Highgate is a leading real estate investment and hospitality management company with over $15 billion of assets under management and a global portfolio of more than 400 hotels spanning North America, Europe, the Caribbean, and Latin America. With a 30-year track record as an innovator in the hospitality industry, this forward-thinking company provides expert guidance through all stages of the property cycle, from planning and development through recapitalization or disposition. Highgate continues to demonstrate success in developing a diverse portfolio of bespoke lifestyle hotel brands, legacy brands, and independent hotels and resorts, featuring contemporary programming and digital acumen. The company utilizes industry-leading revenue management tools that efficiently identify and predict evolving market dynamics to drive outperformance and maximize asset value. With an executive team of seasoned hospitality leaders and corporate offices worldwide, Highgate is a trusted partner for top ownership groups and major hotel brands. www.highgate.com

Discover more sun and more fun! Escape to a tropical beachfront paradise complete with everything you need for the perfect getaway, including delicious dining, beachfront bars, relaxing comforts, and endless activities. Here you’ll stay at one, play at two — with two connecting resorts right on the soft white sands of St. Pete Beach. Whether you’re looking for family fun, a romantic retreat, a group getaway, or anything in between, it’s all here at TradeWinds Island Resorts. https://www.tradewindsresort.com/careers

Follow your passion all the way to paradise at TradeWinds Resort! Located along the gorgeous Gulf Coast on St. Pete Beach, a Top-Ranked U.S. Beach, TradeWinds features two destination resorts just 200 flip-flops from one another. 

We’re proud to share that our management company, Highgate, has been recognized as a 2026 USA TODAY Top Workplaces award winner. When you join the TradeWinds team, you become part of a culture that values passion, collaboration, excellence, purpose, and inclusivity. If you’re passionate about creating memorable experiences and making a meaningful impact, we’d love to meet you. Bring your passion to paradise and discover where your career can take you at TradeWinds! 

Join a company where Our People are at the heart of everything we do. 

The Groundskeeper is responsible for maintaining the cleanliness and appearance of the resort grounds by sweeping walkways and common areas, removing litter and other debris, emptying and cleaning trash receptacles, and returning trash cans to their designated locations. Ensure all outdoor areas remain clean, orderly, and presentable for guests and staff.

• Maintain the overall cleanliness, appearance, and presentation of the property to ensure a welcoming environment for all guests.

• Sweep sidewalks, walkways, entrances, patios, and other outdoor areas, removing dirt, leaves, litter, and debris.

• Inspect all grounds and remove any man-made items, trash, or debris that may affect the appearance of the property.

• Check all trash cans and ashtrays throughout the property, ensuring they are emptied, cleaned, and returned to their proper locations.

• Inspect and clean the main lobby area, entrances, and surrounding walkways to maintain a neat and presentable appearance.

• Inspect all pool areas to ensure they are clean, orderly, and presentable for guests.

• Remove trash and debris from pool decks, surrounding walkways, lounge areas, and other designated outdoor spaces.

• Inspect the waterways and waterfront areas for trash, litter, and floating debris, removing items as appropriate and reporting any concerns.

• Monitor landscaping, gardens, and green spaces for litter, fallen branches, leaves, and other debris.

• Ensure outdoor furniture, lounge chairs, tables, and other resort amenities are clean, organized, and returned to their designated locations.

• Check resort entrances, parking areas, and common areas for trash and maintain a clean, professional appearance.

• Identify and report maintenance issues, safety hazards, damaged property, or unsanitary conditions to the appropriate department.

• Follow resort cleanliness, safety, and sanitation standards while performing daily duties.

• Respond promptly to guest requests and maintain a courteous, professional attitude when interacting with guests and team members.

• Use cleaning equipment and supplies properly and safely while completing assigned tasks.

• Conduct routine inspections of assigned areas throughout the shift to ensure cleanliness standards are consistently maintained.

• Assist other departments with cleaning and groundskeeping needs as necessary.

• Perform other duties as assigned by management.

We are pleased to offer to our full-time associates a comprehensive and competitive benefits package designed to support your health, well-being, and financial future.

• Medical insurance, dental insurance, vision insurance, life insurance, short-term and long-term disability insurance
  401(k) Retirement Plan with employer matching contributions
• Paid holidays
• Paid vacation
• Paid sick leave (provided in accordance with applicable law)
• Employee assistance program (EAP)
• Educational opportunities / Tuition reimbursement
• Paid jury duty leave, personal leave, medical leave, and military leave in accordance with applicable law

For Employees Based in Washington:

• 8 paid holidays per year
• Up to 20 days of paid vacation per year, based on classification and length of service
• Paid Sick & Safe Time accrues at 1 hour for every 30 hours worked, with up to 72 hours of unused time carried over from one anniversary year to the next.

For Employees Based in Colorado:

• 8 paid holidays per year; employees working in the City of Denver receive 64 hours of designated holiday time per calendar year
• Up to 20 days of paid vacation per year, based on classification and length of service
• 6 days or 48 hours of Paid Sick Leave per year, accrued at 1 hour for every 30 hours worked.

For Employees Based in California:

• 8 paid holidays per year
• Up to 20 days of paid vacation per year, based on classification and length of service, capped at 1.5x annual accrual rate; non-supervisory employees working in the City of Los Angeles accrue up to 22 days of Compensated Time Off, based on length of service capped at 192 hours of combined PST and CTO.
• Paid Sick Time accrues at 1 hour for every 30 hours worked, unused time is carried over from one anniversary year to the next up to a maximum of 80 hours; employees working in the City of Los Angeles are provided 40 hours of Paid Sick Time annually on their anniversary, unused time is not carried over from one anniversary year to the next.

Please note that certain benefits described above for associates in Washington, Colorado, and California may vary for associates covered by a Collective Bargaining Agreement (“CBA”). For such associates, eligibility for and the terms and conditions of benefits are governed by the applicable CBA and any applicable plan documents, and may differ from the benefits described above. In the event of any conflict or inconsistency, the terms of the applicable CBA and governing plan documents will control, as applicable.

**The above-referenced benefits do not apply to part-time positions

This job opening was posted on October 27, 2026 and will remain open for at least 14 days.