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GuestWisely Logo

Powering Growth for Vacation Rental Professionals

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GuestWisely - 2026 Pricing, Features, Reviews & Alternatives

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All user reviews are verified by in-house moderators and provider data by our software research team.  Learn more

Last updated: January 2026

GuestWisely overview

What is GuestWisely?

GuestWisely is a leading, cloud-based vacation rental software platform built for professional property managers managing 10 or more properties. Trusted in over 60 countries, GuestWisely provides an all-in-one, fully integrated system designed to streamline complex operations, automate repetitive tasks, and support sustainable business growth in the competitive short-term rental market.

Built with scalability and customization in mind, GuestWisely combines powerful tools into a single platform — eliminating the need for third-party plugins or workarounds. Whether you manage 10 listings or 500, you’ll have access to the same enterprise-grade features, including:

🌐 Advanced Property Management System (PMS)

Manage bookings, calendars, availability, and guest data from a centralized dashboard. Automate repetitive workflows like confirmations, follow-ups, and scheduling with minimal manual input. Flexible rules let you configure rates, fees, and policies at a granular level.

🔗 Channel Manager

Connect to Airbnb, Vrbo, Booking.com, Expedia, Google Vacation Rentals, and more. Real-time two-way sync helps avoid double bookings and reduces time spent updating availability manually. As a Preferred Partner of both Airbnb and Vrbo, GuestWisely ensures stable, certified integrations.

📩 Unified Messaging & Guest Communication

Use one central inbox to manage all communications across platforms. Set up automated, multilingual templates for every stage of the guest journey — from inquiry to review requests. Personalization fields, conditional logic, and smart triggers offer precision and consistency.

📈 Integrated Accounting & Owner Reporting

Track payments, generate owner statements, automate invoices, and reconcile transactions in multiple currencies. Built-in accounting tools are designed to reduce complexity without relying on external tools like Xero or QuickBooks (though integrations are available if needed).

📊 Reports & Analytics

Access real-time dashboards and custom performance reports to stay on top of occupancy, revenue, cancellations, and owner performance. Export data easily or set up scheduled reports for stakeholders.

🧰 Customization & Developer Support

For businesses with unique workflows, GuestWisely offers tailored configurations and custom development services. Whether it’s syncing with a niche third-party system, custom reporting modules, or advanced owner access controls, the platform can be adapted to fit.

📱 Direct Booking Website & Guest Experience Tools

Launch a modern, mobile-optimized direct booking website with SEO features, payment gateways, upsell integrations, and multi-language content. You can also enable self-check-in, digital guidebooks, and dynamic pricing powered by integrations with Beyond or PriceLabs.

👥 User Management & Permissions

Manage access levels for internal staff, cleaners, accountants, and partners with detailed permission settings. This ensures operational clarity and data security across growing teams and multiple roles.

Whether you’re a fast-scaling agency or an established vacation rental operator, GuestWisely equips you with the tools and support you need to scale smarter — not harder.

Book a free demo or get in touch to see how GuestWisely can streamline your operations and drive real growth.

Key benefits of using GuestWisely

Key Benefits of Using GuestWisely:

All-in-One Platform: PMS, channel manager, accounting, website builder, and guest communication in one unified system.

Built for Scale: Designed specifically for managers with 10+ properties — supports up to hundreds.

Automated Workflows: Save time with automated messaging, booking processes, invoicing, and reporting.

Real-Time Channel Sync: Avoid double bookings with certified, two-way integrations with Airbnb, Vrbo, and more.

Integrated Accounting: Full financial tools with multi-currency, tax rules, owner statements, and invoice automation.

Custom Development Available: Flexible enough to adapt to your unique business processes and integrations.

Direct Booking Power: Launch SEO-optimized websites with a built-in booking engine and payment gateway.

Global Ready: Multi-language, multi-currency, and VAT-compliant for international operations.

Dedicated Account Manager: Personalized onboarding and ongoing support from a real person who knows your business.

Preferred Partner Status: Trusted by major OTAs like Airbnb and Vrbo, and recognized as a Gartner FrontRunner.

Starting price

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Pros & Cons

Responsiveness

Navigation

Coordination

Stability

Analytics

GuestWisely’s user interface

Ease of use rating:

GuestWisely pros, cons and reviews insights

To determine these pros and cons insights, we analyzed responses from 

Overall rating

Reviews sentiment

 
 
 
1-2(3)
3-4(40)
5(142)

What do users say about GuestWisely?

Users say 365Villas offers responsive customer support, frequent updates, and a knowledgeable team that helps resolve issues quickly. They report the platform is effective for managing bookings, synchronizing calendars, and automating guest communications, which saves time and streamlines vacation rental operations. They appreciate the integrated accounting and reporting features, as well as the flexibility to handle multiple properties and owners.

Reviewers indicate the software is generally user-friendly after initial training, though some find the learning curve steep and setup overwhelming at first. They mention occasional bugs, limited real-time support, and desire more customization, but feel ongoing improvements address many concerns.

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Who uses GuestWisely?

Based on 185 verified user reviews.

Company size

Small Businesses

Enterprises

Midsize Businesses

Top industries

Hospitality
Real Estate
Leisure, Travel & Tourism
Consumer Services
Others

Use cases

Vacation Rental
Property Management
Online Property Management
Channel Management
Real Estate Property Management

GuestWisely's key features

Most critical features, based on insights from GuestWisely users:

Reservations management
For vacation rentals
Guest communications
Payment processing
Calendar management
Accounting

All GuestWisely features

Features rating:

Invoice management
Online booking
Data synchronization
Customizable templates
Vacancy management
Contact management
Communication management
Multi-Channel management
Activity dashboard
Credit card processing
Transaction history
Property database
Rent tracking
Overdue payments
Billing & invoicing
Owner statements
Online payments
Channel management
Third-Party integrations
Guest experience management
Housekeeping management
Lead management
Template management
Data import/export
Discount management
Marketing automation
Work order management
Owner portal
Performance metrics
File sharing
Property management
Rate management
Multi-Property
Ratings/Reviews
Occupancy management
Workflow management
Website management
Vendor management
Transaction management
Tenant tracking
Tenant portal
Tax management
Task management
Short/Long term rental
Search/Filter
Revenue management
Reporting & statistics
Rental management
Reminders
Recurring/Subscription billing
Real-Time updates
Real-Time notifications
Expense tracking
Email templates
Email management
Electronic signature
Electronic payments
Dynamic pricing
Drag & drop
Document management
Digital signature
Dashboard
Customizable reports
Credit check
Content management
Availability management
API
Alerts/Notifications
Activity tracking
Multi-Location
Multi-Currency
Multi-Channel distribution
Mobile access
Marketing management
Maintenance scheduling
Maintenance management
Listing management
Lease tracking
Late fee calculation
Inventory management
Inspection management
Inbox management
Guest tracking
Guest check-in/check-out
For hospitality industry
Financial reporting
Financial management

GuestWisely awards

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GuestWisely pricing

Value for money rating:

Starting from

Empty state illustration for "No pricing info"

No pricing info

Pricing details
Subscription
Free trial
Free plan
Pricing range

User opinions about GuestWisely price and value

Value for money rating:

To see what individual users think of GuestWisely's price and value, check out the review snippets below.

“I love that the owners can have access to 365 villas, its very important with the trust building.”
NK

Nikoletta K.

CEO

“The booking and guest communication features are also superb, very professionally written system templates, easy to customize and access. Overall great experience.”
MC

Marian C.

Owner

GuestWisely integrations (37)

Integrations rated by users

We looked at 185 user reviews to identify which products are mentioned as GuestWisely integrations and how users feel about them.

WordPress logo
WordPress

Integration rating: 5.0 (1)

Our website is built on Wordpress, and our vacation rentals are all automatically integrated and presented on the website, with availability calendars, pricing and booking functionality.

RO

Rachel O.

Owner and Administrator

Vrbo logo
Vrbo

Integration rating: 4.0 (1)

For now it's processes about a third of my bookings but sometimes experience a syncing issue

KW

Katherine W.

Owner

Integration rating: 4.3 (3)

PriceLabs logo
PriceLabs

Integration rating: 5.0 (3)

Stripe logo
Stripe

Integration rating: 5.0 (2)

PayPal logo
PayPal

Integration rating: 5.0 (1)

Breezeway logo
Breezeway

Integration rating: 5.0 (1)

PayGate logo
PayGate

Integration rating: 4.0 (1)

GuestWisely customer support

What do users say about GuestWisely customer support?

Customer support rating:

We analyzed 70 verified user reviews to identify positive and negative aspects of GuestWisely customer support.

Widely noted by reviewers, 365Villas offers prompt, responsive, and helpful customer support that addresses issues efficiently.

A fair number of users appreciate the personal approach and patience shown by support staff, including dedicated account managers.

A portion of users highlight that support is easily reachable, friendly, and proactive in checking in and assisting with needs.

Multiple users mention that support goes beyond troubleshooting, offering guidance, training, and even implementing requested features.

Support options

Knowledge base
Chat
24/7 (live rep)
Faqs/forum
Email/help desk
Phone support

Training options

Webinars
Live online
Videos
Documentation

To see what individual users say about GuestWisely's customer support, check out the review snippets below.

“It has all the main important tools to manage the business and when something is not working properly you have a wonderful customer service that are willing to constantly making improvements and quickly fix the little bugs. ”

Verified reviewer profile picture

Ana L.

Owner

“In an age where customer support and service are nonexistent, 365 has demonstrated a real interest in communicating with, responding to and in fact partnering with us to make our business better.”

MS

Mike S.

“I can't rave enough about their proactive customer support - they check in on you to make sure you don't have any issues or needs. And when you do need assistance, they are responsive and helpful.”

KW

Katherine W.

Owner

GuestWisely FAQs

Q. What type of pricing plans does GuestWisely offer?

GuestWisely has the following pricing plans:
Pricing model: Subscription


Q. Who are the typical users of GuestWisely?

GuestWisely has the following typical customers:
Freelancers, Large Enterprises, Mid Size Business, Small Business


Q. What languages does GuestWisely support?

GuestWisely supports the following languages:
English, French, Italian, Portuguese, Spanish


Q. Does GuestWisely support mobile devices?

GuestWisely supports the following devices:
Android, iPad, iPhone


Q. Does GuestWisely offer an API?

Yes, GuestWisely has an API available for use.


Q. What other apps does GuestWisely integrate with?

GuestWisely integrates with the following applications:
authorize.net, Adyen, PayPal, Zumper, Worldpay for Enterprise, Veem, Rentals United, WhatsApp, PayGate, PayU, Operto Teams, Shuttle, ECOMMPAY, Enso Connect, WordPress, Stripe, Paysafe, Opayo, GoCardless, Mollie, PriceLabs, Beyond, Vrbo, Global Payments Integrated, Divi, Google Pay, CardConnect, Judo, Amazon Pay, Mailchimp, Beyond, PayPal Enterprise Payments, Twilio, Chekin App, Breezeway, NMI Payments


Q. What level of support does GuestWisely offer?

GuestWisely offers the following support options:
Knowledge Base, Chat, 24/7 (Live rep), FAQs/Forum, Email/Help Desk, Phone Support

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