$80K - $100K/yr

Full-time

Medical, Dental, Vision, Life, PTO

Posted 14 days ago

Job description

Company Overview

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.

From quick weekend getaways to monthly stays, from Key West's historic streets and sunset celebrations to the world-class fishing, diving, and boating of the Upper and Middle Keys, Seven Keys Vacations brings local expertise and professional management to every stay.

Seven Keys Vacations is a proud franchisee of Casago, North America's largest specialized vacation rental manager.

Position Summary

We're looking for a Revenue Manager who thrives on turning data into strategy and strategy into results. In this role, you'll own the revenue performance of multiple short-term rental portfolios, using your analytical expertise and deep platform knowledge to drive measurable growth. You'll be the trusted advisor our PM Partners rely on - someone who doesn't just report numbers, but interprets trends, anticipates market shifts, and translates complexity into clarity. This is a role for a strategic thinker who enjoys solving problems, optimizing systems, and continuously learning in a fast-paced, data-driven environment.

Responsibilities

  • Lead end-to-end revenue strategy and dynamic pricing across diverse short-term rental portfolios.

  • Configure and optimize leading RMS tools (Streamline, KDD, Wheelhouse, RevMax) to drive NOI and long-term performance.

  • Analyze pacing, market data, and booking velocity to anticipate opportunities before competitors react.

  • Deliver monthly performance reviews with clarity, transparency, and insight - translating data into confident business decisions.

  • Continuously refine pricing layers (minimum stays, discounts, fees) aligned with portfolio and market goals.

  • Build enduring, trust-based partnerships through proactive communication and a commitment to measurable impact.

  • Collaborate cross-functionally with data and product teams to refine automation, enhance reporting, and fuel innovation.

  • Challenge assumptions, test new ideas, and adapt strategies to stay ahead of shifting market conditions.

Required Qualifications

  • 2+ years minimum of revenue management experience in Short term rentals / vacation rentals

  • Proven expertise in data analysis and performance monitoring.

  • Advanced proficiency with leading Revenue Management Systems (RMS) such as PriceLabs, Wheelhouse, Beyond, or RevMax.

  • Hands-on experience with Property Management Systems (PMS) such as Guesty, Hostaway, Streamline, or Track (other modern PMS experience is a plus).

  • Proven ability to synthesize complex data into clear, actionable insights.

  • Exceptional relationship management and communication skills; confidence presenting data-backed strategies to executive stakeholders.

  • High personal accountability and attention to detail across multiple portfolios.

  • Deep care for client success and a drive to deliver measurable business results.

  • Self-motivated and organized. Comfortable operating with independence in a remote, results-oriented environment.

Compensation & BenefitsAnnual Salary

$80,000 - $100,000

Bonus

  • Personal and team performance goals

Benefits

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

  • Health, Dental, and Vision insurance

  • Life insurance