# GuestWisely Software Reviews, Demo & Pricing - 2026 > Review of GuestWisely Software: system overview, features, price and cost information. Get free demos and compare to similar programs. Source: https://www.softwareadvice.com/property/365villas-profile --- [Home](https://www.softwareadvice.com/) / [Vacation Rental Software](https://www.softwareadvice.com/vacation-rental/) / GuestWisely Software Advice offers objective insights based on verified user reviews and independent product and market research. When our advisors match you to a software provider, we may earn a referral fee. Overview [Reviews](https://www.softwareadvice.com/property/365villas-profile/reviews/)[Alternatives](https://www.softwareadvice.com/property/365villas-profile/alternatives/) # GuestWisely 2026: Benefits, Features & Pricing Wondering if GuestWisely is right for your organization? Our Vacation Rental Software selection experts can help you in 15 minutes or less. On this page - Overview - User Interface - Popular Alternatives - Pricing and Plans - Features - Integrations - User Reviews - Popular Comparisons ## Overview GuestWisely 4.7 [(188)](https://www.softwareadvice.com/property/365villas-profile/reviews/) Pricing Pricing available upon request ### About GuestWisely GuestWisely is a comprehensive, cloud-based vacation rental management software designed for professional property managers with 10 or more properties. Trusted in over 60 countries, it combines powerful functionality with ease of use, giving managers full control over their operations from a single platform. With GuestWisely, you can manage every aspect of your vacation rental business — from reservations and guest communication to accounting, reporting, and direct bookings — without relying on third-party tools. The platform brings together a fully integrated Property Management System (PMS), real-time Channel Manager, Automated Guest Messaging, Owner Portals, Accounting Suite, and Direct Booking Website Tools, making it ideal for businesses looking to scale without increasing overhead. Key Features: - Centralized Reservation Management: Sync bookings, calendars, and availability across all listings and platforms in real time. - Advanced Channel Manager: Seamlessly connect to Airbnb, Vrbo, Booking.com, Expedia, and more with two-way integrations. - Automated Guest Communication: Set up smart, multilingual messages triggered at each stage of the guest journey. - Built-in Accou... nting Tools: Automate invoices, reconcile payments, manage owner payouts, and generate custom financial reports. - Direct Booking Website Builder: Create a fully integrated, SEO-optimized website with secure payment processing and dynamic content. - Unified Inbox: Manage all guest and platform communications in one place, with smart filters and templates. - Owner Access & Reporting: Provide owners with real-time access to performance metrics, booking activity, and statements. - Multi-Currency & Multi-Language Support: Operate across regions with confidence, including compliance with international tax structures. - Custom Development Options: Tailor the system to your business with dedicated development services when needed. - Team & User Management: Assign roles and access permissions across staff, vendors, and accounting teams. Why Property Managers Choose GuestWisely: - Purpose-built for professionals with 10+ properties - Recognized by Gartner as a FrontRunner for vacation rental software - Preferred Partner of Airbnb and Vrbo, ensuring certified, reliable OTA integrations - Trusted by clients in 60+ countries - Dedicated Account Manager assigned to every client - Transparent pricing and scalable plans with no hidden fees - Continuous platform improvements and feature releases - Secure cloud-based infrastructure with GDPR compliance Whether you're a growing agency or an established operator managing hundreds of properties, GuestWisely helps you save time, streamline operations, and grow smarter. From automated workflows to deep reporting and direct bookings, it’s the all-in-one platform built for serious short-term rental professionals. Book a demo to see how GuestWisely can support your business and help you scale with confidence. Wondering if GuestWisely is right for your organization? Our Vacation Rental Software selection experts can help you in 15 minutes or less. ## GuestWisely User Interface ## Popular GuestWisely Alternatives Main Product GuestWisely 4.7 [(188)](https://www.softwareadvice.com/property/365villas-profile/reviews/) Ratings Breakdown - 4.60Ease of use - 4.63Value for money - 4.79Customer support - 4.59Functionality Pricing Available upon request Get Price Alternative Product [Hostaway](https://www.softwareadvice.com/hotel-management/hostaway-profile/) 4.8 [(1575)](https://www.softwareadvice.com/hotel-management/hostaway-profile/reviews/) Ratings Breakdown - 4.59Ease of use - 4.56Value for money - 4.72Customer support - 4.65Functionality Pricing Available upon request Get Price Alternative Product [Lodgify](https://www.softwareadvice.com/hotel-management/lodgify-profile/) 4.5 [(1310)](https://www.softwareadvice.com/hotel-management/lodgify-profile/reviews/) Ratings Breakdown - 4.39Ease of use - 4.34Value for money - 4.56Customer support - 4.37Functionality Pricing Starting at $14.00 per month Get Price Alternative Product [Guesty Lite](https://www.softwareadvice.com/hotel-management/guesty-for-hosts-profile/) 4.7 [(547)](https://www.softwareadvice.com/hotel-management/guesty-for-hosts-profile/reviews/) Ratings Breakdown - 4.56Ease of use - 4.54Value for money - 4.42Customer support - 4.60Functionality Pricing Starting at $16.00 per month Get Price Alternative Product [Guesty](https://www.softwareadvice.com/hotel-management/guesty-profile/) 4.4 [(478)](https://www.softwareadvice.com/hotel-management/guesty-profile/reviews/) Ratings Breakdown - 4.41Ease of use - 4.16Value for money - 4.25Customer support - 4.38Functionality Pricing Starting at $23.00 per month Get Price Alternative Product [Breezeway](https://www.softwareadvice.com/vacation-rental/breezeway-profile/) 4.6 [(195)](https://www.softwareadvice.com/vacation-rental/breezeway-profile/reviews/) Ratings Breakdown - 4.63Ease of use - 4.53Value for money - 4.60Customer support - 4.47Functionality Pricing Starting at $6.00 per month Get Price ## GuestWisely Pricing and Plans Starting price: Connect with an advisor for pricing Free Trial Free Version Basic Pricing available upon request No plan information available Confused about pricing? We've got you covered. Get a personalized pricing breakdown tailored to your specific needs—no guesswork, no generic estimates. ## GuestWisely Features - Popular features found in Vacation Rental Availability Management Channel Management Contact Management Guest Experience Management Housekeeping Management Marketing Automation Online Booking Owner Statements Payment Processing Property Management Reservations Management Work Order Management - More features of GuestWisely Accounting Activity Dashboard Activity Tracking Alerts/Notifications API Billing & Invoicing Calendar Management Communication Management Content Management Credit Card Processing Credit Check Customizable Reports Customizable Templates Dashboard Data Import/Export Data Synchronization Digital Signature Discount Management Document Management Drag & Drop Dynamic Pricing Electronic Payments Electronic Signature Email Management Email Templates Expense Tracking File Sharing Financial Management Financial Reporting For Hospitality Industry For Vacation Rentals Guest Check-in/Check-out Guest Communications Guest Tracking Inbox Management Inspection Management Inventory Management Invoice Management Late Fee Calculation Lead Management Lease Tracking Listing Management Maintenance Management Maintenance Scheduling Marketing Management Mobile Access Multi-Channel Distribution Multi-Channel Management Multi-Currency Multi-Location Multi-Property Occupancy Management Online Payments Overdue Payments Owner Portal Performance Metrics Property Database Rate Management Ratings/Reviews Real-Time Notifications Real-Time Updates Recurring/Subscription Billing Reminders Rental Management Rent Tracking Reporting & Statistics Revenue Management Search/Filter Short/Long Term Rental Task Management Tax Management Template Management Tenant Portal Tenant Tracking Third-Party Integrations Transaction History Transaction Management Vacancy Management Vendor Management Website Management Workflow Management ## GuestWisely Integrations WhatsApp Integration rated undefined from -1 review Mailchimp Integration rated undefined from -1 review PayPal Integration rated undefined from -1 review authorize.net Integration rated undefined from -1 review Stripe Integration rated undefined from -1 review Operto Teams Integration rated undefined from -1 review See all 33 integrations ## GuestWisely User Reviews Overall Rating 4.7 Ratings Breakdown 5 78% 4 19% 3 2% 2 1% 1 1% Secondary Ratings Ease of Use 4.6 Value for money 4.6 Customer support 4.8 Functionality 4.6 JJ Jacqueline J. Verified reviewer Real Estate 2-10 employees Used daily for more than 2 years Review source Reviewed May 2019 Great Service, Software and Ease of Use 5 We have grown substantially since moving from an excel sheet and emails to the 365 Software. In 3 years we went from 15 properties to 35. It is very nice to be confident in the software as you grow, its a nice peace of mind to have, and one more thing to not have to worry about as we increase our revenues and number of apartments. Ratings Breakdown 5 Ease of use Previously 4 5 Value for money 5 Customer support 5 Functionality Pros: I have used 365 Villas over the past 3 years, and could not be more happy with my choice to use them as our core reservation management software. It is easy to use, syncs with many platforms, allows us to have a booking engine on our website, so we can get direct bookings, and the customer service is FANTASTIC! They have adjusted things in the past as they were growing and so were we, to accommodate our needs and they always work with a high level of honestly and respect of their clients. Cons: The air bnb messaging does not sync yet with the software, but reservations and the two way syncing works great! I believe the messaging feature is coming soon, as 365 is constantly improving the software and options offered. Read More NM Nancy M. Verified reviewer Leisure, Travel & Tourism Self-Employed Used daily for less than 2 years Review source Reviewed December 2024 365 Villas Customer Service is Excellent 5 I have had 365villas for approximately 1 year. I waited this long to do the review as I was waiting until I was able to utilize all the features. It took me a long while to set up the online platform - Caribbean banking system. Once I was ready to go 365villas was there to help do the final steps. I am pleased overall. They are always looking at ways to improve and make the product even better. I would highly recommend 365villas. Ratings Breakdown 5 Ease of use 5 Value for money 5 Customer support 5 Functionality Pros: Initially, it was an affordable option for my small property management company. It was a leap of faith for any of the systems out there, as it does take some initial work to get it up and running. I did have a few hurdles and feel the support team has been there every step of the way. You can reach out to support at anytime and the turnaround time is very efficient. It was fairly easy to upload the properties and super easy to make edits and updates once set up. Cons: If I had to find one thing, I am not a huge fan of the email layout in the system. I am getting used to it but does not feel intuitive for me. Reasons for choosing GuestWisely Price point was probably the deciding factor as I am a small business. Read More DL David L. Real Estate 2-10 employees Used unspecified for more than 2 years Review source Reviewed February 2019 This is the best out there. 5 Since we have been using 365 our business is growing and our customers and clients are very happy. I researched a lot of similar options and by far 365 is the best platform, easy to use and covers all the details of our vacation rental business. Ratings Breakdown 5 Ease of use 5 Value for money 5 Customer support 5 Functionality Pros: They have an all in one solution from accounting to reservation management. Cons: Nothing everything is great. The platform is easy to use. Read More JF Jamie F. Verified reviewer Hospitality 11-50 employees Used daily for more than 2 years Review source Reviewed December 2024 Fabulous Software and Great Customer Support! 5 Great experience! We have been with 365 Villas for over 5 years and it gets better every month! In particular, \[sensitive content hidden\] has been a lifesaver over the years and so patient and helpful in explaining details and helping with training and support needed through product enhancements and transitions. Ratings Breakdown 5 Ease of use 5 Value for money 5 Customer support 5 Functionality Pros: The customer support and the constant enhancements 365 Villas is doing to better the product and keep up with industry trends. Cons: Some of the synchronization issues with Airbnb Reasons for choosing GuestWisely The price for a small startup company was better as you pay as you grow the number of properties you manage with 365 Villas Read More TS Toine S. Verified reviewer Real Estate 2-10 employees Used daily for less than 6 months Review source Reviewed November 2024 Excellent and comprehensive program for all short term rental managers! 5 It is a complete product, the onboarding was very easy and the product is complete. Our team just started working with it but they all love it. \[sensitive content hidden\] was very helpful with the onboarding process Ratings Breakdown 5 Ease of use 5 Value for money 5 Customer support 5 Functionality Pros: Response of the 365 Villa's team Great onboarding with \[sensitive content hidden\] user friendly interface with the bolt on options you can customize the package to what you need We gave a suggestion for the history of owner bookings and they made it happen quickly! Cons: no mobile app onboarding process takes long (but serves as a training and setting up the system) Reasons for choosing GuestWisely user friendly and reviews that we read online. Reasons for switching to GuestWisely more comprehensive solution was required for our growing business Read More WP Wallace P. Verified reviewer Hospitality Self-Employed Used daily for less than 2 years Review source Reviewed November 2024 Efficiency with 365Villas 5 The support team and account manager makes the use of tool very effective. Ratings Breakdown 5 Ease of use 3 Value for money 5 Customer support 5 Functionality Pros: The single point of communicating and finances makes using multiple channels easy to manage. Cons: The on-boarding process and time it takes to be productive takes a bit, but I don’t know if other competitors tools would be more quicker. Reasons for choosing GuestWisely Great review score by other users help me decide to go with 365Villas. Read More RO Rachel O. Verified reviewer Hospitality 2-10 employees Used daily for more than 2 years Review source Reviewed July 2025 Very happy with our 365 Villas Software 5 I'm very happy with the software. It's changed how we operate our bunisess and has given us the tools we needed to grow. Ratings Breakdown 5 Ease of use 5 Value for money 5 Customer support 5 Functionality Pros: The software is robust and allows you to pick and choose which modules you would like to have, based on your business needs. I love the website integration and booking manager. It has really helped to organize our bookings so that we don't miss anything and it can be shared across our entire team. Cons: As with any software, it is a lot to learn. I recently added the channel manager to my account, and that has been another steep learning curve. Maybe it would help to have continual group training sessions on different topics. Vendor Response Hello Rachel, Thank you for sharing your experience! We're glad to hear that 365Villas has helped simplify your operations and support your business growth. Our modular approach is designed exactly for what you mentionned: giving you the flexibility to tailor the platform to your specific needs. We appreciate your feedback on the learning curve with new features like the Channel Manager. Ongoing training is something we’re actively working to expand, and your suggestion for group sessions is a great one. It's exciting to hear how the platform is making a real impact for you and your team, and we’re here to support you as you continue to grow. Thank you so much! Replied July 2025 Read More KW Katherine W. Verified reviewer Hospitality 2-10 employees Used daily for less than 2 years Review source Reviewed May 2025 Great platform. Loving it. Highly recommend. 5 I am extremely satisfied with 365Villas. Since using them with my website, my bookings have exceeded my other paid platform bookings. 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. Ratings Breakdown 4 Ease of use 4 Value for money 5 Customer support 5 Functionality Pros: 365Villas is easy to use with so many tools tools to help me succeed. Cons: Finding the tools I need is often difficult. They are strangely arranged. Vendor Response Dear Katherine, Thank you for taking the time to share your experience! We're so happy to hear that 365Villas has helped boost your direct bookings and that you're finding value in the tools we provide. It’s especially rewarding to know that our proactive customer support has made a positive impression. We also appreciate your honesty regarding the tool layout. Your feedback is incredibly valuable, and we’re constantly working to improve the user experience. We’ll be sure to pass this along to our product team as we continue refining the platform. Thanks again for your kind words and for being part of the 365Villas community. We're excited to keep supporting your success! The 365Villas Team Replied June 2025 Read More VR Verified Reviewer Real Estate Self-Employed Used daily for less than 12 months Review source Reviewed July 2025 Great tool 4 I really enjoy using this platform and love how it is connected to Ari BnB, so it is easy for me to manage everything. Ratings Breakdown 4 Ease of use 4 Value for money 4 Customer support 4 Functionality Pros: It is easy to use to manage the property and there are a lot of options that make booking and managing easier. Cons: It is a little pricy when I first started because it is part of the investment, so it was just part of the budget. Read More IV Inês V. Verified reviewer Real Estate 2-10 employees Used daily for less than 6 months Review source Reviewed June 2025 Great platform and great team 5 As a property management company, we were looking for a channel manager to integrate different properties in different booking platforms. We found 365Villas and we are very happy. The team is very attentive, helpful and efficient. Answers are given as quickly as possible and they care about the customer. After purchasing the package, several free learning sessions are given and if any further questions arise, the team is available to arrange more sessions. I would especially like to thank Hind, Irina and Leonardo for all the patience and time they gave and are giving to help. Thank you. Ratings Breakdown 5 Ease of use 5 Value for money 5 Customer support 5 Functionality Pros: The platform is relatively simple to navigate and quite complete. It takes just a few sessions with the team to start understanding how this channel manager works Cons: I dont have anything bad to say about 365 villas. Everything went well and according to my expectations. Vendor Response Dear Inês, Thank you so much for your thoughtful and generous review! We're delighted to hear that 365Villas has met your expectations and made managing your properties across multiple platforms easier. It’s great to know that the platform’s simplicity and completeness have been a good fit for your property management company. A special thank you for recognizing Hind, Irina, and Leonardo — we're incredibly proud of our team, and it's wonderful to see their dedication reflected in your experience. Providing an attentive and efficient support is something we truly value, so we're thrilled to know it made a difference for you. If there's anything else we can do to support your success in the future, we're always here for you. Thanks again for being a valued part of the 365Villas community! The 365Villas Team Replied June 2025 Read More Showing 1 - 10 of 188 Reviews [See All Reviews](https://www.softwareadvice.com/property/365villas-profile/reviews/) ## GuestWisely Popular Comparisons [Hostaway vs GuestWisely](https://www.softwareadvice.com/property/365villas-profile/vs/hostaway/)[Lodgify vs GuestWisely](https://www.softwareadvice.com/property/365villas-profile/vs/lodgify/)[Guesty Lite vs GuestWisely](https://www.softwareadvice.com/property/365villas-profile/vs/guesty-for-hosts/)[Guesty vs GuestWisely](https://www.softwareadvice.com/property/365villas-profile/vs/guesty/) [Compare All Alternatives](https://www.softwareadvice.com/property/365villas-profile/alternatives/) ## Other Top Recommended Vacation Rental Software [Hostaway](https://www.softwareadvice.com/hotel-management/hostaway-profile/) **4.8** (1575) Recently recommended **8** times [Hostfully Guidebooks](https://www.softwareadvice.com/hotel-management/hostfully-profile/) **4.8** (123) Recently recommended **7** times [rezStream](https://www.softwareadvice.com/vacation-rental/rezstream-profile/) **4.7** (118) Recently recommended **6** times [Guesty](https://www.softwareadvice.com/hotel-management/guesty-profile/) **4.4** (478) Recently recommended **3** times Stuck Between Options? 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