Best Online Travel Companies in Ontario, Canada
The 105 best Online Travel companies in Ontario, Canada in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Keep.
Ranked: Best Online Travel companies in Ontario
| # | Company | Disclosed funding | Last round | Stage | Employees | Founder | Tech stack | Recent signals |
|---|---|---|---|---|---|---|---|---|
| 1 | Keep Corporate cards and payment solutions for businesses 55Funding top 26%Tech top 27%Growth top 35%Moat top 38% All 9 signals ▾Fundingtop 26% Techtop 27% Growthtop 35% Moattop 38% Innovationtop 43% Patentstop 45% Talentbottom 49% Globalbottom 36% Marketbottom 34% Funding: Raised $76.0M across 3 rounds · 3 rounds over 1 yrs (3.0/yr) Tech: 50 technologies across 5/8 capability areas · Cloud: Amazon Ses, Amazon Web Services rank vs industry peers · Fliar Intelligence Index 55/100 | $76M | 13 mo ago | Series A | 41 | Helson Taveras Cofounder | SentryApple iCloud MailGoogle Workspace+33 | 2 job openings |
| 2 | Float Financial Solutions Virtual and physical corporate cards for expenses 48Tech top 33%Funding top 36%Growth top 45%Talent top 45% All 8 signals ▾Techtop 33% Fundingtop 36% Growthtop 45% Talenttop 45% Productbottom 48% Marketbottom 37% Globalbottom 36% Customersbottom 15% Tech: 44 technologies across 5/8 capability areas · Cloud: Amazon Ses, Amazon Web Services Funding: Raised $34.0M · 4 rounds over 5 yrs (0.8/yr) rank vs industry peers · Fliar Intelligence Index 48/100 | $34M | 28 mo ago | Series A | 86 | Rob Khazzam Co-Founder & CEO | SentryZendeskApple iCloud Mail+38 | — |
| 3 | RVezy Online RV rental platform | $23M | 60 mo ago | Seed | 87 | Michael McNaught Co-Founder | Apple iCloud MailGoogle WorkspaceNode.js+26 | 1 award |
| 4 | Sherpa Provider of AI-powered visa and travel authorization compliance solutions | $11M | 61 mo ago | Series A | 56 | Ivan Sharko Co-Founder | WebflowApple iCloud MailGoogle Workspace+21 | 1 job opening · 2 partnerships |
| 5 | TripStack SaaS-driven flight distribution networks & itinerary solutions for OTAs | $6M | 95 mo ago | Acquired | 119 | John Boguslawski Business Development Executive & Co-Founder | WixSentryApple iCloud Mail+15 | 1 partnership |
| 6 | CanadaStays Cottage, cabin and chalet rentals | $6M | 134 mo ago | Acqui-Hired | 50 | — | — | — |
| 7 | PlanetEye Online travel guide and planning | $5M | 233 mo ago | Deadpooled | 11 | Jonah Sigel President & CEO | — | — |
| 8 | Treepz App-based bus tickets booking platform | $4M | 40 mo ago | Seed | 68 | John Shaibu Co-Founder | Node.jsGoogle Sign-inTailwind CSS+12 | — |
| 9 | Amgine AI-driven booking management & process automation system for business travelers | $4M | 32 mo ago | Series B | 26 | Jonathan Miller Founder | WordPressMySQLPHP+17 | 1 partnership |
| 10 | Aya Provider of employee prepaid cards for healthcare payments | $3M | 67 mo ago | Seed | 19 | Chanddeep Madaan CEO and Founder | WordPressMySQLPHP+37 | — |
| 11 | Lake Online marketplace for booking lake house rentals, cabins, and vacation homes | $3M | 9 mo ago | Seed | — | David Ciccarelli Co-Founder & CEO | WordPress Block EditorWordPressMySQL+26 | 2 launchs |
| 12 | Necho System Automated expense management solution. | $2M | 305 mo ago | Acquired | 61 | Scott Anderson CEO & President | — | — |
| 13 | BookSeats.com Online personalized holiday packages booking platform | $1M | 33 mo ago | Seed | 3 | — | PHPLaravelNginx+33 | 1 partnership |
| 14 | SecondHome Online platform for booking vacation rentals | $600K | 163 mo ago | Deadpooled | — | Thomas Sampson Co-Founder | — | — |
| 15 | Sitata Online platform that provides location-based health & other emergency information for travelers | $120K | 90 mo ago | Seed | 20 | Mark Pavlides Advisor to Founder | BreakdanceWordPressMySQL+16 | — |
Top 12 Online Travel companies in Ontario
#1
Series A · Ottawa, Ontario · founded 2019 · 41 employees$76Mraised▾
Corporate cards and payment solutions for businesses. It provides payment and business accounts for businesses. Businesses can also issue virtual and physical corporate cards to manage, view and control their payments and spending.
- May 2025Venture Debt$3M
- May 2025Conventional Debt$50M
- May 2025Series A$23M
#2
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—
#3
Series A · Kitchener, Ontario · founded 2020 · 86 employees$34Mraised▾
Developer of an automated expense management platform designed to manage corporate cards, personal reimbursements, approvals, and invoices. The company's platform features virtual card generation for online spending, a spending tracker and controller, accounting automation, and periodic integrated reports and insights, enabling employees and managers to keep track of expenses and stay within the budget.
#4
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
#5
Seed · Brampton, Ontario · founded 2019 · 68 employees$4.4Mraised▾
App-based bus tickets booking platform. Travelers can check the availability of the tickets by providing the destination, date of traveling, number of passengers, and more. Bookings can be made through the app by providing an online payment. Their app is available for iOS and Android devices.
- Feb 2023Seed$1.2M
- 2022Seed—
- Nov 2021Seed$1.5M
- Aug 2021Seed$1.3M
#6
Seed · Ottawa, Ontario · founded 2016 · 87 employees$23Mraised▾
Online RV rental platform. Travelers can find RVs by providing the destination, pick-up & return date on the platform, as well as view the facilities available. Bookings can be made via the platform by making an online payment. RV owners can list their vehicles on the platform.
- May 2021Seed$20M
- 2019Seed$3M
- 2017Angel$150K
#7
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
#8
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
#9
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
#10
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
#11
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
#12
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
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.