Top Vacation Rentals Startups in 2027

PriceLabs (chicagobusiness.com/innovators/what-if-you-could-adjust-prices-meet-demand) is a cloud-based software for vacation and short-term rentals to help them dynamically manage prices just the way large hotels and airlines do! Our mission is to help small businesses in the travel and tourism industry by giving them access to advanced analytical systems that are often restricted to large companies.

Hostaway has become a market leader in marketing, sales, management, reporting and communication for vacation rental property managers. One of the largest marketplaces in the industry and deep integrations with Airbnb, VRBO, Expedia, HomeAway, Bcom, etc, property managers can increase exposure while saving time and money. Have a unique business model? We are the most versatile solution available. Trusted by thousands of property managers, Hostaway is known for stability, performance and service.

Wheelhouse is a FinTech platform for flex rentals. More specifically, Wheelhouse is a revenue & financial intelligence platform that empowers the next generation of hospitality & “flex living” operators. (Think “Shopify meets Hospitality”) Today, thousands of businesses manage their revenue, sales & analytics on top of Wheelhouse’s growing pricing & financial intelligence platform. At our foundation is our best-in-class machine learning price recommendation engine, which focuses on determining the correct nightly price for the unique properties that sell in the short-term & flex rental space. Our pricing engine provably drives revenue performance 20%+, and is combined with data tools (market & competitive intelligence tools) that help professional teams manage inventory anywhere in the world. In 2021, our platform was named “Innovation of the Year” at the Data & Revenue Management conference - as voted on by one of our key customer targets. We’re a well-funded, collaborative & productive team that enjoys shipping beloved products, on time, while having fun, and partnering deeply with our customers to help drive their business success. Our team is best described as transparent & collaborative, and we strive to set our teammates up for success - both professionally & personally. Certainly, there is a lot more to share, and we’d be eager to say hello & learn more about you! To learn more about our platform: usewheelhouse.com To learn more about our data science: usewheelhouse.com/blog/wheelhouse-pricing-engine

Sonder is revolutionizing hospitality through innovative, tech-powered service and inspiring, thoughtfully designed accommodations combined into one seamlessly managed experience. Officially launched in 2014 and headquartered in San Francisco, Sonder is making a world of better stays open to all with a variety of accommodation options — from rooms to suites and apartments — found in 35 cities spanning eight countries and three continents. Sonder’s innovative app empowers guests by making self-service features and 24/7 on-the-ground support just a tap away. From simple self check-in to boutique bathroom amenities, we bring the best of a hotel without any of the formality.

Hospitable, an Inc. 5000 company, gifts short-term rental hosts their valuable time back. Founded in 2016, Hospitable’s tools allow hosts to automate the most time-consuming elements of hosting. Hosts use Hospitable to answer 90% of guest messages with AI-powered automated messaging, to automate their team notifications so they never miss a clean, and to avoid double bookings with a synchronized calendar across booking channels. Hospitable allows hosts to build their own direct booking website with guest vetting, $5M damage protection, and payment processing built-in. Hospitable also connects with popular 3rd party online travel agencies such as Airbnb, Vrbo, and [Booking.com](booking.com).

Vacatia Inc is an innovative hospitality company reinventing the timeshare experience across discovery, booking, and stay. Its online rental, subscription and brokerage platform makes it easy for families to vacation in a resort residence, with the space of a home and services of a hotel. The customer can choose to stay as a renter, subscriber, or owner. While the online platform is used by a wide number of partner resorts, the company also directly manages independent timeshare properties. By providing tech-enabled hospitality and renovation services, Vacatia revives older timeshare resorts to appeal to a modern audience.

Breezeway makes it easier to manage property care and maintenance operations. Our mobile solution helps property managers and owners coordinate cleaning and maintenance tasks, improving quality and ensuring the job gets done right. Using property inventory and smart templates, vacation rental managers, owners, cleaning services and contractors use our software tools in the field to keep their property well-maintained, their operations running smoothly and their clients happy. Created by the founder of FlipKey and the team that grew vacation rentals into a world-class product at TripAdvisor, we're backed by leading investors in the real estate space and building the tools that will define the future of how we interact with property.

Clearing is a very fast growing tailored solution for Short-Term Rental property managers to automate accounting and expense management. Already helping hundreds of property managers!

Avacasa is a platform that helps Buyers discover and invest into holiday homes.