Chekin vs Uplisting: Head-to-Head Comparison
TL;DR: Chekin and Uplisting both target short-term rental operators. Pick **[Chekin](/chekin-review/)** if: Operators in Spain (Registro de Viajeros / Parte de Viajeros), Italy (Alloggiati Web), Portugal (SEF/SEF.HOS), and France (taxe de séjour) who need automated police registration and tourist-tax reporting that would otherwise be manual, error-prone, and legally risky. Pick **[Uplisting](/uplisting-review/)** if: UK/EU operators in the 5-50 property band who want tight Airbnb/Booking.com/Vrbo syncing plus a direct-booking engine with security deposits and guest verification.
Category: Property Management Software · Chekin · Uplisting
At a glance
| Chekin | Uplisting | |
|---|---|---|
| Category | Guest registration and automated tax reporting for STRs in regulated European markets | All-in-one channel manager + direct-booking engine for small-to-mid STR operators |
| Founded | 2017 | 2018 |
| HQ | Valencia, Spain | London, United Kingdom |
| Pricing | from $4/mo | from $100/mo |
| Best for | Operators in Spain (Registro de Viajeros / Parte de Viajeros), Italy (Alloggiati Web), Portugal (SEF/SEF.HOS), and France (taxe de séjour) who need automated police registration and tourist-tax reporting that would otherwise be manual, error-prone, and legally risky. | UK/EU operators in the 5-50 property band who want tight Airbnb/Booking.com/Vrbo syncing plus a direct-booking engine with security deposits and guest verification. |
| Overall | 6.8/10 | 7.1/10 |
Feature-by-feature
| Feature | Chekin | Uplisting |
|---|---|---|
| Channel manager | — | ✅ Native |
| Unified inbox | — | ✅ Native |
| Direct booking site | ⚠️ Partial | ✅ Native |
| Task management | — | ✅ Native |
| AI guest messaging | — | ⚠️ Partial |
| AI that takes actions | ⚠️ Partial | — |
| Automation rules | ✅ Native | ✅ Native |
| Pricing optimizer | — | 🔌 Via integration |
| Open API | ✅ Native | ✅ Native |
| Mobile app | ✅ Native | ✅ Native |
| Multi-calendar | — | ✅ Native |
| Accounting / reporting | ⚠️ Partial | ⚠️ Partial |
| Revenue management | — | ⚠️ Partial |
Scores by dimension
| Dimension | Chekin | Uplisting |
|---|---|---|
| Ease of use | 7/10 | 8/10 🏆 |
| Features depth | 7/10 | 7/10 |
| Value for money | 8/10 🏆 | 7/10 |
| Support | 7/10 🏆 | 6/10 |
| AI capability | 5/10 | 5/10 |
| Scalability | 7/10 | 7/10 |
| Learning curve | 6/10 | 8/10 🏆 |
| Pricing transparency | 7/10 | 9/10 🏆 |
Where Chekin wins
- Chekin does not clearly out-score Uplisting on any dimension in this directory.
Where Uplisting wins
- Learning curve — 8/10 vs 6/10
- Pricing transparency — 9/10 vs 7/10
- Channel manager — native in Uplisting, not in Chekin
- Unified inbox — native in Uplisting, not in Chekin
- Task management — native in Uplisting, not in Chekin
- Multi-calendar — native in Uplisting, not in Chekin
Which one should you pick?
Pick Chekin if: Operators in Spain (Registro de Viajeros / Parte de Viajeros), Italy (Alloggiati Web), Portugal (SEF/SEF.HOS), and France (taxe de séjour) who need automated police registration and tourist-tax reporting that would otherwise be manual, error-prone, and legally risky. Pick Uplisting if: UK/EU operators in the 5-50 property band who want tight Airbnb/Booking.com/Vrbo syncing plus a direct-booking engine with security deposits and guest verification.
Pick by operator profile
| Profile | Winner | Why |
|---|---|---|
| Solo host (1-5 units) | Uplisting | Higher profile fit (7.3 vs 6.8). |
| Boutique operator (6-20 units) | Tie | Both score within a rounding error on this profile — pick on pricing and gut. |
| Professional PM (20+ units) | Chekin | Higher profile fit (7.3 vs 7.1). |
| Enterprise (100+ units) | Chekin | Higher profile fit (7.2 vs 7.0). |
| Multi-market operator | Tie | Both score within a rounding error on this profile — pick on pricing and gut. |
| Tech-forward, AI-first | Tie | Both score within a rounding error on this profile — pick on pricing and gut. |
| Budget-conscious | Uplisting | Higher profile fit (7.8 vs 7.4). |
Chekin in one paragraph
Chekin — Guest registration and automated tax reporting for STRs in regulated European markets. Strengths: Only guest-experience tool with deep, country-specific legal-registration coverage across Spain, Portugal, Italy, France, Germany, and more — a genuine regulatory moat; Automated filing to government portals (Registro de Viajeros, Alloggiati Web, SEF) replaces daily manual paperwork; Automated tourist-tax calculation, collection, and remittance by jurisdiction. Weaknesses: Narrow geographic sweet spot — value collapses outside regulated EU markets; Guest-experience layer (messaging, upsells) is thinner than Duve or Enso Connect — most operators pair Chekin with one of those. Full Chekin review →
Uplisting in one paragraph
Uplisting — All-in-one channel manager + direct-booking engine for small-to-mid STR operators. Strengths: Airbnb Preferred Plus partner status; Direct-booking engine with security-deposit collection and guest identity verification built in; eSign rental agreements native to the platform. Weaknesses: Entry price ($100/mo for up to 5 properties) is expensive for 1-2 property hosts; Email/chat support only — no phone; chat bot widely disliked. Full Uplisting review →
See also
- All Property Management Software comparisons
- 5stelle vs Chekin
- 5stelle vs Uplisting
- AirDNA vs Chekin
- AirDNA vs Uplisting
- Amenitiz vs Chekin
- Amenitiz vs Uplisting
FAQ
Is Chekin or Uplisting cheaper?
Chekin is cheaper at the entry level ($4/mo vs $100/mo).
Does Chekin have better AI than Uplisting?
Chekin and Uplisting score equally on ai capability (5/10).
Which is easier to use, Chekin or Uplisting?
Uplisting scores higher on ease of use — 8/10 vs 7/10.
Can I switch from Chekin to Uplisting?
Yes, but plan for migration cost: channel reconnections, template rebuilds, automation recreation, and team retraining. Both Chekin and Uplisting export reservation history; neither exports their automation rules cleanly. Run both in parallel for at least two weeks before cutting over.