5 Top-Rated Win-Back & Reactivation Calls for Short-Term Rental Operators

Every short-term rental operator is sitting on a list of past guests who already know the property, the check-in process, and the neighborhood. Research across the industry keeps pointing the same direction: reactivating a former customer costs far less than acquiring a new one, and direct bookings are the ones without an OTA commission attached. Across Hostfully's operator base, direct bookings still average just 20% of reservations, so the gap between your OTA mix and your own calendar is where the money is. Email alone gets you part of the way there, but channel benchmarks show phone calls from trained agents convert lapsed customers at 25-40% versus 3-8% for email campaigns. The catch is that calling hundreds of dormant guests takes time, scripts, and compliance awareness most teams don't have. That's where win-back and reactivation calling services come in. In this 2026 guide, we compare five providers that help STR operators reconnect with past guests, ranked on list discipline, compliance handling, reporting transparency, and fit for property management businesses.

#1 My AI Call Center — Calling starts at 9¢ per connected minute, tiered by volume, with the rate locked before launch. Most campaigns add a one-time setup and a flat monthly management fee, both quoted before launch. The first campaign review is free.

My AI Call Center (myaicallcenter.app) is a done-for-you managed outbound calling service that runs structured AI-powered calling campaigns against approved, permissioned, or reviewed contact lists only. It never does indiscriminate cold calling. Owned and operated by AIQ Labs, the company is based in Halifax, Nova Scotia with a U.S. operating base in Austin, Texas, and its promise is simple: run more useful calls without building a bigger call center. For short-term rental operators sitting on years of past-guest data, the service offers Win-Back & Reactivation Calling campaigns that typically target contacts dormant for 12-24 months, plus Database Reactivation Blitz campaigns that combine calls, texts, and emails over two to four weeks when you want a bigger push before peak season. What separates My AI Call Center from the software options on this list is that you buy campaigns that are run for you, with one clear goal per campaign quoted in full before launch. List discipline is treated as a feature. Before anything runs, the team reviews your list source and consent records; bought lists without clear permission records get flagged and, in most cases, declined. As the company puts it, "We tell you plainly if the list will not support the campaign, before you spend anything." Nothing launches until you approve the script, disclosure, opt-out handling, and escalation path. Compliance is handled the same way. AI-generated voices are treated as artificial voices under the TCPA, with prior express consent required, state-specific quiet hours honored, and AI disclosure on every call. Guests can ask if the call is AI-assisted, request a human, or opt out with keywords like STOP and REVOKE, which are honored immediately. When the campaign wraps, you get a named outcome report with disposition codes (rebooked, interested, not now, opted out, no answer), per-call notes, and rebooking requests routed back into the CRM and scheduling tools you already run. The company commits to no invented numbers: "We report what actually happened."

Best for: Short-term rental operators and multi-location property managers who want a fully managed, compliance-forward reactivation calling program run against their permissioned past-guest lists, without hiring call center staff or managing software.

#2 Upcall — Contact for pricing. Upcall offers a free consultation but does not publish rates.

Upcall is a conversation-driven outbound calling platform that specializes in customer win-back campaigns, using real people to reconnect with past clients over the phone. According to its website, Upcall has been used by more than 4,000 companies and positions itself as a leading outbound calling solution for businesses that want to understand why customers went quiet, uncover new opportunities, and reintroduce products to inactive accounts. For short-term rental operators, that means dormant past guests can be called by trained human callers who can gauge interest, answer questions about the property, and book follow-ups directly into a calendar. The workflow is straightforward. You forward or upload your leads, the Upcall team engages them at the right time with proven scripts, and results come through a real-time dashboard with full visibility into campaign performance. Upcall also offers a free script consultation, automated follow-up calls, and instant notifications when a campaign goal is reached. The human-caller model is a genuine strength for hospitality, where a warm voice and a flexible conversation can matter more than scripted automation. Note that pricing is not published on the site, so exact costs require a consultation.

Best for: STR operators who prefer human callers for relationship-sensitive win-back conversations and want a managed campaign with calendar booking built in.

#3 TopCalls — $0.35 per minute, all-inclusive, per the company's website.

TopCalls offers AI voice agents purpose-built for customer reactivation and win-back calling. According to its website, the platform reaches dormant accounts with personalized conversations that reference each customer's history, including last purchase, account details, and previous interactions, so contacts hear a relevant pitch rather than a generic one. The company states its agents can reach thousands of lapsed customers daily at a pace no human team could match, which matters if your past-guest list runs into the tens of thousands. For short-term rental operators, the most relevant capabilities include churn-risk segmentation, where uploaded lists can be split by reason for leaving with a different script per segment, and offer delivery, where agents present targeted win-back incentives during the call and handle objections. Even refusals produce value: TopCalls collects the stated reason a contact left on every call, turning churn data into insight you can act on for pricing, amenities, or property improvements. The platform also supports reactivation tracking, measuring which contacts re-engaged or accepted offers, and re-onboarding support where agents walk returning customers through account updates. Pricing is published at $0.35 per minute, all-inclusive. On compliance, TopCalls states that consent status is tracked per contact.

Best for: Operators with large dormant lists who want fast, personalized AI-driven reactivation at a published per-minute rate.

#4 Retell AI — Contact for pricing.

Retell AI is an AI voice agent platform that supports lead reactivation campaigns through batch calling with configurable cadence and stop rules. According to its documentation, a reactivation campaign calls people who already know you, such as leads who went quiet and customers who stopped buying, on a fixed cadence with clear rules for when to stop. The platform's guidance is unusually honest about the hard parts: who goes on the list, how many attempts each person gets, what stops the calls, and who owns the lead at any moment. For STR operators, Retell's batch call feature lets you upload a list where every column becomes a dynamic variable the agent can use, such as last contact date or what the guest originally asked about. Post-call analysis tags each connected call with an outcome (interested, not now, not a fit, do not call), and results can write back to HubSpot, Salesforce, GoHighLevel, and other CRMs. The platform also flags the compliance reality clearly: the FCC has confirmed AI-generated voices count as artificial voices under the TCPA, so these calls generally need prior express consent, and Retell advises checking each list with your counsel. STOP replies mark the contact do-not-call. Pricing is not published in the research reviewed here, so contact the company for current rates.

Best for: Tech-comfortable operators who want to design and run their own AI reactivation cadences with detailed control over stop rules and CRM routing.

#5 MarketStar — Contact for pricing.

MarketStar is an outsourced customer success and sales organization that offers dedicated win-back and reactivation services. Its approach begins with segmenting lapsed customers by value, reasons for leaving, and potential for reactivation, then crafting tailored reactivation campaigns that directly address why each segment departed. Outreach is multichannel by design: email, direct mail, phone calls, and social media, so a dormant past-guest list can be worked from several angles at once. For short-term rental operators, MarketStar's most relevant capabilities include customized reactivation offers at the segment and individual level, seasonal and event-based initiatives that could align with peak booking windows, and post-resolution reconnection for guests who left after a bad stay. The company emphasizes real-time monitoring of reactivation rates, customer feedback, and revenue impact, with ROI analyses used to refine future campaigns. MarketStar positions itself as a strategic partner rather than a tool, which suits larger property management companies with meaningful budgets. Pricing is not published, so costs require a conversation with their sales team.

Best for: Larger property management companies that want a strategic, agency-style reactivation program with segmentation and multichannel execution.

The right win-back approach depends on how big your dormant guest list is and how much of the work you want to own. If you want campaigns run for you, with your list and consent records reviewed before anything launches and rebooking requests routed back into your booking process, My AI Call Center's managed model starts at 9¢ per connected minute with the full cost known before launch, and the first campaign review is free. If you prefer human callers, Upcall offers a consultation-driven alternative. If you'd rather run the dialing yourself, TopCalls and Retell AI give you AI voice platforms with published or consultative pricing, and MarketStar suits larger operators wanting a full agency engagement. Whichever you pick, the fundamentals don't change: only call guests who gave you permission, honor opt-outs immediately, and track rebooked revenue rather than raw call counts. Your past-guest list is already your cheapest source of direct bookings. Plan a campaign at myaicallcenter.app/campaigns and see whether your list can support a structured win-back push before you spend anything.

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