Thirty Years In. Still the First Call.
At Annie and Company, we specialize in helping rental property managers thrive in a competitive market. Our journey began with a simple mission: to provide unparalleled support and guidance. We believe in building lasting partnerships based on trust, communication, and results.
Meet Our Chief STRategist
Annie Holcombe is a vacation rental industry strategist and founder of Annie & Co., a consulting firm serving property managers and technology companies in the short-term rental space. With over 30 years of experience across property management, online travel, channel distribution, and brand development, Annie is one of the most connected and widely respected figures in the vacation rental industry.
Her career includes senior roles at Expedia Group, Lexicon Travel, Homes & Villas by Marriott Bonvoy, and NextPax. She works with property managers who have 20 or more properties and need systems for owner acquisition, direct booking, and distribution optimization, and with technology companies that need credible access to the vacation rental market.
She is a VRMA board member, conference speaker, and co-host of the Alex and Annie Podcast. Every engagement runs through her proprietary STRive Method: Discover, Analyze, Architect, Activate, Optimize.
Read More about Annie's Journey
My journey in hospitality began unexpectedly, starting at a hotel front desk in 1992. Recognized for my knack for hospitality and communication, I transitioned to sales and marketing, furthering my career by leading business development and events for a growing condominium resort company. I collaborated with major brands and events, contributing to significant growth in the Panama City Beach market. What started out as a 625 Room resort quickly became one of the largest vacation rental management companies in the panhandle with 11+ condo properties and 3000 rooms under COA/HOA management and 1500+ on rental.
In 2008, I co-founded Oaseas Resorts, where I discovered a passion for vacation rental storytelling and online distribution. When I left the company, we had 800 vacation rentals on our program. The complexity and frustration with online travel led me to join Expedia in 2012 as a Market Manager for Northwest Florida and Gulf Shores, Alabama. I was fortunate enough to be part of a small team of market managers that advocated for vacation rentals to help transform how online travel agencies viewed the vacation rental market.
At Expedia, I managed alternative lodging accounts, working with industry leaders like Wyndham Vacation Rentals and Diamond Resorts. After four years at Expedia, I embarked on a new venture, being a founding member of Lexicon Travel in 2017. Our goal: to be pioneers in white-glove channel management for vacation rentals. Our team took great pride in working 1:1 with our property managers to provide top notch service with a consultative approach to distribution.
Since then, I have worked for Homes & Villas by Marriott Bonvoy and most recently global leader in channel management, NextPax. Through all of this, I have been given the opportunity to engage with property managers from around the world. The relationships I’ve nurtured over the years, allow me to advocate for vacation rentals to be the most recognized and celebrated segment in travel. Today, I am now thrilled to bring this experience and expansive network to the industry at large.
Affiliations
Right to Rent Collaborative • Advisory Committee Member
VRMA Board Member
VRMA Membership Committee 2023-Current
VRMA International Conference Planning Committee: 2025 Conference
Explorabout Advisory Board Member: December 2024- December 2025
Whimstay September 2021-October 2022
Get in Touch with Us
Have questions or need assistance? We are here to help you navigate your rental property challenges. Reach out to schedule a consultation today!