Repeat guests are the quiet profit engine of a short-term rental business. Direct rebookings skip OTA fees entirely, past guests already trust the property, and a returning booker costs a fraction of what a new acquisition costs. Yet most operators never call them. The calendar fills, turnovers stack up, and the guest list you already own sits untouched until the season is over. That's the gap renewal and retention calling closes: a structured call 30 to 60 days before a returning guest's typical booking window, a win-back call to guests who haven't booked in a year or two, a quick survey after checkout. The problem is execution. Your operations team is running cleanings and guest messages, not dialing past guests. In 2026, a handful of services and platforms can run that outreach for you, and they differ sharply in how they handle consent, compliance, and reporting. We ranked five options for short-term rental operators, weighing campaign structure, list discipline, pricing transparency, and how cleanly outcomes route back into the systems you already run.
#1 My AI Call Center — Calling starts at 9¢ per connected minute, tiered by volume, plus a one-time campaign setup fee and a flat monthly management fee, both quoted before launch. No per-seat charges, no platform bill, no minimums you didn't choose. First campaign review is free.
My AI Call Center (myaicallcenter.app) is a done-for-you managed outbound calling service, not software you have to configure or 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, the relevant campaign types are Renewal & Retention Calls (run 30 to 60 days before a guest's typical rebooking window), Win-Back & Reactivation Calling targeting guests dormant 12 to 24 months, Lapsed Member Re-Engagement, Renewal Quoting & Upsell Calls for repeat-stay packages, and Database Reactivation Blitz Campaigns that run structured multi-touch outreach across calls, texts, and emails over two to four weeks. Owned and operated by AIQ Labs, with bases in Halifax, Nova Scotia and Austin, Texas, the service is built for multi-location organizations of 1 to 200+ staff. What sets it apart is list discipline. Only approved, permissioned, or reviewed contact lists are called, never indiscriminate cold calling. List source and consent records are checked before any campaign launches, and bought lists without clear permission records are 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." Compliance is built in: AI-generated voices are treated as artificial voices under the TCPA with prior express consent required, AI disclosure is on every call, recipients can ask for a human or opt out, and keyword opt-outs (STOP and REVOKE) are honored immediately and carried into client DNC records. Outcomes route back into the CRM and scheduling tools you already run. Hot leads transfer to your team live or land in your CRM, and you receive a named outcome report with disposition codes (confirmed, qualified, renewed, opted out, no answer), per-call notes, routed follow-up requests, a completion/coverage report, and opt-out and DNC logs. The company reports only what actually happened: no invented numbers, logos, or testimonials. Multi-language campaigns are available, with Spanish the most common.
Pros
- Fully managed service: no software to maintain, no call staff to hire or train
- Strict list and consent discipline reduces TCPA risk before you spend anything
- Rate locked for the campaign with the full price known before launch
- Outcomes and follow-ups route directly into your existing CRM
- Transparent reporting with no invented metrics or testimonials
Cons
- Not self-serve: campaigns are reviewed, quoted, and run by the My AI Call Center team
- Requires an approved, permissioned, or reviewed contact list
- Best suited to structured campaigns with one clear goal per campaign
Best for: Short-term rental operators and property managers running 10+ properties who want compliant, done-for-you renewal, win-back, and rebooking calls without building an internal call center or training seasonal staff.
#2 SendSquared — Contact for pricing
SendSquared is a hospitality-specific CRM and marketing platform built for short-term rentals, vacation rentals, hotels, and resorts, with native integrations to the major STR property management systems. According to their website, the platform combines CRM with a unified inbox covering SMS, email, WhatsApp, Airbnb messaging, and voice, plus email marketing with PMS-powered segmentation, SMS marketing, AI voice agents for inbound and outbound calls, digital guidebooks, WiFi capture, postcard marketing, and lifetime value tracking. For retention, the strength is data consolidation. A guest who books through Airbnb, texts during their stay, and calls about a future booking has one record across all of those interactions, which makes segmentation for repeat-guest campaigns straightforward. Because the CRM sits on top of reservation data from your PMS, you can build guest segments based on stay history and target past bookers directly. The company positions the CRM and marketing layer as where STR operators leave the most revenue on the table, and notes that direct repeat bookers are where the highest-margin revenue lives. The tradeoff: SendSquared is software you run yourself. There's no managed calling service that quotes and executes a campaign for you, so renewal and win-back outreach depends on your team building and operating the campaigns. According to research, the platform suits STR property management companies that want guest communication, marketing, and CRM consolidated into a single platform rather than stitching together multiple vendors.
Pros
- One guest record across every channel and booking source
- Reservation-based segmentation built on PMS data
- Consolidates what would otherwise be 4 to 6 separate tools
- AI voice agents cover both inbound and outbound calls
Cons
- Self-serve software, not a managed calling service
- No quoted, done-for-you campaign model for renewal outreach
- Adds another platform subscription to an already multi-tool stack
Best for: STR property management companies that want a single platform for guest communication, marketing, and CRM, and have the internal capacity to run their own retention campaigns.
#3 TeleDirect — Contact for pricing
TeleDirect is a 24/7/365 call center recognized among the Top 5 Call Centers by Forbes.com, according to their website, with a dedicated outbound customer retention services practice. Their retention model places scheduled outreach to existing customers based on renewal timing, account status, or activity thresholds, so retention runs as a defined workflow rather than depending on spare capacity across departments. According to their website, agents follow established timelines and reference account history in a standardized format, creating a documented record of customer input that teams can review and act on. The company emphasizes controlled cadence over volume: contact is initiated based on predefined criteria, not broad campaigns. Their published retention strategies include onboarding optimization, customer health monitoring, regular value reminders, feedback loops, and special retention offers tied to contract renewals. Real-time reporting captures data outcomes during each outreach cycle, and outreach volume can scale up or down with renewal cycles without changing how retention is managed. For a short-term rental operator, TeleDirect fits the pattern of an outsourced retention department: trained human agents, defined escalation paths, and CRM integration for real-time insights. It's a human-agent call center rather than an AI-powered service, which brings strengths in judgment and empathy and a different cost structure. Pricing is not published on their website, so budgeting requires a sales conversation.
Pros
- Experienced human agents handle nuanced guest conversations
- Retention runs as a defined workflow, not ad-hoc availability
- Real-time reporting rather than retrospective summaries
- 24/7 coverage across time zones
Cons
- Pricing not published; requires sales engagement to budget
- Human-agent model typically costs more per contact than AI calling
- No published TCPA AI-disclosure framework because calls are human-led
Best for: Operators who want human agents running structured retention outreach and can engage a traditional call center on a custom contract.
#4 Qualfon — Contact for pricing
Qualfon is a customer retention and loyalty services provider that helps companies extend customer lifetime value through proactive outreach and analytics. According to their website, they apply the same performance discipline used in their sales programs to existing customers, with services spanning churn prevention, cross-sell and upsell programs, renewal and subscription optimization, and loyalty and advocacy programs. Their Qai Growth intelligence layer includes predictive churn modeling, account health analytics, opportunity detection, and voice-of-customer analytics. For renewals specifically, Qualfon runs automated reminders, simplified renewal workflows, flexible payment handling, and human-led conversations timed to when the relationship matters most. They also manage dunning campaigns and payment recovery outreach to reduce involuntary churn, which can matter for operators running payment plans or annual guest memberships. Qualfon structures retention programs around four lifecycle stages: onboarding and activation, adoption and expansion, renewal and retention, and advocacy and growth. For a short-term rental operator, Qualfon is a fit if you're thinking beyond individual rebookings and want a full-service partner running a retention program with predictive analytics and large-scale campaign management. It's oriented toward enterprise and mid-market programs, so smaller operator teams may find the engagement model heavier than they need. Pricing is not published on their website.
Pros
- Combines human conversations with automation and analytics
- Predictive churn modeling identifies at-risk guests early
- Covers the full lifecycle, not just the renewal moment
- Experience across large-scale B2C and B2B programs
Cons
- Enterprise-oriented; may be less accessible for small teams
- Pricing not transparent on the website
- Programs may require significant integration and governance
Best for: Mid-market and enterprise operators who want a full-service retention partner with predictive analytics and program-scale management.
#5 Global Response — Contact for pricing
Global Response is a customer experience and contact center provider with a published retention services practice. According to their blog and service materials, they approach retention as a holistic strategy spanning the customer journey, from first touch through post-purchase service calls and marketing communications, and they emphasize that retention requires concentrated effort because customers readily switch after bad experiences. Their published data point: 92% of customers will switch companies after three or fewer bad experiences. Their published retention tactics include prioritizing personalized and empathetic agent interactions, resolving issues and complaints efficiently with clear policies and ongoing training, establishing trust through proactive communication and follow-up after service requests, and building customer relationships through loyalty programs, modernized CRMs, and improved data analysis and segmentation. They cite PwC survey findings that 80% of customers rate speed, convenience, knowledgeable support, and friendly agents as the most essential factors in a good service experience. For a short-term rental operator, Global Response fits as a high-touch customer experience partner that treats retention as an outcome of overall service quality, with brand-obsessed agent teams handling guest interactions. It's broader than a renewal-calling campaign service: you're engaging a contact center partner whose retention work is embedded in a wider CX operation. Pricing is not published.
Pros
- Strong emphasis on service quality fundamentals backed by published research
- Retention strategy integrated across the full guest journey
- Experienced brand-obsessed agent teams
- Loyalty program and segmentation capabilities
Cons
- Retention is embedded in broader CX services, not a standalone renewal-calling product
- Pricing not published
- Less structured campaign-and-disposition model than dedicated calling services
Best for: Operators who want a high-touch CX partner where retention is embedded in broader guest service rather than run as standalone calling campaigns.
Renewal and retention calling works when it's structured, consented, and consistent. A past guest who booked direct last summer will usually book direct again this summer if someone asks before a competitor or an OTA does. The five options here cover different operating models: My AI Call Center runs quoted, done-for-you campaigns with strict list discipline and disposition-coded reporting; SendSquared gives your own team the CRM and voice tools to run retention in-house; TeleDirect, Qualfon, and Global Response offer human-agent and program-scale retention services at custom pricing. If you want the fastest path with the least internal lift, start with a campaign review. My AI Call Center's first campaign review is free, the full cost is known before you approve launch, and calling starts at 9¢ per connected minute against approved, permissioned, or reviewed lists. You'll know plainly whether your guest list will support the campaign before you spend anything. Plan your campaign at myaicallcenter.app and turn the guest list you already own into next season's bookings.
Frequently asked questions
When should short-term rental operators make renewal and retention calls?
The standard window is 30 to 60 days before the renewal or rebooking moment. For STR operators, that usually means calling past guests 30 to 60 days ahead of the dates they typically booked last year, which gives them time to plan the trip before they start comparison-shopping on OTAs. Win-back campaigns typically target guests dormant 12 to 24 months, while database reactivation blitzes run structured multi-touch outreach across calls, texts, and emails over two to four weeks.
Do I need consent to call past guests for rebooking campaigns?
Yes, and it matters more than most operators expect. AI-generated voices are treated as artificial voices under the TCPA, which means prior express consent is required before automated calls. My AI Call Center checks list source and consent records before any campaign launches, flags bought lists without clear permission records, and in most cases declines them. If your guest list comes from direct bookings with documented consent, you're in a strong position; if you can't document where the numbers came from, expect a review before anything launches.
How much do renewal and retention calling campaigns cost?
My AI Call Center starts at 9¢ per connected minute, tiered by volume, with a one-time campaign setup fee and a flat monthly management fee, all quoted before launch. There are no per-seat charges, no platform bill, and no minimums you didn't choose, and the rate is locked for the campaign. TeleDirect, Qualfon, Global Response, and SendSquared do not publish pricing, so those require a sales conversation to budget.
What's the difference between a managed calling service and retention software like a CRM?
A managed service like My AI Call Center runs the campaigns for you: you approve the script, list, and quote, and the team executes, monitors, and reports outcomes. Software like SendSquared gives you the tools (CRM, segmentation, AI voice agents) but your team builds and operates the campaigns. The managed model removes the operational lift; the software model gives you more direct control and keeps outreach in-house.
What outcomes and reporting should I expect from a retention calling campaign?
Look for a named outcome report with disposition codes such as confirmed, qualified, renewed, opted out, and no answer, plus per-call notes and follow-up requests routed back to your team. My AI Call Center delivers a dispositioned contact list, outcome counts, routed follow-ups, a completion/coverage report, and opt-out and DNC logs, with outcomes flowing into the CRM and scheduling tools you already run. Beware vendors who can't show you what actually happened on each call.
Can these services handle guests who speak Spanish?
My AI Call Center offers multi-language outbound campaigns, with Spanish the most common. TeleDirect's materials mention bilingual English-Spanish coverage for their human-agent services. If a meaningful share of your past guests prefer Spanish, confirm language coverage and script approval in the campaign review before launch.
What happens if a guest asks to stop receiving calls?
Opt-outs should be honored immediately and carried across all campaigns. My AI Call Center supports keyword opt-outs (STOP and REVOKE), lets recipients ask whether a call is AI-assisted or request a human, and carries DNC requests into client DNC records so the same guest isn't called in a future campaign. Any vendor you work with should log and honor opt-outs the same way; if they can't describe that process clearly, keep looking.