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Vacation Rentals Jobs in Florida (NOW HIRING)

Luxury Coastal Vacations

Inspector

Pensacola, FL · On-site

$16 - $17/hr

Luxury Coastal Vacations is a local rental management company that provides premium management solutions for owners, top-notch vacation rentals for guests, and exciting career opportunities for ...

Luxury Coastal Vacations

Inspector

Pensacola, FL · On-site

$16 - $17/hr

Luxury Coastal Vacations is a local rental management company that provides premium management solutions for owners, top-notch vacation rentals for guests, and exciting career opportunities for ...

Career Search

Inspector

Pensacola, FL

Luxury Coastal Vacations is a local rental management company that provides premium management solutions for owners, top-notch vacation rentals for guests, and exciting career opportunities for ...

Better Talent

Inspector

Saint Petersburg, FL

$17 - $19/hr

Company Overview Resort Rentals is a vastly growing vacation rental, property management, and Real Estate company St. Pete Beach, FL where the sun always shines. Our team members are the true soul of ...

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Vacation Rentals information

What jobs pay you to go on vacation?

Jobs that pay you to go on vacation include travel bloggers, tour guides, cruise ship staff, and travel writers. These roles often involve travel-related skills, certifications, and the ability to work in dynamic environments, providing opportunities to visit different locations as part of the job.

What is the difference between an Airbnb and a vacation rental?

A vacation rental is a property rented out for short-term stays, often managed by individual owners or property managers, while Airbnb is an online platform that connects travelers with hosts offering vacation rentals. Airbnb listings can include various types of properties, such as apartments, houses, or unique accommodations, and require hosts to create profiles and manage bookings through the platform.

What is the difference between Vacation Rentals vs Property Managers?

AspectVacation RentalsProperty Managers
CredentialsTypically no formal credentials requiredMay require real estate or property management licenses
Work EnvironmentIndividual properties, online platformsMultiple properties, office settings, on-site visits
Employer & IndustryOwners, online rental platformsProperty management companies, real estate firms
Search & Comparison IntentFinding short-term rental optionsManaging rental properties, overseeing operations

Vacation Rentals involve listing and renting out individual properties for short-term stays, often managed directly by owners or through online platforms. Property Managers oversee multiple rental properties, handling maintenance, tenant relations, and operational tasks. While Vacation Rentals focus on guest experience and property listing, Property Managers coordinate the overall management of rental portfolios. Both roles are essential in the rental industry but serve different functions and require different skill sets.

What are vacation rentals?

Vacation rentals are properties that are rented out to travelers on a short-term basis, typically for a few days to a few weeks. These can include houses, apartments, condos, cabins, or villas that offer amenities similar to a home, such as kitchens and multiple bedrooms. Vacation rentals are often booked through online platforms and provide an alternative to hotels, giving guests more privacy and flexibility during their stay. They are popular among families, groups, and travelers seeking unique or local experiences.

What are the main challenges faced by professionals managing vacation rentals, and how can they be addressed?

Professionals managing vacation rentals often face challenges such as maintaining high occupancy rates during off-peak seasons, addressing guest concerns promptly, and ensuring properties are well-maintained between stays. Effective communication with guests, leveraging dynamic pricing tools, and working closely with cleaning and maintenance teams are key strategies to overcome these hurdles. Building strong relationships with local service providers and staying updated on industry trends can also enhance guest satisfaction and operational efficiency.

How to find a job that pays you to travel?

Vacation rental companies, travel agencies, and remote work platforms often offer jobs that involve travel, such as property managers, travel consultants, or remote customer service roles. These jobs typically require strong communication skills, flexibility, and sometimes specific certifications or experience in hospitality or travel industries.

How much can you make with a vacation rental property?

Vacation rental hosts can earn varying income depending on location, property size, and occupancy rates, with average annual earnings ranging from a few thousand to over $50,000. Successful hosts often manage bookings through platforms like Airbnb or Vrbo and may need to handle maintenance, guest communication, and pricing strategies to maximize income.

What are the key skills and qualifications needed to thrive as a Vacation Rental Manager, and why are they important?

To thrive as a Vacation Rental Manager, you need strong organizational skills, property management experience, and a solid understanding of hospitality standards, often supported by relevant certifications or real estate licenses. Familiarity with property management systems (PMS), booking platforms like Airbnb or Vrbo, and digital marketing tools is essential. Excellent communication, conflict resolution, and customer service skills help you build positive guest relations and address issues promptly. These competencies are crucial for maximizing occupancy rates, ensuring guest satisfaction, and maintaining efficient operations in a competitive market.
What are popular job titles related to Vacation Rentals jobs in Florida? For Vacation Rentals jobs in Florida, the most frequently searched job titles are:
What job categories do people searching Vacation Rentals jobs in Florida look for? The top searched job categories for Vacation Rentals jobs in Florida are:
What cities in Florida are hiring for Vacation Rentals jobs? Cities in Florida with the most Vacation Rentals job openings:
Vacation Rentals jobs near you
Infographic showing various Vacation Rentals job openings in Florida as of June 2026, with employment types broken down into 57% Full Time, and 43% Part Time. Highlights an 100% In-person job distribution.

Guest Relations at Old Town Vacation Homes

Historic Tours of America

Key West, FL • On-site

$18 - $21/hr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 23 days ago

Job description

Description
JOIN OUR OLD TOWN TROLLEY FAMILY! ®
This is a GREAT opportunity to SHINE the spotlight on your Guest Services skills!
This Guest Relations position assists guests with making and confirming reservations, registering, issuing keys, keeping records of occupied homes and condos, and presenting statements and collecting payments from guests. Assist guest requests for housekeeping and maintenance. Arrange or give advice on transportation, business services or entertainment. The Guest Relations position is to communicate information accurately and with pride and enthusiasm. Our guests judge our company by the way you handle yourself at work.
Employee Benefits
  • Competitive pay: $18 - $21 per hour
  • Schedule: Saturday - Wednesday
  • All FT Employees are eligible for paid vacation
  • Company sponsored health and wellness plans, including medical, dental, vision and many others
  • All FT, PT and Seasonal employees are eligible for: paid sick time, 401K plan with company matching*, fun and upbeat work environment with various award and recognition celebrations throughout the year, First Stop Health (a tele-health benefit 100% employer paid), discounts in retail stores, and free admission to all company attractions

*Eligibility requirements may apply
Operating tours, attractions and retail in Boston, Charleston, Key West, Nashville, San Antonio, San Diego, St. Augustine, Savannah, and Washington, DC since 1980!
Requirements
Essential Functions
  • Make and confirm reservations
  • Answer telephones in a courteous, professional manner
  • Respond promptly to emails
  • Compute bills, collect payments, and make change for guests
  • Issue keys and give directions to vacation rentals.

Required Knowledge, Skills, and Abilities
  • High degree of self-motivation and the ability to work independently or as a team within the scope of established rules and regulations.
  • Knowledge of principles and processes for providing customer and personal services. This includes customer needs assessment, meeting quality standards for services, and evaluation of customer satisfaction.
  • Knowledge of administrative and clerical procedures and systems such as work processing, emails, create worksheets/spreadsheets, input and retrieve data from a computer, managing files and records, and other office procedures and terminology.
  • Have a demonstrated a broad knowledge of Key West restaurants, attractions, and points of interest.
  • Have demonstrable math and sales skills.

Qualifications
  • High school graduate or equivalent preferred.
  • Guest service experience preferred.

Other Requirements
  • Must pass pre-employment MVR/background check and substance abuse testing.
  • Valid FL Driver's License with acceptable driving record for the past three years.
  • Have a passion for helping people and making their Key West experience a memorable one.

Apply