Fifteen years managing holiday home communities. Now on two continents.
Tripvillas started in Singapore in 2010 as a holiday home rental marketplace. Everything since — software, community management, exchange, hotels, and now North America — came from solving the problems our owners and communities actually had.
The story in five chapters
2010 — The marketplace
Founded in Singapore to connect travelers with family-owned holiday homes, with instant booking and dedicated support for holiday communities.
2014 — The systems
The distribution and operations platform our communities run on: one dashboard, 100+ booking channels.
2020 — The operator
Riritana Hospitality launched to manage whole communities on the ground — today over 1,000 completed homes, 2,000 in development.
The brands
Riritana for Asia, The Edmund for North America, and Tripvillas for communities that already have a name — three brands over one operating standard.
Today — North America
The same playbook, now offered to developers and HOAs in the United States and Canada from our Toronto office.
Roshan DSilva
Roshan founded Tripvillas in 2010 and remains its majority owner — the management team, not outside shareholders, controls the company. That ownership shows in how the group operates: long contracts, selective signings, and accountability to homeowners measured in yield, not press releases.
He has spent fifteen years in the holiday home industry across every seat — marketplace operator, software builder, developer partner and on-the-ground hospitality manager — and personally hosts at the group’s properties.
Tripvillas is passionate about what holiday homes mean to families: more space, more time together, and an asset that pays for itself.