Best Online Travel Companies in Toronto, Canada
The 56 best Online Travel companies in Toronto, Canada in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Sherpa.
Ranked: Best Online Travel companies in Toronto
| # | Company | Disclosed funding | Last round | Stage | Founder | Founded | Tech stack | Recent signals |
|---|---|---|---|---|---|---|---|---|
| 1 | Sherpa Provider of AI-powered visa and travel authorization compliance solutions | $11M | 62 mo ago | Series A | Ivan Sharko Co-Founder | 2015 | WebflowApple iCloud MailGoogle Workspace+21 | 1 job opening · 2 partnerships |
| 2 | TripStack SaaS-driven flight distribution networks & itinerary solutions for OTAs | $6M | 96 mo ago | Acquired | John Boguslawski Business Development Executive & Co-Founder | 2016 | WixSentryApple iCloud Mail+15 | 1 partnership |
| 3 | CanadaStays Cottage, cabin and chalet rentals | $6M | 135 mo ago | Acqui-Hired | — | 2008 | — | — |
| 4 | PlanetEye Online travel guide and planning | $5M | 234 mo ago | Deadpooled | Jonah Sigel President & CEO | 2006 | — | — |
| 5 | Amgine AI-driven booking management & process automation system for business travelers | $4M | 33 mo ago | Series B | Jonathan Miller Founder | 2012 | WordPressMySQLPHP+17 | 1 partnership |
| 6 | Aya Provider of employee prepaid cards for healthcare payments | $3M | 67 mo ago | Seed | Chanddeep Madaan CEO and Founder | 2018 | WordPressMySQLPHP+37 | — |
| 7 | Lake Online marketplace for booking lake house rentals, cabins, and vacation homes | $3M | 9 mo ago | Seed | David Ciccarelli Co-Founder & CEO | 2023 | WordPress Block EditorWordPressMySQL+26 | 2 launchs |
| 8 | Necho System Automated expense management solution. | $2M | 306 mo ago | Acquired | Scott Anderson CEO & President | 1995 | — | — |
| 9 | BookSeats.com Online personalized holiday packages booking platform | $1M | 34 mo ago | Seed | — | 2019 | PHPLaravelNginx+33 | 1 partnership |
| 10 | SecondHome Online platform for booking vacation rentals | $600K | 164 mo ago | Deadpooled | Thomas Sampson Co-Founder | 2012 | — | — |
| 11 | Sitata Online platform that provides location-based health & other emergency information for travelers | $120K | 91 mo ago | Seed | Mark Pavlides Advisor to Founder | 2012 | BreakdanceWordPressMySQL+16 | — |
Top 12 Online Travel companies in Toronto
#1
Seed · Toronto, Ontario · founded 2023$2.6Mraised▾
Online marketplace for booking lake house rentals, cabins, and vacation homes. It provides a way for property owners to list their rentals. The platform offers search functionality based on dates, guests, and other preferences. It facilitates communication between guests and hosts through a secure messaging system. The platform also provides customer support to assist with issues.
- Sep 2025Seed$2.6M
- Seed—
#2
Series B · Toronto, Ontario · founded 2012 · 26 employees$3.8Mraised▾
AI-driven booking management & process automation system for business travelers. It offers a trip itinerary creation, client-agent interactions, TMC workflow management, and more.
- Sep 2023Series B$8.5M
- Apr 2022Series A$3.8M
#3
Series A · Toronto, Ontario · founded 2015 · 56 employees$11Mraised▾
Provider of AI-powered visa and travel authorization compliance solutions. The company offers a platform to complete visa applications and check travel requirements. It provides embeddable elements to purchase travel authorizations directly from websites. The company also offers an API to integrate real-time visa and entry services into existing platforms.
- Apr 2021Series A$8.5M
- Oct 2020Seed$2.5M
#4
Seed · Toronto, Ontario · founded 2019 · 3 employees$1.1Mraised▾
Online personalized holiday packages booking platform. Their platform enables travelers to search events they want to attend, build customized holiday packages based on their preferences & interests, as well as, make bookings via the platform by providing an online payment.
- Sep 2023Seed$1M
- Feb 2022Seed$50K
#5
Acquired · Toronto, Ontario · founded 2016 · 119 employees$6Mraised▾
SaaS-driven flight distribution networks & itinerary solutions for OTAs. Its product offering includes EFOE (Every Flight On Earth) and TripBuilder. EFOE is a flight booking API for OTAs that claims to integrate every low-cost airline (LCC) in the world. The TripBuilder is an API-based tool that uses big data & custom algorithms to analyze billions of airline route combinations & price points to produce low-cost flight itineraries.
- Jun 2018Series A$6M
#6
Seed · Toronto, Ontario · founded 2018 · 19 employees$2.9Mraised▾
Provider of employee prepaid cards for healthcare payments. It offers cards to advisors, employers, employees, and more. Funds are transferred to the healthcare card & monitored by the employers. It also enables employees to make healthcare payments for family members.
- Nov 2020Seed$2.9M
#7
Acqui-Hired · Toronto, Ontario · founded 2008 · 50 employees$6Mraised▾
CanadaStays is on online platform for cottage, cabin and chalet rentals. They have over 50,000 cottages, cabins and chalets for rent across Canada plus condos in major urban centres and vacation rentals in hot weather destinations in the US, Caribbean, and South and Central America. The site allows owners to update and manage their listings 24/7 publishing changes in real time, facilitate any or all communication between themselves and prospective travelers, and manage bookings.
- Apr 2015Series A$6M
#8
Deadpooled · Toronto, Ontario · founded 2006 · 11 employees$5Mraised▾
PlanetEye is an online travel guide and travel planning tool. Its website has a feature called Travel Pack which allows users to save in one place any attraction, hotel, or restaurant together. The company uses licensed technology from Microsoft Research to power its interface, creating a cool visual experience where maps are populated by images in small bubbles to highlight noteworthy locations. The company later pivoted its business model to focus on providing web technology and travel content to third parties.
- Jan 2007Series A$5M
#9
Acquired · Toronto, Ontario · founded 1995 · 61 employees$2.5Mraised▾
Necho provides expense management solutions to automate the processing and facilitate the management of employee business expenses. It provides valuable spend management data for vendor negotiations, preferred rates, spend analysis and other business intelligence. Enables management to implement, communicate, and enforce compliance of employee expense policies. Captures opportunistic savings such as VAT recoveries, timely and accurate re-billings, corporate card rebates and amounts recouped for income tax recovery. Necho was acquired by Cybershift Inc. in November 2005.
- Dec 2000Venture Debt$2.5M
#10
Deadpooled · Toronto, Ontario · founded 2012$600Kraised▾
SecondHome is a travel home rental in Canadian mountain destinations. Users can use SecondHome’s online platform to connect with home owners, book travel dates, and handle payments.
- Nov 2012Seed$600K
#11
Seed · Toronto, Ontario · founded 2012 · 20 employees$120Kraised▾
Online platform that provides location-based health & other emergency information for travelers. The app monitors health & safety threats such as disease outbreaks, violent protests, civil disruptions, extreme weather & provides location-based alerts for users. Provides emergency numbers, hospital locations, vaccination, and medication recommendations tailored to the user's itinerary. Users can also share their travel experiences on the app about safety and other local scams. The company also provides services to travel health practitioners, corporations, and insurance providers.
- Dec 2018Seed—
- 2018Seed$120K
#12
Seed · Toronto, Ontario · founded 2013 · 17 employees$25Kraised▾
NeoJets is an app-based platform to discover & book chartered flights. Travelers can book an on-demand flight a few hours prior to the departure. It provides a payment card that includes VIP transfers, access to exclusive events, boutique hotels, restaurants & deals on luxury brands. It provides NeoCard Black, NeoCard Teal & Credit Card. Their app is available for iOS & Android devices.
- Seed$25K
Funding & investor landscape
Notable founders
Market landscape — 10 sub-themes by coverage
Share of Online Travel coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising
Common questions
Rohit lives in the feed. He covers what's moving right now — the funding rounds, launches and shifts breaking across the trade press — and ties them back to where the sector is heading.