Premier/VIP Guest Liaison
The Cottages on the Key
Posted November 10, 2026
Job 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 Premier Guest Liaison is the go-to person for our most valued guests and our most challenging situations. This full-time, in-office role works Thursday through Monday, 9am–5pm, and is a natural fit for a warm, persuasive communicator who loves winning people over.
The role has three parts:
VIP guests. You’ll lead our VIP campaign and manage the VIP and potential-VIP pipeline. That means building relationships with high-value repeat guests and making sure every stay feels personal.
Escalations and relocations. When a reservation has to be moved or canceled, you’ll own it from start to finish: find a comparable home, rebook the guest, and turn a frustrating moment into a reason to come back.
Sales. You’ll make outbound sales calls and cover inbound inquiries on days when no other agent is working, including weekends.
A typical day might include:
Pre-arrival welcome calls to confirm details and set expectations
Outbound calls to past guests and VIP prospects to book their next stay
Handling an escalated reservation, including relocating a guest or approving a service-recovery credit
Visiting properties for walkthroughs or to welcome VIP guests
Answering inbound calls and emails, quoting, and booking reservations
Working with operations on property issues that affect upcoming guests
Who thrives here: someone warm, calm under pressure, and organized. You should enjoy building relationships, solving problems, and closing the sale. If you light up when you’re talking with people and take pride in turning a good conversation into a booked stay and a loyal guest, you’ll thrive here.
What You'll Do
Lead the VIP campaign: run outreach and rebooking to keep top guests coming back.
Manage the VIP / PVIP pipeline: track current VIPs and potential VIPs, and move prospects into VIP status.
Outbound sales calls: call past and prospective guests to book stays.
Pre-arrival welcome calls: call guests before arrival to confirm details and set expectations.
Property visits: drive to properties for walkthroughs and VIP welcomes.
Support inbound sales coverage: answer inquiries, quote, and book reservations.
Support the weekends: cover Saturday and Sunday guest and sales needs.
Retention / relocations: when a stay has to be moved or canceled, find a comparable unit, rebook the guest, and keep the revenue.
Resolve escalations: own guest problem accounts from start to finish, approving comps up to a set limit and escalating anything above it to the Sales Manager.
Required Qualifications
2+ years of customer-facing experience in vacation rentals, hotels or resorts, concierge, or hospitality reservations
Sales or reservations experience, such as booking, quoting, inside sales, or meeting a sales goal
Experience handling escalations or guest complaints, including service recovery, guest relations, or customer resolution
Lives in the Sarasota/Bradenton area and can commute daily to our office
Valid driver's license and reliable vehicle for property visits
Available Thursday–Monday, 9am–5pm, including weekends
Comfortable with reservation software (a PMS, CRM, or booking platform) and with Google Workspace
Preferred Qualifications
Experience with StreamlineVRS or another vacation rental property management system (Track, Escapia, Guesty, etc.)
Vacation rental experience specifically, especially in a coastal or resort market
Knows the local area, including Siesta Key, Lido Key, Anna Maria Island, and Sarasota neighborhoods, restaurants, and attractions
Luxury or VIP service background, such as high-end hotels, private clubs, or travel concierge work
Track record of hitting sales goals or earning commission or bonuses
Experience with outbound or relationship-based sales, such as repeat-client outreach or pipeline management
Compensation, Benefits & More
Annual Salary: $60,000–$70,000 depending on experience
Bonus: Commission on reservations made
Benefits:
Paid time off, including vacation and sick days
Health insurance
Workplace perks such as recreation activities, food and coffee, and flexible work schedules
Schedule: Thursday through Monday, 9AM to 5PM
Job Type: Full-time
Location: On-site in Siesta Key, FL