Softwr

Scheduling · head to head

Calendly vs Uplisting

Calendly logo

Calendly

Scheduling

Scheduling automation platform for eliminating back-and-forth

From
Free
Rated
-
Full reviewWebsite
Uplisting logo

Uplisting

Travel

Short-term rental management with a flat per-property price and no percentage of revenue

From
$100/month
Rated
-
Full reviewWebsite

The short version

  • Only Calendly has a free tier, so it costs nothing to try first.
  • Each has a real cost: Calendly the free plan allows one event type and one calendar connection, so it cannot handle different meeting formats; Uplisting the 100 US dollar monthly minimum means an owner with one or two properties pays roughly fifty dollars per unit, five times the effective rate a twenty-unit manager pays.
  • They diverge on capability: Calendly covers Calendar sync, Uplisting covers Channel sync.
  • Prices and features above were last checked on 31 August 2026.

Where they differ

Only the attributes on which Calendly and Uplisting actually diverge.

Attributes where Calendly and Uplisting differ
AttributeCalendlyUplisting
Starting priceFree$100/month
Pricing modelUnknownPer property per month
Free tierYesNo
CategorySchedulingTravel
Founded2013Unknown

Identical on both: platforms (Web, iOS, Android), user rating (Not yet rated).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Calendly

  • Calendar sync
  • Automated scheduling
  • Custom availability
  • Time zone detection
  • Reminder emails
  • Buffer time
  • Meeting polls
  • Embed on website

Only in Uplisting

  • Channel sync
  • Direct booking site
  • Automated messaging
  • Cleaning and team management
  • Guest verification
  • Smart lock codes
  • Unified inbox
  • Multi-unit handling

What people use each for

The jobs each tool is most often brought in to do.

Calendly

  • Sales meetingsnot Uplisting
  • Interview schedulingnot Uplisting
  • Customer callsnot Uplisting
  • Office hoursnot Uplisting
  • Webinar registrationnot Uplisting

Uplisting

  • A manager with fifteen city apartments who wants fixed software cost rather than a percentage of high nightly ratesnot Calendly
  • An operator burned by double bookings across Airbnb and Booking.com wanting hard sync protectionnot Calendly
  • A team coordinating cleaners across same-day turnovers with automated task assignmentnot Calendly
  • A host issuing smart lock codes automatically instead of arranging key handoversnot Calendly

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Calendly

  • The free plan allows one event type and one calendar connection, so it cannot handle different meeting formats
  • Automated reminders and multiple calendars need Standard at $10 per seat per month
  • Round-robin routing, lead qualification and Salesforce integration require Teams at $16 per seat per month
  • SAML single sign-on, audit logs and domain control are Enterprise only, starting at $15,000 a year
  • Advertised prices are the annual rates

Uplisting

  • The 100 US dollar monthly minimum means an owner with one or two properties pays roughly fifty dollars per unit, five times the effective rate a twenty-unit manager pays.
  • Owner statements and trust accounting are effectively absent, so agencies that must report to and pay property owners need separate bookkeeping alongside it.
  • Payments are tied to Stripe for direct bookings, which limits operators in countries Stripe does not serve well or who want to keep an existing acquiring relationship.
  • Channel coverage is narrower than the larger platforms: Airbnb, Booking.com and Vrbo are solid but regional OTAs and wholesale distribution are not there.
  • Reporting is basic, with limited custom report building, so investors or multi-entity operators typically export data and analyse it elsewhere.

Pricing, plan by plan

Calendly

Free
  • FreeFree
    • 1 event type
    • 1 calendar connection
    • Basic confirmation email
  • Standard$10/month
    • Unlimited event types
    • Multiple calendars (up to 6)
    • Integrations with HubSpot, Mailchimp, Stripe, PayPal
  • Teams$16/month
    • All Standard features
    • Salesforce integration
    • Round-robin meetings
  • Enterprise$15000/year
    • All Teams features
    • Salesforce routing lookup
    • Microsoft Dynamics 365

Uplisting

$100/month
  • Pro$100/month
    • 100 USD monthly minimum
    • About 20 USD per property per month
    • Channel manager, direct booking site and automation included
  • Pro at scale (21 to 100 listings)$undefined/month
    • About 10 USD per additional listing beyond twenty
    • Same feature set
    • No revenue share
  • Pro above 100 listings$undefined/month
    • About 5 USD per additional listing beyond one hundred
    • Volume rate for larger portfolios
    • No revenue share

Which should you pick?

Choose Calendly if

  • You need calendar sync.
  • You want to start without paying.
  • You work on Web, iOS, Android.
  • You also want automated scheduling.
Calendly review

Choose Uplisting if

  • You need channel sync.
  • You work on Web, iOS, Android.
  • You also want direct booking site.
Uplisting review

Questions people ask

Is Calendly or Uplisting better?
Neither clearly leads. Calendly starts at Free and Uplisting at $100/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Calendly or Uplisting?
Calendly has a free tier; the other does not. Paid plans start at Free for Calendly and $100/month for Uplisting.
Does Calendly or Uplisting run on more platforms?
Both run on Web, iOS, Android, so platform support will not decide this one for you.
Can I use Calendly for free?
Yes. Calendly has a free tier, so you can try it without paying. Uplisting starts at $100/month.
What is Calendly best used for?
Calendly is most often used for sales meetings, interview scheduling, customer calls, office hours. Of those, sales meetings and interview scheduling are not what Uplisting is typically brought in for.
What can Calendly do that Uplisting cannot?
Calendly covers Calendar sync, Automated scheduling, Custom availability, Time zone detection. Uplisting covers Channel sync, Direct booking site, Automated messaging, Cleaning and team management.

Answered from the vendors’ own pages

Calendly: Does the free tier include automatic reminders?

No. The free plan only includes a basic confirmation email when someone books. Automated reminder workflows, SMS reminders, and follow-up sequences require the Standard plan ($10/month or higher).

Source
Uplisting: Does Uplisting take a percentage of bookings?

No. It charges a flat monthly rate per property and takes no cut of reservation value, including on direct bookings.

Calendly: Can I offer multiple meeting types on the free plan?

Only one event type can be active at a time. You can create multiple event types, but only one booking link works simultaneously. Switching between different meeting lengths requires manually activating another event type.

Source
Uplisting: What is the minimum I can spend?

One hundred US dollars a month, regardless of whether you have one property or five.

Calendly: Does Calendly work with Apple Calendar and iCloud?

No longer for new users. As of August 20, 2024, new users cannot connect iCloud or Apple Calendar. Existing connections continue to work, but Calendly ended support for new Apple Calendar integrations citing Apple's security changes.

Source
Uplisting: Does it do owner payouts and statements?

Not meaningfully. Managers who owe monthly statements to property owners generally run accounting separately or choose Hostaway or Guesty instead.

Calendly: What platforms can I use Calendly on?

Calendly is available on Web, iOS, and Android. Browser extensions are available for Safari. There are no dedicated Windows or Mac desktop applications.

Source
Uplisting: Which channels connect?

Airbnb, Booking.com and Vrbo are the core two-way connections, plus its own direct booking site and Google Vacation Rentals.

Calendly: What does the Standard plan ($10/month) add over free?

Unlimited event types, multiple calendar connections (up to 6), integrations with HubSpot, Mailchimp, Salesforce, Stripe, PayPal, Zapier, and webhooks, plus automated reminders and email sequences.

Source
Share

Related pages

More on Calendly

More on Uplisting

Keep looking

Other head to heads