OnSeason (ex. Flataway)
“Can vacation rental managers escape OTA commissions by owning AI-discoverable direct-booking channels?”
Founded2023
HQSofia, Bulgaria
FoundersBoris Pavlov, Teodor Todorov
Total raised$534.3K
Latest roundPre-Seed, 2023
IndustryVertical SaaS / Hospitality
The story
Founded in 2023 as Flataway by former operators of one of Europe's largest short-term rental management companies. The team first built Calry, a unified PMS API, then pivoted to a broader hospitality direct-booking platform rebranded as OnSeason. The current thesis is that AI travel agents (ChatGPT, Claude) will disintermediate OTAs, and property managers need AI-discoverable direct-booking websites to capture that shift. Payments are outsourced entirely to Stripe — the company is a SaaS layer, not an embedded finance player.
Last 12 months
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Product timeline
2023
FlatAway Ltd. founded in Sofia, Bulgaria; raised pre-seed led by Eleven Ventures· founding
2024
Built Calry, a unified PMS API connecting 40+ property management systems· product
2025
Rebranded from Flataway to OnSeason; launched AI website builder (Staycy), zero-commission booking engine, and distribution network· pivot
2026
Positioned as AI-discoverable direct booking platform (ChatGPT, Claude, AI travel agents)· product
The stack
1 layer disclosed in OnSeason (ex. Flataway)’s embedded-finance stack
Payments / PSP
Accounting gap: none