Description
COMPANY OVERVIEW:
The Cottages on The Key is a luxury vacation rental management company in Siesta Key, Florida. We are dedicated to providing exceptional hospitality and sharing the best experiences in the area with guests from around the world.
We also offer comprehensive property management services for vacation rental owners. Our personalized "white glove" services are tailored to meet the financial goals and unique qualities of each property, resulting in our success and continued growth.
At The Cottages on The Key, we prioritize our culture. We foster a supportive and inclusive environment where everyone is valued. Our team is united and collaborative, allowing us to maintain an excellent work-life balance.
POSITION SUMMARY:
The Cottages on the Key is looking for someone who’s driven and wants to grow with us—someone who enjoys having independence in their work and finds meaning in what they do. We believe that working together helps everyone grow, stay open, and succeed. This is a full-time role with lots of room to take on more responsibility and grow into new opportunities. You’ll be part of an encouraging, and fast-paced team that really values your perspective and development.
As our Bookkeeping and Administrative Assistant, you’ll be a key part of the team, helping out across departments like accounting, operations, marketing, and acquisitions. You’ll handle regular bookkeeping tasks—daily, weekly, and monthly—and jump in with general admin support wherever it’s needed. That includes supporting multiple departments on the daily, keeping an eye on office supplies and placing standard orders when we’re running low, and helping out with planning office events like leadership meetings, holiday parties, and our annual get-togethers. You’ll also track employee anniversaries and birthdays, and use the company card to purchase gifts—basically making sure everyone feels celebrated and appreciated. You’ll wear a lot of hats, but your work will definitely make a difference.
RESPONSIBILITIES:
- Provide cross-department collaboration and overall logistical support through clear communication, organization, and critical thinking
- Bookkeeping tasks include processing receipts & invoices, creating & entering bills into Quickbooks, filing & organizing hard copy and digital files into Google Drive, and sending payments via Quickbooks online.
- Create ad hoc financial reports using Quickbooks and Excel/Sheets for various projects & requests for information by departments, vendors, and homeowners
- Communicate with owners, guests, and vendors through email and phone for various purposes including but not limited to: gathering documents and responding to requests for information regarding revenue, expenses, invoices, charges, compensations
- Become familiar with the inventory of all homes, components, amenities, and experiences we offer in the area
- Export work orders from property management software to process maintenance payments and add to owner statements for billing
- Send payment reports to maintenance personnel
- Monitor bills input into Quickbooks for accuracy of account and property and help fix any billing or payment issues that arise with vendors
- Monitor the administrative department email for receipts from internal personnel
- Bill owners for items purchased from in-house inventory
- Assist in processing month-end financial statements for property owners
QUALIFICATIONS:
- Willing to train on everything, but must be a quick learner and familiar with technology
- Vacation rental industry experience is a plus.
- Quickbooks experience is a bonus. Knowledge of trust accounting is a plus.
- Quick learner of technology and apps.
- Strong work ethic, with the ability to multitask.
- Ability to work in an ever-changing environment while maintaining a high standard of accuracy.
- Familiarity with accounts payable
- High attention to detail and accuracy a MUST
- Ability to work on repetitive tasks and maintain a high-level of work
COMPENSATION & BENEFITS:
Annual Salary: $40,000 - $50,000
Benefits
- Paid time off such as PTO, sick days, and vacation days
- Health insurance
- Employee recognition programs
- Workplace perks such as recreation activities, food and coffee, and flexible work schedules
Schedule
- Training Tues-Saturday 9am - 5pm
- Regular Schedule Monday-Friday 9am - 5pm