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Vacation Rental Assistant Jobs in Massachusetts (NOW HIRING)

Better Talent

Property Caretaker

Yarmouth Port, MA

$25 - $35/hr

... * Assist with escalated issues alongside the Operations team to ensure timely resolution ... Vacation rental, hotel, or hospitality experience strongly preferred. * Comfortable performing ...

Del Mar Vacations

Guest Experience Coordinator

Orleans, MA · On-site

$22 - $28/hr

Support early check-in coordination and approval workflows * Assist with documentation and record ... vacation rental company on Cape Cod. We specialize in providing 5-star experiences to our guests ...

First Realty Management

Management Assistant

East Boston, MA · On-site

$45K - $52K/yr

They will also assist in the coordination of rental activities and address residents' general ... Paid Vacation, Holidays, PTO/Personal leave. * 401(k) plan. * Health, Vision, and Dental Insurance.

First Realty Management

Management Assistant

Roslindale, MA · On-site

$44K - $50K/yr

They will also assist in the coordination of rental activities and address residents' general ... Paid vacation, holidays, PTO/personal leave. * 401(k) plan. * Health, vision, and dental insurance.

New England Baptist Hospital

Vacation Sick Bank (VSB): paid holiday, sick, and vacation leave. Housing: Arranged individually by ... Assistance navigating Boston real estate and rental market provided through program office.

The Salvation Army Eastern Territory

Driver

Canton, MA · On-site

$15 - $20/hr

Generous paid time off every year that includes: holidays, vacation time and sick time * Employer ... Unload truck and assist with setup as needed. * Return truck to rental location. * Remain up to ...

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Vacation Rental Assistant information

See Massachusetts salary details

$12

$23

$37

How much do vacation rental assistant jobs pay per hour?

As of Aug 30, 2026, the average hourly pay for vacation rental assistant in Massachusetts is $23.67, according to ZipRecruiter salary data. Most workers in this role earn between $17.31 and $26.25 per hour, depending on experience, location, and employer.

What does a vacation rental assistant do?

A Vacation Rental Assistant supports property owners or managers by handling day-to-day tasks related to vacation rental properties. Their duties often include communicating with guests, coordinating check-ins and check-outs, managing bookings, and overseeing cleaning and maintenance schedules. This role ensures guests have a smooth experience and that the property is well-maintained. Vacation Rental Assistants may also help with marketing the property and responding to guest inquiries promptly.

What are the key skills and qualifications needed to thrive as a vacation rental assistant, and why are they important?

To thrive as a Vacation Rental Assistant, you need strong organizational skills, attention to detail, and experience in hospitality or property management. Familiarity with property management systems (PMS), online booking platforms like Airbnb or VRBO, and basic maintenance tools are often required. Excellent communication, customer service orientation, and problem-solving abilities help you stand out in this role. These skills ensure smooth operations, satisfied guests, and positive reviews, which are crucial for business success in the vacation rental industry.

What are some common challenges faced by vacation rental assistants, and how can they be managed effectively?

Vacation Rental Assistants often juggle multiple responsibilities, such as coordinating guest check-ins, handling last-minute maintenance requests, and ensuring properties are cleaned and ready on time. One of the main challenges is managing unexpected issues, like scheduling conflicts or guest concerns, while maintaining a positive guest experience. Staying organized, communicating clearly with property owners and cleaning staff, and using property management tools can help streamline daily tasks and reduce stress. Building strong relationships with vendors and having backup plans in place also contribute to smoother operations.

What is the difference between Vacation Rental Assistant vs Property Manager?

AspectVacation Rental AssistantProperty Manager
CredentialsBasic customer service, hospitality, or administrative skillsReal estate or property management certifications often preferred
Work EnvironmentAssists with daily rental operations, guest communication, and bookingsOversees entire property, handles maintenance, leasing, and tenant relations
Employer & IndustryVacation rental companies, hospitality industryReal estate firms, property management companies

While both roles involve managing rental properties, a Vacation Rental Assistant primarily supports daily operations and guest interactions, whereas a Property Manager oversees the entire property, including maintenance and tenant relations. The assistant role is more focused on hospitality tasks, making it ideal for those starting in the industry or seeking administrative experience.

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

The most popular types of Vacation Rental jobs in Massachusetts are:

What are popular job titles related to Vacation Rental Assistant jobs in Massachusetts?

For Vacation Rental Assistant jobs in Massachusetts, the most frequently searched job titles are:

What job categories do people searching Vacation Rental Assistant jobs in Massachusetts look for?

The top searched job categories for Vacation Rental Assistant jobs in Massachusetts are:

What cities in Massachusetts are hiring for Vacation Rental Assistant jobs?

Cities in Massachusetts with the most Vacation Rental Assistant job openings:

Vacation Rental Assistant jobs near you
Infographic showing various Vacation Rental Assistant job openings in Massachusetts as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $49,235 per year, or $23.7 per hour.

Property Caretaker

Better Talent

Yarmouth Port, MA

$25 - $35/hr

Full-time

PTO

Re-posted yesterday

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.