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Contractual Remote Vacation Rental Jobs in Florida

Better Talent

Revenue Manager

Key West, FL · Remote

$80K - $100K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • PTO

Company Overview Seven Keys Vacations is a locally led vacation rental management company serving ... Comfortable operating with independence in a remote, results-oriented environment. Compensation ...

Lemon Juice

Group Sales Coordinator

Orlando, FL · On-site +1

$25/hr

Fully remote. May have to work in different time zones. Experience with inventory mapping, PMS ... Experience working with vacation rental software, OTAs, or channel management platforms preferred.

Vacatia

Call Center Confirmer

Orlando, FL · Remote

$16/hr

Remote (Work from home in Florida) Employment Type: Full-Time Compensation: $16 hourly + commission Vacatia is an innovative hospitality company reinventing the vacation rental and ownership ...

MHI

Engineer III, Remote Commissioning

Lake Mary, FL · On-site +1

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

Ensure compliance with internal standards, contractual obligations, and regulatory requirements ... Paid vacation, sick time, and holidays. * Committed to quality products and services. * Great ...

MHI

Senior Engineer, Remote Commissioning

Lake Mary, FL · On-site +1

$91K - $125K/yr

  • Medical

  • Dental

  • Vision

  • Retirement

  • PTO

... safety, schedule, contractual risk, and long-term reliability. * Serve as senior technical ... Paid vacation, sick time, and holidays. * Committed to quality products and services. * Great ...

SLM Bookings

Remote Booking Agent

Miami, FL · Remote

$35K - $62K/yr

Free to Discounted vacations for you and your family * A community of other agents, remember even ... Book travel needs (airline, car rental, hotel accommodations, cruise, ticket/event sales, etc.

VTrips

Owner Success Manager

Jacksonville, FL · Remote

$45K - $50K/yr

... of vacation homes while ensuring an exceptional partner experience. This is an ideal opportunity ... This is a remote position. Candidates must reside in either AL, FL, GA, MD, NM, NC, SC, TN, or TX ...

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All JobsContractual Vacation Rental JobsContractual Remote Vacation Rental JobsContractual Remote Vacation Rental Jobs in Florida

Contractual Remote Vacation Rental information

What is the difference between Contractual Remote Vacation Rental vs Contractual Remote Property Manager?

AspectContractual Remote Vacation RentalContractual Remote Property Manager
CredentialsTypically requires knowledge of hospitality, rental laws, and customer serviceRequires real estate, property management certifications, and legal knowledge
Work EnvironmentPrimarily remote, managing rental listings, guest communication, and bookingsRemote or on-site, overseeing property operations, maintenance, and tenant relations
Industry UsageUsed in travel, hospitality, and short-term rental sectorsCommon in real estate, property management firms, and leasing companies

Contractual Remote Vacation Rental involves managing short-term rental listings and guest interactions remotely, focusing on hospitality services. In contrast, Contractual Remote Property Managers handle broader property oversight, including maintenance and tenant relations, often requiring real estate credentials. Both roles are remote but serve different aspects of property management within the rental industry.

What are the most commonly searched types of Remote Vacation Rental jobs in Florida?

The most popular types of Remote Vacation Rental jobs in Florida are:

What are popular job titles related to Contractual Remote Vacation Rental jobs in Florida?

For Contractual Remote Vacation Rental jobs in Florida, the most frequently searched job titles are:

What job categories do people searching Contractual Remote Vacation Rental jobs in Florida look for?

The top searched job categories for Contractual Remote Vacation Rental jobs in Florida are:

What cities in Florida are hiring for Contractual Remote Vacation Rental jobs?

Cities in Florida with the most Contractual Remote Vacation Rental job openings:

Contractual Remote Vacation Rental jobs near you
Infographic showing various Contractual Remote Vacation Rental job openings in Florida as of August 2026, with employment types broken down into 71% Full Time, and 29% Part Time. Highlights an 100% Remote job distribution.

Sales Executive - Real Estate & Vacation Rental Media

Better Talent

Kissimmee, FL • Remote

$100K/yr

Full-time, Contractor

Posted 7 days ago

Job description

Company Overview

CLICK Real Estate Photography & Video is a fast-growing media company specializing in high-end visual content for real estate and vacation rental brands across the U.S. and international markets.

We are not a traditional photography company. We are a strategic media partner helping property managers, realtors, and hospitality brands increase bookings, stand out online, and scale their business through powerful visual storytelling.

With a presence in Orlando, Miami, Tampa, California, Aruba, and beyond, CLICK is rapidly expanding and building a national network of top-tier creatives.

We move fast, deliver in 24 hours, and operate with high standards. If you are energized by people, motivated by results, and excited about growing with a company on the rise, this is your opportunity to get in early and make an impact.

Position Summary

We are seeking a Sales Executive to drive new business across the real estate and vacation rental industries.

This role is centered around building relationships, generating opportunities, and turning conversations into long-term partnerships. You will be responsible for identifying prospects, presenting our services, and helping clients understand how high-quality media can directly impact their bookings and growth.

This is a performance-driven, independent contractor role designed for someone who thrives in a fast-paced, people-focused environment. Success in this role comes from your ability to connect quickly, communicate with confidence, and influence decision-makers.

This role is structured to reward performance through commission and recurring revenue, allowing you to build a growing monthly income stream over time.

What You’ll Do

  • Prospect and generate new leads through outreach (calls, email, social, networking)

  • Pitch CLICK services to real estate agents, brokers, and vacation rental managers

  • Build rapport quickly and guide conversations toward meaningful business opportunities

  • Close new clients and support onboarding

  • Develop and maintain long-term client relationships

  • Collaborate with internal teams to ensure smooth execution

  • Identify upsell opportunities, including video, drone, and Matterport services

Required Qualifications

  • Proven experience in sales (real estate, vacation rental, or media is a strong plus)

  • Strong communication skills with the ability to engage, influence, and build trust quickly

  • Confident, outgoing, and comfortable initiating conversations with new people

  • Self-starter with a high level of initiative and ownership

  • Comfortable working in a flexible, fast-moving environment with changing priorities

  • Organized and results-driven

Compensation, Benefits & More

On-Target Earnings (OTE): $100,000+ (salary + commission based on performance)

Benefits:

  • Flexible, remote-first work environment

  • Opportunity to build and grow your own book of business

  • Recurring income model tied to long-term client relationships

  • Clear path to increase earnings as your client base grows

  • High-visibility role within a fast-scaling company