Besty AI VS Enso Connect: STR Tools Comparison in 2025

If you’re a hospitality operator, looking to unlock scale with AI-powered tools for guest messaging and upsell revenue automation, you’re considering two options: Enso Connect and Besty AI. Here’s the short answer:

Enso Connect is best for short-term rental operators with 10+ listings who want high-quality AI and automation tools and a branded guest app with an e-commerce-level level intuitive upsell storefront. It’s ideal if you're looking to bring efficiency while scaling high-quality hospitality and boosting revenue.

Besty AI is a plug-and-play AI assistant that automates guest messaging and sells upsells, such as late check-outs and gap nights. It’s fast to set up and light on features and support.

For Airbnb hosts, one thing to note is that Besty AI is not an official Airbnb partner, while Enso Connect is a listed Airbnb partner.

Besty AI vs Enso Connect: Platform Overview

Enso Connect: AI-First Guest Experience that Pays for Itself

Enso Connect is an AI-native guest experience platform for short-term rental professionals, designed to boost revenue, efficiency and 5-star reviews. The platform integrates multiple touchpoints throughout the guest journey into a cohesive system, streamlining the experience for guests and hosts. Its mobile-optimized guest app consolidates check-in, guest verification, guidebooks, and upsells into a single powerful tool. Enso's AI-powered unified inbox is  

Key Features:
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• Agentic AI-powered unified inbox with multi-channel messaging for faster response times

• Digital guest portal (web app called the Boarding Pass) with Apple Wallet and Apple Pay integration 

• Automation workflows with conditional logic to enhance operational efficiency

• Smart devices integration, including automated access codes

• Custom upsells, fees, and a local experiences marketplace for incremental revenue and guest satisfaction

• Guest verification and security deposits with direct integration to security vendors

• Digital guidebooks to reduce phone calls and streamline operations

• CRM and guest database for target marketing

Service includes an onboarding and support team that provides dedicated hands-on help. The platform provides an intelligence dashboard to track guest management KPIs, like response times, revenue per stay and AI performance. 

Besty AI: The AI Messaging and Revenue Optimizer

Besty AI launched as an AI chatbot solution focused on automating guest communication for Airbnb, VRBO, and Booking.com. The platform has evolved to include AI-driven upselling tools, emphasizing reducing message response burden for hosts while capturing revenue opportunities.

Key Features:

• AI-powered guest messaging (autopilot or draft mode) with faster response times

• Gap night, Early check-in/late checkout upselling automation 

• AI task generation from reviews and conversations to streamline operations

• Direct booking website widget for rental managers

• Guest sentiment analysis for hospitality business optimization

• Conversation summaries to reduce manual review time

The platform positions itself as available today with quick deployment, allowing property owners to start benefiting from AI features within minutes. 

AI Technology: Comparing AI-Driven Tools Approaches

Enso Connect's Multi-Agentic AI Architecture

EnsoAI operates with what Enso describes as a multi-component system of AI agents:

• CoPilot mode drafts responses for human interaction and approval

• AutoPilot mode sends approved responses automatically based on confidence levels

• Smart handoff to a human when the confidence is under a set threshold 

• Contextual learning from approved edits in both sandbox and live inbox, categorized data from property management systems, guidebooks, SOPs, and real-time guest status from the Boarding Pass guest app

• Transparent reasoning by showing the thinking steps and sources behind each response

• Sentiment analysis detects guest emotions and conversation urgency to improve operational efficiency

• Testing AI automation in a safe environment (sandbox) that is also training the AI

• Adjusting to your brand's tone of voice and setting specific categories, times and days when messaging can be set on autopilot.

The platform emphasizes human interaction alongside AI tools, where AI agents assist rather than fully replace communication teams. EnsoAI handles complex queries effectively, delegating them to humans when it is not confident. It is a self-learning AI system that does not burden human teams with the constant task of updating AI content and teaching the system. 

Besty AI's Approach

Besty AI employs large language models (LLMs) trained on vacation rental conversations:

• Learning System: Analyzes past conversations and property listing data to match your communication style

• Confidence Scoring: Notifies rental managers when unsure about responses

• Smart Notifications: Alerts humans when intervention involving sensitive information is needed

• Host Notes Feature: Allows manual training with supplemental information

• Draft Mode: All responses can be reviewed before sending to maintain quality standards

Multiple user reviews report occasional inaccuracies in AI responses that require monitoring. LinkedIn discussions among short-term rental professionals note that application performance improves significantly after the initial training period.

Key Difference in Enso Connect's and Besty's AI Features

AI is at the core of Enso Connect's platform, and the guest journey aspect feeds into EnsoAI with real-time context unavailable to other AI messaging tools. Besty AI started as an AI-first company; however, it is shifting its focus to other aspects of property management, while alternatives continue advancing their AI capabilities.

Upselling and Revenue Features for Vacation Rentals

Enso Connect Upsells

Enso's upsell system, with its multi-agentic AI system, integrates directly into the Boarding Pass guest app:

• Custom upsells (early check-in, late checkout, amenities, services) for boutique hotels and vacation rentals

• Local experiences marketplace with affiliate revenue to enhance guest satisfaction and drive incremental revenue

• Conditional offers based on guest data 

• Stripe and Apple Pay integration for instant payment processing (no manual payment link request needed)

• 5% commission on upsell revenue 

• Damage waivers with 7% guest-paid fee

According to statistical data from Enso Connect customers, the platform's upsell revenue often covers the subscription cost, helping operators track return on investment. The system's manual configuration is streamlined by best practices templates and support from a dedicated onboarding team, and offers greater customization for each property listing. Enso Connect provides all users with an ROI Guarantee program: if users don't generate enough incremental revenue to cover their subscription cost, they receive continued service at no charge.

Besty AI Upsells

Besty's upselling focuses on automation and calendar intelligence through AI-driven tools:

• Automated gap night offers with a dynamic pricing model based on occupancy

• Automatic early check-in pricing for Airbnb, VRBO, and Booking reservations

• Automatic approval/denial based on same-day turnover rules from property management systems

• Proactive outreach to modify existing reservations

• 9% commission on upsell revenue 
  
  Customer testimonials mention that users get more extra bookings with the gap night feature.

  
  

Pricing Comparison Between Enso Connect and Besty AI

Enso Connect Pricing

Enso offers tiered pricing based on the number of properties and key features enabled:

• Price calculator is available (estimated, varies by features)

• Discounts for more listings and subscription, quarterly and yearly commitment apply 

• Includes: Boarding Pass guest app, automations, CRM for target marketing, upsells, EnsoAI (limited-time offer). 

• Upsell commission: 5% on revenue generated

• Damage waiver: 7% guest-paid fee

• Enterprise pricing available for larger portfolios and boutique hotels

• ROI Guarantee: Generate at least your subscription cost or continue using free

Besty AI Pricing

Besty uses a tiered per-listing model for vacation rentals:

• Pricing information is not disclosed in public sources

• Free demo: 14 days, no credit card required

• Upsell commission: 9% on revenue generated 

•  AI features included in a single plan

User Experience and Setup

Enso Connect's Onboarding and Support 

Onboarding

Enso Connect customers report a thorough onboarding process led by a dedicated team, offering hands-on expertise throughout the setup. This includes configuring automations, customizing the guest app and Boarding Pass, building digital guidebooks, setting up check-in flows and upsells, and integrating smart home technologies for automated access codes. In some cases, a white-glove onboarding service is available. A key advantage of Enso Connect’s AI system is that it learns organically through everyday use of the unified messaging inbox—eliminating the need for separate AI training sessions.

Support

Enso Connect's support team is known for quick and helpful responses to customers' queries. 

Besty's Onboarding and Support 

Onboarding

Quick setup process, described as a "5-minute" deployment time. 

Support

Feedback from Besty AI users: "Tech Support: No one seems to be working there on the weekends. There is a person on the help chat, but for technical issues there is little to no help during nights or weekends."

Integration Ecosystem Within Property Management Systems

Enso offers broader ecosystem connectivity for hospitality business operations, while Besty is catching up, adding more integrations. 

Ideal Use Cases for Different Vacation Rental Operations

Choose Enso Connect If You:

• Want a reliable AI that can set your guest messaging on autopilot 

• Need a branded guest app to deliver 5-star guest experience

• Manage boutique hotels or multiple property types (especially requiring different PMS)

• Value extensive customization and conditional automation for operational efficiency

• Want to consolidate multiple tools into one tech stack to reduce tech bloat

• Need robust smart lock integration with automated access codes

• Prioritize revenue optimization with upsells, local experiences, and damage waivers 

• Seek quick and helpful onboarding and support

• Make data-driven decisions using internal analytics dashboard

• Want to reduce guest interactions through proactive tools, like guest apps or digital guidebooks

• Need target marketing capabilities using guest data and CRM features

Choose Besty AI If You:

• Need an AI chatbot to automate your messaging 

• Want a quick setup with minimal configuration

• Focus heavily on capturing gap night revenue from Airbnb, VRBO, and Booking channels

• Manage vacation rentals where a branded guest app isn't essential

• Want to try AI features before expanding to other property management software

• Need faster response times without extensive human interaction

• Already have other tools in your tech stack for the guest app and smart locks integration

Feature Comparison Table: Important Features Analysis

The Verdict: Deeper AI, Better Support and Airbnb Integration

If you're a hospitality professional evaluating AI-powered guest messaging and upsell automation tools, here's how these platforms compare:

Enso Connect is best suited for short-term rental operators with 10+ properties seeking a comprehensive guest experience platform. It delivers advanced AI capabilities, a branded guest app with an intuitive upsell storefront, and dedicated onboarding support. Choose Enso if you prioritize operational efficiency, scalable, high-quality guest experiences, and revenue optimization through a unified platform.

Besty AI offers a streamlined AI messaging assistant focused on automating guest communication and capturing upsell opportunities like late checkouts and gap nights. It provides fast deployment with minimal configuration requirements, making it suitable for operators who need quick implementation with a focused feature set.

Important consideration for Airbnb hosts: Enso Connect is an official Airbnb partner with verified integration, while Besty AI operates without official Airbnb partnership status. This may affect integration reliability, feature access, and platform compliance for properties heavily reliant on Airbnb bookings.

Frequently Asked Questions from Hospitality Professionals

Q: Can I try both guest experience platforms before committing?
A: Yes. Enso Connect offers free demo sessions with their team and the ROI guarantee program; Besty AI provides a 14-day free trial with no credit card required, available today for immediate testing with your vacation rentals.

Q: Which platform has better AI features accuracy?
A: Both platforms promise high accuracy; however, 60% of Besty's reviews mention inaccurate answers in case questions go beyond standard FAQs. Enso emphasizes transparency in AI tools' reasoning and smart handoff to humans when confidence is low, while Besty relies on smart handoff and the abilities of AI to learn from conversations.

Q: Do these platforms work with my property management systems?
A: Both offer direct integration with major PMSs, including Hostaway, Guesty, Hostfully's and Lodgify PMS. Check each vendor's integration list for your specific property management software to ensure seamless PMS workflows and data synchronization.

Q: What about customer support and onboarding team assistance?
A: Enso provides dedicated onboarding and support team with hands-on expertise for setup and troubleshooting. Besty offers email and meeting support, though some user reviews note limited availability, with reports of slower response times for technical issues.

Q: Which platform is better for international vacation rentals?
A: Both support multiple languages for guest communication., auto-translating messages to 200+ languages. Enso Connect's guest app is customizable by region for different languages. WhatsApp integration reduces costs of international conversations.

Q: How quickly can I achieve operational efficiency with these platforms?
A: Besty is available with a quick setup for immediate faster response times, though AI requires a training period. Enso's onboarding team provides dedicated hands-on expertise over several weeks to configure all important features properly, but delivers more comprehensive operational efficiency across operational workflows, smart locks, upsells and AI training once fully deployed.

Q: Do these solutions help reduce business headaches, guest messages and phone calls?
A: Yes. Both platforms significantly reduce guest queries through automated responses and AI features. Enso's comprehensive digital guidebooks and guest app minimizes guest interactions by providing them with self-service information for a 5-star guest experience. Both AI-driven tools focus on faster response times to prevent guest questions from becoming phone calls or complaints.