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Seasonal Short Term Rentals Jobs in Massachusetts

Better Talent

Property Caretaker

Yarmouth Port, MA · On-site

$25 - $35/hr

Interest in real estate, hospitality, home improvement, or short-term rentals. * Basic handyman ... position follows the seasonal nature of Cape Cod hospitality. * Peak Season (June-August)

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Seasonal Short Term Rentals information

What are seasonal short term rentals?

Seasonal short term rentals are properties that are leased out to tenants for brief periods, typically ranging from a few days to several months, and are most often available during peak vacation or holiday seasons. These rentals are popular in tourist destinations and provide an alternative to hotels, offering amenities like kitchens and private living spaces. Property owners often use platforms like Airbnb or VRBO to list their seasonal rentals, catering to travelers looking for flexibility and comfort. Regulations and requirements for operating such rentals can vary widely depending on the location, so it's important for both owners and renters to research local laws.

What are the key skills and qualifications needed to thrive as a seasonal short term rental manager?

To thrive as a Seasonal Short-Term Rental Manager, you need strong organizational skills, attention to detail, and knowledge of property management, often supported by experience in hospitality or real estate. Familiarity with booking platforms like Airbnb or Vrbo, property management software, and local rental regulations is typically required. Excellent communication, problem-solving abilities, and customer service skills help you effectively address guest needs and coordinate with service providers. These skills ensure smooth operations, high guest satisfaction, and compliance with regulations during peak rental seasons.

What are some common challenges faced when managing seasonal short term rentals, and how can they be addressed?

Managing seasonal short term rentals often involves handling fluctuations in guest demand, which can lead to periods of high intensity and downtime. During peak seasons, quick turnovers and maintaining property standards become crucial, requiring excellent time management and coordination with cleaning and maintenance teams. Off-season periods may involve strategizing marketing efforts to attract bookings and performing property upgrades. Building strong relationships with local service providers and using property management software can help streamline operations and reduce stress during busy times.

What is the difference between Seasonal Short Term Rentals vs Property Manager?

AspectSeasonal Short Term RentalsProperty Manager
CredentialsNone required, but knowledge of local regulations helpsReal estate or property management certifications often preferred
Work EnvironmentIndividual or small team managing short-term rentals, often remotelyOversees multiple properties, may work on-site or remotely
Employer & IndustryHospitality, real estate, vacation rental platformsReal estate firms, property management companies

Seasonal Short Term Rentals involve managing or hosting short-term rental properties, focusing on guest experience and property upkeep. Property Managers oversee multiple rental units, handling maintenance, tenant relations, and operational tasks. While both roles require knowledge of local regulations and customer service skills, Property Managers typically have more formal credentials and broader responsibilities across multiple properties.

What are the most commonly searched types of Short Term Rentals jobs in Massachusetts?

The most popular types of Short Term Rentals jobs in Massachusetts are:

What cities in Massachusetts are hiring for Seasonal Short Term Rentals jobs?

Cities in Massachusetts with the most Seasonal Short Term Rentals job openings:

Seasonal Short Term Rentals jobs near you

Property Caretaker

Better Talent

Yarmouth Port, MA • On-site

$25 - $35/hr

Full-time

PTO

Re-posted 8 days ago

Job description

Company Overview

Beacon Destinations is a fast-growing boutique hospitality company redefining the vacation rental experience across Cape Cod. We combine the warmth and character of locally owned vacation homes with the operational excellence of a luxury hotel brand, creating unforgettable stays for guests while protecting and maximizing value for homeowners.

Our mission is simple: deliver exceptional, five-star experiences on every stay. Through innovative technology, hands-on local service, and an unwavering commitment to quality, we're setting a new standard for coastal hospitality.

Position Summary

As a Property Caretaker at Beacon Destinations, you'll be the hands-on guardian of our Cape Cod vacation homes, ensuring every property is guest-ready, well maintained, and cared for to the highest standards. You'll perform property inspections, light maintenance, preventative upkeep, and occasional guest support while working independently across a portfolio of homes.

This role is ideal for someone who enjoys solving problems, takes pride in quality workmanship, notices the details others miss, and wants every guest and homeowner to have complete confidence that their property is in excellent hands.

Key ResponsibilitiesProperty Care

  • Complete detailed inspections before guest and homeowner arrivals.

  • Ensure homes are clean, safe, fully stocked, and guest-ready.

  • Perform preventative maintenance and minor repairs including changing light bulbs, adjusting doors, unclogging drains, replacing batteries, and other routine tasks.

  • Identify maintenance issues and coordinate larger repairs with vendors and management.

Guest & Homeowner Support

  • Respond professionally to guest and homeowner questions, service requests, and maintenance concerns.

  • Assist with escalated issues alongside the Operations team to ensure timely resolution.

Portfolio Operations

  • Support onboarding of new properties by assisting inspections, setup, and quality standards.

  • Identify opportunities to improve operational efficiency and guest experience.

  • Collaborate across departments to support changing business needs.

Other duties as assigned because every day is different in hospitality!

Required Qualifications

  • Minimum 1 year experience required in housekeeping, maintenance or property inspection role

  • Vacation rental, hotel, or hospitality experience strongly preferred.

  • Comfortable performing basic home maintenance and troubleshooting common household issues.

  • Excellent organizational and time management skills with the ability to prioritize changing workloads.

  • Strong attention to detail and commitment to quality.

  • Comfortable using smartphones, mobile apps, and digital work order systems.

  • Excellent communication and customer service skills.

  • Self-motivated with the ability to work independently while contributing to a collaborative team.

  • Reliable transportation and willingness to travel throughout Cape Cod daily.

  • Available to work weekends, holidays, evenings, and flexible schedules based on business needs.

  • Able to lift up to 50 pounds and perform the physical requirements of the role.

Preferred Qualifications

  • Experience working with vacation rentals or residential property management.

  • Interest in real estate, hospitality, home improvement, or short-term rentals.

  • Basic handyman, carpentry, plumbing, electrical, or maintenance experience.

Compensation & BenefitsSalary $25-$35 per hour, based on experience.Bonus

  • Earn up to $2,000 annually based on guest satisfaction scores, property performance, and overall portfolio quality.

Benefits

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

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

Schedule

This position follows the seasonal nature of Cape Cod hospitality.

  • Peak Season (June-August): Approximately 40 hours per week.

  • Shoulder Seasons (March-May & September-December): Approximately 20 hours per week.

  • Hours may vary based on occupancy levels, weather, maintenance priorities, and guest needs.