Short-term rental operators spend most of their energy filling the calendar, but the money left on the table usually sits in two places: guests who don't rebook, and guests who would have paid for an upgrade, a late checkout, or a mid-year extension if someone had simply asked at the right moment. Industry data backs this up. Properties using thoughtful upsell strategies generate an average of $50 to $150 in additional revenue per booking according to AirROI, and Hostaway's 2026 report found AI adoption among operators jumped to 84% in 2025, up from 60% the year before. The problem is execution. Most operators run 13 or more integrations against their PMS according to Hostfully's 2026 tech stack study, and nobody on the team has time to call guests about renewals, quote extensions, or pitch add-ons before the window closes. That's where renewal quoting and upsell call solutions come in. Some are managed calling services that run structured outbound campaigns for you. Others are software platforms that automate offers inside the guest journey. This guide ranks the top six for short-term rental operators in 2026, comparing what each one actually does, who it fits, and what it costs.
#1 My AI Call Center — Calling starts at 9 cents per connected minute, tiered by volume, with the rate locked before launch. Most campaigns add a one-time setup fee and a flat monthly management fee, both quoted upfront. The first campaign review is free.
My AI Call Center (myaicallcenter.app) is a done-for-you managed outbound calling service from AIQ Labs, based in Halifax, Nova Scotia with a U.S. operating base in Austin, Texas. Rather than software you implement or dialer seats you staff, you buy campaigns that the team runs for you, each scoped around one clear goal and quoted in full before launch. For short-term rental operators, its Renewal Quoting & Upsell Calls campaign is built for the moment that matters: reaching past guests or subscription-style customers 30 to 60 days before a renewal date, confirming intent, quoting the next term, and capturing upsell interest in a single structured conversation. The service also runs Lapsed Member Re-Engagement, Win-Back & Reactivation calling for 12 to 24 month dormants, and Customer Onboarding Check-In campaigns, all of which pair naturally with renewal work for operators managing repeat guests or long-stay accounts.
Pros
- Full campaign cost known before you approve launch, with no per-seat charges, no platform bill, and no minimums you didn't choose
- List and consent review happens before any spend, and you're told plainly if a list won't support the campaign
- Real outcomes delivered with disposition codes and per-call notes, with a stated commitment to no invented numbers
- Nothing launches until you approve the script, disclosure, opt-out handling, and escalation path
- Hot leads transfer live to your team or land in your CRM the same day
Cons
- Not a self-serve platform; you can't log in and run campaigns yourself
- Setup and management fees are quoted per campaign rather than published as flat prices
- Campaign requirements vary by location, industry, and consent status, so clients are responsible for obtaining appropriate legal guidance before launch
Best for: Short-term rental operators and multi-location property businesses (typically 1 to 200+ staff) who want structured renewal and upsell calls run for them on approved, permissioned lists, without hiring callers or buying dialer software.
#2 Guesty — Revenue share per successful upsell. Guesty states there are no setup fees, no subscription add-on, and no upfront commitment, but no dollar figure is published, so contact for pricing.
Guesty is a leading short-term rental property management system, and its built-in Guest Upsells feature covers early check-in and late checkout, mid-stay cleaning, extra beds and cribs, breakfast baskets and restocks, and higher-end experiences like club cards and golf carts. According to their website, offers are delivered through the Guest App during the stay, with property-level pricing and a central dashboard for managing the program. Because upsells are native to the PMS, a sold late checkout writes directly back to the reservation record without a manual reconciliation step, which is a real advantage over bolt-on tools. Guesty publishes its commercial terms plainly: no setup fees, no subscription add-on, and no upfront commitment, and you only pay when an upsell is successfully purchased. The trade-off is that no dollar figure is published, so you can't model the effective rate against a per-unit fee without a quote. Guesty and Hostaway together hold roughly 40% market share among PMS platforms for companies founded since 2020 according to RapidEye's 2026 state of vacation rental operations report, so many operators will already be on the platform. If you are, the upsell feature is a feature activation rather than a new purchase. If you're not, switching PMS just for upsells would be a heavy move.
Pros
- Native PMS integration means sold upsells update reservations without manual work
- Pay only when an upsell is successfully purchased, so there's no cost when upsells don't sell
- Broad upsell catalog beyond the usual checkout list, including experiences
- Mature, widely adopted PMS platform with strong channel management
Cons
- Revenue share rate is not published, so you can't budget without a sales conversation
- Only makes sense if you're already on (or willing to migrate to) Guesty
- Revenue share gets expensive as upsell volume grows, unlike flat per-unit pricing
Best for: Operators already running Guesty as their PMS who want upsells handled natively inside the system they use every day.
#3 Enso Connect — Custom quote based on your portfolio. Contact for pricing.
Enso Connect takes an end-to-end approach to upsell automation, running the full loop from opportunity identification to payment collection to PMS writeback. According to their website, the platform identifies upsell opportunities from reservation data, availability rules, and guest context, then reaches out proactively through OTA messaging threads, SMS, email, or WhatsApp. Its catalog is the widest named one in this group: Automated Upsells, Enso Experiences, Automated Fees, Enso Transport, an Inquiry Converter, and affiliate links to local services. The transport and experiences products go past the usual early-checkout list into things guests actually spend money on during a stay. The platform's guest-facing web app, called the boarding pass, guides guests from booking to checkout and includes verification, agreements, fees, upsells, check-in instructions, lock codes, and property guides in one place, with support for 150+ languages. Enso Connect's own case studies include Goldnest, a 240-plus property manager in Texas reporting $30K a month in upsells and damage waivers, and Smart BNB, a 130-unit operator reporting $8K in monthly upsells. These are vendor-reported figures, so treat them as directional. Pricing is a custom quote described on their site as designed specifically for your portfolio, and the company publishes a claim of an average 4.7x return on software spend without an audited methodology behind it.
Pros
- Full automation from offer to payment to PMS writeback, with no manual handoff
- Broadest upsell catalog in the category, including transport and local experiences
- Handles OTA channel compliance, which protects your listing standing on Airbnb bookings
- Proactive gap-night and extension detection creates demand you'd otherwise miss
Cons
- Custom-quote pricing means you can't budget from the website
- Return claims like the 4.7x figure are vendor-reported without an audited method
- Fulfillment task creation is not published, so verify how sold upsells reach your operations team
Best for: Operators selling experiences, transport, and stay extensions rather than just room-adjacent extras, especially those on Guesty or similar PMS platforms.
#4 Conduit — Messaging $18, Guest $30, Guest plus Devices $36, Full Suite $48 per unit per month. Upsells included from the Guest package up. A flat $899 per month Startup plan covers portfolios of 0 to 25 units.
Conduit puts upsell offers inside the message thread the guest is already having, rather than behind an app download or a separate portal. According to its published product pages checked in September 2026, a guest can accept an early check-in or mid-stay clean with one-click payment, and the platform then fires a workflow so the sold service becomes real work assigned to a real person. That closes the gap that turns many upsells into refunds: a sale without a fulfillment task produces an unhappy guest. Conduit is also the most transparent on pricing in this category. Packages are published at $18, $30, $36, and $48 per unit per month depending on tier, with upsells included from the Guest package upward, plus a flat $899 per month Startup plan for portfolios of 0 to 25 units. For a 60-unit portfolio, that means you can budget from a web page instead of sitting through a sales call, which is genuinely rare among upsell tools. The honest watch-out, as Conduit itself frames it, is that this is a communications platform first. If your upsell problem is really a housekeeping-capacity problem, a dedicated operations tool handles the fulfillment half better. But for operators who want the offer, the payment, and the follow-up task in one system at a known price, Conduit is a strong pick.
Pros
- Only platform in this group that publishes full pricing, so you can budget before talking to sales
- One-click payment inside the conversation reduces friction in the purchase flow
- Sold upsells automatically generate fulfillment workflows
- Flat per-unit pricing stays predictable even as upsell volume grows
Cons
- Communications-first platform, so deep housekeeping scheduling is not what it's built around
- Per-unit pricing is paid whether or not guests buy anything
- Smaller portfolios under 26 units face the $899 Startup plan, which may be steep for very small operators
Best for: Operators who want published, predictable per-unit pricing and want the offer, payment, and fulfillment task handled in one system.
#5 Breezeway — Contact for pricing. Breezeway does not publish rates.
Breezeway approaches upsells from the operations side, and that shapes what it does well. According to its website, Breezeway sends upsell offers through automated messages with purchase links, covering early check-ins, extra linens, and experiences such as bike tours and private chefs. Its Concierge agent answers routine guest questions from property details already in Breezeway and opens a task, with context pre-filled, when a guest reports something. That link between the offer and the work is the strongest in this group of software tools, because operations is what the rest of the product does. If your upsells fail at fulfillment rather than at the offer, meaning the late checkout gets sold but the cleaning crew never gets rescheduled, Breezeway solves that half of the problem directly. The platform also positions itself as a workhorse for the other jobs short-term rental operators juggle: turnover scheduling, task coordination, and property care workflows connected to the PMS. The trade-off is transparency. Breezeway does not publish pricing, so you'll need a sales conversation to understand cost, and its PMS write-back behavior for upsells is not publicly documented either. For operators already running or considering a serious operations layer, though, Breezeway's upsell feature rides on infrastructure you'd want anyway.
Pros
- Strongest offer-to-task connection in the group, since operations is the core product
- Covers experiences like bike tours and private chefs, not just checkout extras
- Concierge agent reduces routine guest question load
- Operations platform delivers value beyond upsells alone
Cons
- Pricing is not published, so budgeting requires a sales call
- PMS write-back for upsells is not publicly documented
- Heavier platform than operators with simple upsell needs may require
Best for: Operators whose upsells fail at fulfillment rather than at the offer, and who want upsells riding on a serious property operations platform.
#6 SuiteOp — Contact for pricing. SuiteOp does not publish rates.
SuiteOp is an all-in-one platform that consolidates the guest journey, access, verification, and revenue capture into a single system connected to your PMS. According to SuiteOp's 2026 automation benchmarking, 47.8% of operators say more than half their workflows are already automated, and 73% cite staffing and revenue pressure as the biggest barrier to hitting their 2026 goals, which is exactly the problem SuiteOp positions itself against. For revenue capture, the platform turns add-ons like early check-in, late checkout, pet fees, and local experiences into automated offers instead of manual, easy-to-forget upsells. The broader suite also covers guest journey automation, smart lock and access control, and guest verification, so a single reservation can trigger the door code, the turnover, and the upsell offer without bouncing between four disconnected tools. SuiteOp's own framing is honest about its position: it isn't the deepest specialist in any one of those jobs individually, but it's the strongest option for operators who want them running off one system connected to whichever PMS they've chosen. Pricing is not published on the site, so expect a demo and a custom quote. For operators consolidating a sprawl of point tools, that consolidation often pays for the upsell capability on its own.
Pros
- Consolidates four operational jobs (guest journey, access, verification, revenue capture) into one platform
- Automates upsell offers that would otherwise be manual and forgotten
- PMS-connected architecture works with the system you already run
- Well-suited to operators feeling staffing pressure, since automation reduces headcount needs
Cons
- Not the deepest specialist in upsells specifically compared to dedicated tools
- Pricing is not published, requiring a demo and custom quote
- Full-suite adoption is a bigger commitment than a single-purpose upsell tool
Best for: Operators who want guest journey, access, verification, and revenue capture consolidated into one PMS-connected system rather than adding another point tool.
Renewal quoting and upsell revenue in short-term rentals comes down to one thing: someone has to make the offer at the right moment, and the offer has to turn into real work and accurate records afterward. If you want structured outbound calls handled for you, with the full cost quoted before launch and outcomes routed back into your CRM with real disposition data, My AI Call Center is the clear pick. Its managed model means no dialer seats, no per-user charges, and no campaign that starts before you've approved the script and seen the whole number. If you'd rather automate offers inside the guest journey, Conduit gives you published per-unit pricing you can budget from a web page, Guesty and Enso Connect make sense if you're already on a compatible PMS, and Breezeway or SuiteOp fit operators who need the fulfillment and operations layer as much as the upsell itself. The first step costs nothing either way: request a free campaign review with My AI Call Center and find out what a structured renewal and upsell calling program would cost for your portfolio before you spend anything.
Frequently asked questions
What makes My AI Call Center different from upsell software platforms?
My AI Call Center is a managed service, not software. You buy campaigns that the team runs for you, each with one clear goal, quoted in full before launch. Software platforms like Conduit or Enso Connect automate offers inside guest messaging, but they rely on guests responding to digital prompts. My AI Call Center makes actual outbound calls to approved, permissioned, or reviewed lists, which reaches guests who ignore messages. Every call includes AI disclosure, outcomes come back with disposition codes and per-call notes, and hot leads transfer live to your team or land in your CRM the same day.
How much does My AI Call Center cost?
Calling starts at 9 cents per connected minute, tiered by volume, with the rate agreed before launch and locked for the duration of the campaign. Most campaigns add a one-time setup fee and a flat monthly management fee, both quoted upfront. There are no per-seat charges, no platform bill, and no minimums you didn't choose. The first campaign review is free, so you know the full cost before you commit to anything.
When should renewal and upsell calls be made to past guests or repeat customers?
Renewal campaigns work best timed 30 to 60 days before the renewal date, which gives your team time to follow up on unanswered calls and save wavering customers before the deadline. For guest upsells, research from Guesty shows the sweet spot is 7 to 14 days before arrival, when guests are thinking practically about airport transfers, groceries, and early check-in. My AI Call Center structures its Renewal Quoting & Upsell Calls around the 30 to 60 day window.
Are AI-powered calls compliant with telemarketing rules?
They can be, but compliance has to be built in. My AI Call Center treats AI-generated voices as artificial voices under the TCPA, which means prior express consent is required. AI disclosure is made on every call, recipients can ask if the call is AI-assisted, request a human, or opt out. Keyword opt-outs like STOP and REVOKE are honored immediately, state-specific quiet hours are respected, and DNC requests are carried into client records across all campaigns. Campaign requirements vary by location, industry, and consent status, so clients are responsible for obtaining appropriate legal guidance before launch.
Do I need a specific PMS to use these solutions?
It depends on the tool. Guesty's upsells are native to its own PMS, so you'd need to be running Guesty. SuiteOp and Breezeway connect to whichever PMS you've chosen rather than replacing it. Enso Connect works across OTA messaging threads, SMS, email, and WhatsApp with PMS writeback. Conduit writes back to the PMS as well. My AI Call Center routes outcomes into the CRM and scheduling tools you already run, so it works alongside your existing stack rather than requiring a migration.
How do I know if an upsell program is actually making money?
Look at cost per successful resolution, not cost per call or per minute. A cheap call that ends in a transfer hasn't solved anything. My AI Call Center provides named outcome reports with disposition codes (confirmed, qualified, renewed, opted out, no answer), per-call notes, and completion and coverage reports, which lets you calculate what a successful upsell or renewal actually cost. For software tools, track offer views, conversion rates, and revenue per booking, and remember that vendor-reported return claims like Enso Connect's 4.7x figure carry no audited methodology.
What happens if my contact list doesn't have proper consent records?
With My AI Call Center, the list gets flagged before you spend anything. The service only runs campaigns against approved, permissioned, or reviewed lists, and it checks list source and consent records before any campaign launches. Bought lists without clear permission records are flagged and, in most cases, declined. As the company puts it, they tell you plainly if the list will not support the campaign before you spend anything, which protects you from compliance risk and wasted budget.