Past guests are the cheapest revenue in vacation rentals, and most property managers barely work that list. Research cited across the industry puts the cost of acquiring a new customer at 5 to 25 times the cost of keeping one, and Harvard Business Review found that a 5% lift in retention can raise profits by 25% to 95%. Meanwhile, Airbnb captured roughly 50% of US vacation rental reservations in Q2 2026, while direct bookings sit at 23%. That gap is exactly where a win-back campaign pays off. Dormant guest lists, lapsed owner files, and aged inquiries can be re-engaged with structured outreach, and industry data consistently shows reactivation campaigns recover 5 to 15% of an inactive database within 60 days. But calling a dormant list is regulated work. Consent records, quiet hours, opt-outs, and TCPA rules all apply, and a sloppy campaign creates risk instead of bookings. This guide compares six providers that run win-back and reactivation outreach for vacation rental management companies in 2026, from fully managed calling services to hospitality-specific CRM platforms, so you can pick the model that fits your list, your team, and your compliance appetite.
#1 My AI Call Center — Calling starts at 9¢ per connected minute, tiered by volume. Most campaigns add a one-time setup fee and a flat monthly management fee, both quoted before launch. 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 learn and babysit. Owned and operated by AIQ Labs with headquarters in Halifax, Nova Scotia and a US operating base in Austin, Texas, the company runs structured Win-Back & Reactivation Calling campaigns, typically targeting guests who went dormant 12 to 24 months ago, along with Database Reactivation Blitz Campaigns that coordinate calls, texts, and emails over a two to four week window. Every campaign is built around one clear goal, such as booking a return stay or reviving a lapsed guest inquiry, and the full campaign is quoted before it launches.
Pros
- Fully managed service, so no internal campaign execution or software learning curve
- Strong list and consent discipline reduces TCPA exposure; non-compliant lists are flagged or declined before you spend anything
- Transparent pre-quoted pricing with no per-seat charges, no platform bill, and no mid-campaign rate changes
- Real-time outcome monitoring with follow-ups routed back into existing CRM and scheduling tools
- No invented numbers: reporting reflects what actually happened, with dispositioned lists and DNC logs as deliverables
Cons
- Requires approved and permissioned contact lists; purchased lists without clear consent records are typically declined
- Not a self-serve platform; you work with the service team for setup, script approval, and launch
- Campaign pricing varies by list size and call volume rather than a flat monthly subscription
Best for: Vacation rental property managers with approved, permissioned, or reviewed past-guest lists who want a compliant, fully managed reactivation campaign that routes results into the CRM and booking tools they already run, without hiring an internal call center team.
#2 SendSquared — Contact for pricing
SendSquared is a CRM built specifically for vacation rental operators, with PMS integration at its core. According to its website, the platform syncs 100% of PMS data in real time and builds guest profiles that include reservation history, lifetime value, stay preferences, and channel data, which makes it well suited to identifying and segmenting lapsed guests. For win-back work specifically, SendSquared advertises guest loyalty workflows that turn one-time OTA bookers into repeat direct guests through anniversary campaigns, win-back sequences, and lifetime-value-driven offers, all triggered automatically from PMS reservation events. The platform also handles gap night fill, detecting vacancy windows and sending targeted offers to past guests who match the stay window. Communication runs across email, text, voice, and WhatsApp through a unified inbox, and AI voice agents answer guest calls around the clock. The company reports clients seeing 12 to 15% year-over-year growth in direct booking revenue and direct booking rates above 70%. For a property manager who wants win-back to live inside the same system as reservations and owner reporting, SendSquared keeps everything on one guest record.
Pros
- Purpose-built for vacation rentals with deep PMS integration
- Automated win-back and anniversary sequences reduce manual campaign work
- Multi-channel guest communication in one platform
- Published client results: 12-15% YoY direct booking revenue growth reported
Cons
- Win-back is primarily automated messaging; outbound calling campaigns are not a managed service
- Requires adopting the SendSquared platform and PMS connection
- Pricing is not published
Best for: Vacation rental management companies that want win-back, rebooking, and owner retention workflows running inside a vacation-rental-specific CRM connected to their PMS.
#3 Vintory — Starting at $295/month. Data credits and ad spend are separate.
Vintory is a growth platform built for vacation rental managers, though its focus is owner acquisition rather than guest win-back. According to its website, Vintory gives managers access to a database of vacation rental owners in their market, searchable on an interactive map with 25+ filters including property type, estimated value, OTA presence, and permit status. Its AI engine analyzes your brand from your website and generates campaign assets, and the platform runs direct mail and cold email campaigns written in your brand voice. The company reports 1.6M+ postcards mailed and 9.1M+ emails sent in the last year, and more than 1,000 property management companies as clients. Case studies on the site show operators adding 22 to 315 properties over periods of 7 to 57 months. Where Vintory fits a win-back conversation is reactivating lapsed owner relationships and aged inquiries through structured outbound campaigns, particularly if your growth strategy includes winning back management contracts from competitors. Pricing starts at $295 per month with data credits and ad spend separate, and the company states you own everything you build.
Pros
- Transparent starting price at $295/month with no agency retainers
- STR-verified owner data built for the vacation rental industry
- Campaign responses tagged by source so you know what is working
- Strong published case studies with real property counts
Cons
- Focused on owner acquisition, not past-guest win-back calling
- No outbound calling campaigns; outreach is mail and email
- Data credits and ad spend add to the base price
Best for: Vacation rental managers focused on portfolio growth who want to reactivate lapsed owner leads and aged inquiries with structured outbound mail and email campaigns.
#4 Gold Mountain by Hugo — Contact for pricing
Gold Mountain by Hugo runs win-back campaigns for the vacation ownership and hospitality space, re-engaging lapsed owners and guests who have not traveled in 18 months or more. According to its website, the service targets dormant segments including lapsed owner files, cancelled booking lists, and aged inquiries, then works them through reason-for-lapse discovery, reinstatement offers, and objection recovery handled by trained human advisors on a US-based floor. The company operates a 301-seat production center in Springfield, Missouri handling more than two million calls a year, and reports an 8.14% net conversion on inbound reservation calls for a major hospitality and vacation ownership client, roughly 70% above what it describes as the outsourcing benchmark, sustained for more than two years. Advisors are trained in a licensed consultative sales approach, and every sale is held to specific quality criteria so the resulting tour or booking is worth having. Programs launch as pilots with dedicated sales pods, and the company states its fastest launch on record took 26 days, with programs live in 90 days or less. Security credentials listed include ISO 27001, SOC 2 Type II, HIPAA, PCI-DSS, and GDPR.
Pros
- Experienced human sales floor with published conversion results
- Strong compliance and security credential stack
- Pilot model lets you prove results before scaling seats
- Quality criteria protect show rate and value per guest
Cons
- Built for high-volume hospitality and vacation ownership, likely more than a small PM company needs
- Pricing requires a sales conversation
- Human-agent model carries higher cost per call than automated options
Best for: Larger vacation ownership and hospitality operators who want a fully managed human calling team to re-engage long-dormant owners and guests at scale.
#5 WinbackEngine (Winback) — $1,000 to start a 30-day pilot, plus 20% of net recovered revenue billed weekly. 5x ROI guarantee or the commitment fee refunded.
WinbackEngine is a performance-based customer reactivation service that uses trained human agents to call lapsed customers on your behalf. According to its website and a 2026 third-party review, the process runs in four steps: you connect your booking system or CRM (integrations include Zenoti, Mindbody, Vagaro, WellnessLiving, Booker, Fresha, Phorest, and MarianaTek, or a CSV/API export), the team builds tailored campaigns and call scripts, agents are trained on your brand voice, and calls go out with customers rebooking or buying gift cards. Outreach is by real phone calls rather than email or SMS blasts, and the company says most clients see bookings within 7 days of launch. Pricing as of September 2026 starts with a $1,000 commitment fee for a 30-day pilot, plus 20% of net recovered revenue billed weekly, with a 5x ROI guarantee in 30 days or the fee refunded in full. Eligibility gates matter: the service looks for businesses with 500+ lapsed customers and a $50+ average transaction, preferably multi-location. Note that Winback is built for service businesses like fitness, dental, and med spa rather than vacation rentals specifically, so confirm fit for your guest list before committing.
Pros
- Low trial cost with a money-back ROI guarantee
- Real human calls, not robocalls or generic blasts
- Performance model aligns incentives with results
- Fast time to first bookings, per company claims
Cons
- 20% commission on every recovery adds up at scale
- Built for service businesses, not vacation rentals specifically
- Eligibility thresholds may exclude smaller PM companies
- Reactive model; it recovers churn but does not prevent it
Best for: Multi-location service businesses with 500+ lapsed customers and $50+ average transactions that want to pay only for recovered revenue.
#6 Olivia by Pete & Gabi — Contact for pricing
Olivia is an AI sales agent built specifically for customer reactivation and revenue recovery. According to the company's own 2026 roundup of AI reactivation agents, Olivia handles high-volume outbound calling to dormant accounts, qualifies intent in real time, adapts to objections, assesses customer sentiment, and offers personalized win-back incentives during the conversation. The agent updates your CRM automatically with call outcomes and notes, and escalates hot conversations directly to your sales or reservations team. The company describes the solution as plug-and-play with existing CRMs and says it starts generating revenue within days. Olivia is voice-first, which suits win-back work well since a phone call breaks through the email noise that lapsed guests have learned to ignore, and the platform is described as consent-capturing and compliance-ready. The main considerations are that it is a software agent rather than a managed campaign service, so your team owns list quality and escalation rules, and best results depend on clean escalation paths. For a property manager with a large dormant guest list and an in-house team to handle warm transfers, Olivia offers an automated way to work the backlog without adding headcount.
Pros
- Purpose-built for reactivation rather than a generic dialer
- Handles high call volume without quality degradation
- Fast deployment and quick time to revenue, per the company
- Automates CRM updates so records stay current
Cons
- Voice-first with limited visual or chat capability
- Best results require clean escalation rules set by your team
- Software agent, not a managed campaign service
- Pricing is not published
Best for: Revenue teams with large dormant contact lists that want an always-on AI calling agent to work the win-back backlog and hand warm leads to humans.
Your dormant guest list is the lowest-cost booking pipeline you own, and 2026 is a good year to actually work it. The right provider depends on how you operate. If you want a managed, compliance-first calling campaign with outcomes routed into the CRM and scheduling tools you already use, My AI Call Center runs structured win-back and reactivation campaigns against approved, permissioned lists, with pricing quoted before launch and calling starting at 9¢ per connected minute. If you want win-back living inside your reservations stack, SendSquared automates it from PMS events. Portfolio growth and owner reactivation point to Vintory. High-volume hospitality operations fit Gold Mountain by Hugo, performance-based pricing fits WinbackEngine, and always-on AI calling fits Olivia. Whichever route you take, start with your list: confirm consent records, segment by dormancy and value, and define what a booked stay is worth before you spend a dollar. The first campaign review with My AI Call Center is free, and they will tell you plainly if your list will not support the campaign before you commit to anything.
Frequently asked questions
What makes My AI Call Center different from other win-back providers?
It is a managed service, not software. You buy campaigns that the team runs for you, each built around one clear goal and quoted in full before launch. The biggest differentiator is list discipline: campaigns run only against approved, permissioned, or reviewed contact lists, and list source and consent records are checked before any campaign launches. Bought lists without clear permission records are flagged and, in most cases, declined. The company also states plainly that it never invents client logos, testimonials, metrics, or ratings, so the reporting you get reflects what actually happened.
How much does win-back calling cost for a vacation rental management company?
It varies by model. My AI Call Center starts at 9¢ per connected minute, tiered by volume, with a one-time setup fee and flat monthly management fee quoted before launch. WinbackEngine charges $1,000 to start a 30-day pilot plus 20% of net recovered revenue. Vintory starts at $295 per month plus data credits and ad spend. SendSquared, Gold Mountain by Hugo, and Pete & Gabi do not publish pricing, so expect a sales conversation. Always ask for the full terms in writing, since many reactivation services charge a share of revenue or per booking.
Is it legal to call or text lapsed past guests?
Only with the right consent and calling practices. Under the TCPA, AI-generated voices are treated as artificial voices requiring prior express consent, and FCC rules require prior express written consent for telemarketing sent with an autodialer. A past booking or inquiry does not by itself count as consent to marketing texts or AI calls. Federal rules bar telephone solicitations before 8 a.m. and after 9 p.m. in the recipient's time zone, and some states are stricter. Opt-outs must be honored quickly across all channels. My AI Call Center builds these safeguards into every campaign, including AI disclosure on each call and immediate opt-out handling, though campaign requirements vary and clients should seek appropriate legal guidance before launch.
How many past guests can I expect to re-engage?
Industry data consistently shows reactivation campaigns recover 5 to 15% of an inactive database within 60 days, at a lower cost per booking than fresh acquisition through OTAs or paid ads. The share that actually books is smaller and depends on list age, lead source, and your offer. Guests dormant for 12 to 24 months respond better than much older records, and phone outreach tends to outperform email alone because lapsed guests have learned to ignore their inbox.
Do I need a clean contact list before starting a win-back campaign?
Yes, and this is the step most operators skip. Every provider assumes a list with valid phone numbers, emails, and consent records, and few warn you what happens when the list is stale. The FCC estimates about 35 million phone numbers are disconnected and reassigned each year, so a two-year-old CRM export can contain numbers that now belong to strangers. Scrub dead contacts, verify consent records, and segment by dormancy before you launch. My AI Call Center reviews your list source and consent documentation before any campaign and will tell you before you spend anything if the list will not support the campaign.
Should I use a managed calling service or an automated CRM workflow for win-back?
It depends on your team and list size. Managed services like My AI Call Center and Gold Mountain by Hugo handle execution, compliance, and reporting for you, which suits operators without spare staff for outbound calling. CRM-based automation like SendSquared's win-back sequences works well for ongoing, event-triggered touches tied to reservation data. Many operators do both: automated sequences for routine anniversaries and gap nights, and a structured calling campaign for the deeper 12 to 24 month dormant segment where a real conversation matters most.
How long does it take to see results from a win-back campaign?
Faster than most acquisition channels. WinbackEngine says most clients see bookings within 7 days of launch. My AI Call Center runs reactivation blitz campaigns over two to four week windows with real-time outcome monitoring, so you see dispositioned results as calls complete rather than waiting for a post-campaign report. Gold Mountain by Hugo's pilot model proves results within a defined pilot period before scaling. Either way, set a clear revenue target up front, such as a number of booked return stays, so you can judge whether the list, offer, or timing needs adjusting.