GuestWisely 2026: Benefits, Features & Pricing
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- Overview
- Pricing and Plans
- Features
- Integrations
- User Reviews
Overview
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:
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Centralized Reservation Management: Sync bookings, calendars, and availability across all listings and platforms in real time.
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Advanced Channel Manager: Seamlessly connect to Airbnb, Vrbo, Booking.com, Expedia, and more with two-way integrations.
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Automated Guest Communication: Set up smart, multilingual messages triggered at each stage of the guest journey.
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Built-in Accou...
GuestWisely Screenshots

GuestWisely Pricing and Plans
Basic
Pricing available upon request
No plan information available

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GuestWisely Features
- Popular features found in Vacation RentalAvailability ManagementChannel ManagementContact ManagementGuest Experience ManagementHousekeeping ManagementMarketing AutomationOnline BookingOwner StatementsPayment ProcessingProperty ManagementReservations ManagementWork Order Management
- More features of GuestWiselyAccountingActivity DashboardActivity TrackingAlerts/NotificationsAPIBilling & InvoicingCalendar ManagementCommunication ManagementContent ManagementCredit Card ProcessingCredit CheckCustomizable ReportsCustomizable TemplatesDashboardData Import/ExportData SynchronizationDigital SignatureDiscount ManagementDocument ManagementDrag & DropDynamic PricingElectronic PaymentsElectronic SignatureEmail ManagementEmail TemplatesExpense TrackingFile SharingFinancial ManagementFinancial ReportingFor Hospitality IndustryFor Vacation RentalsGuest Check-in/Check-outGuest CommunicationsGuest TrackingInbox ManagementInspection ManagementInventory ManagementInvoice ManagementLate Fee CalculationLead ManagementLease TrackingListing ManagementMaintenance ManagementMaintenance SchedulingMarketing ManagementMobile AccessMulti-Channel DistributionMulti-Channel ManagementMulti-CurrencyMulti-LocationMulti-PropertyOccupancy ManagementOnline PaymentsOverdue PaymentsOwner PortalPerformance MetricsProperty DatabaseRate ManagementRatings/ReviewsReal-Time NotificationsReal-Time UpdatesRecurring/Subscription BillingRemindersRental ManagementRent TrackingReporting & StatisticsRevenue ManagementSearch/FilterShort/Long Term RentalTask ManagementTax ManagementTemplate ManagementTenant PortalTenant TrackingThird-Party IntegrationsTransaction HistoryTransaction ManagementVacancy ManagementVendor ManagementWebsite ManagementWorkflow Management
GuestWisely Integrations
See all 33 integrations
GuestWisely User Reviews
Overall Rating
4.7
Ratings Breakdown
5
77%
4
20%
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

Taylor J. W.
Verified reviewer
Hospitality
2-10 employees
Used daily for less than 6 months
Review sourceReviewed January 2021
Easy & effective to use PLUS an outstanding support team to help you along the way!
5
Our company had recently switched from a different PMS system to 365Villas and we couldnt be happier. The product and its interface is very easy to understand and extremely easy to use. Not to mention the options are limitless! Our experience with the team at 365Villas has been nothing short of amazing! The transition, onboarding and the ongoing support has been greatly apprecited and everything has been seamless. Our account manager and all the team members that have helped us thus far have all been extremely patient in answering all of our questions and making sure that we understand the full capacity of the system and its add-ons. They have even gone a step further to show us all of the ins and outs of the specific channels that we are connecting to, to make sure that we are using them to their full potential - This is something that we didnt have in the past and we greatly appreciate! I would 100% recommend 365Villas! Thank you 365Villas, you have a client for life!
Ratings Breakdown
Vendor Response
Dear Taylor, We are very grateful for this thoughtful review. Thanks for taking the time. It's a pleasure to have you and your team with us. The 365Villas Team
Replied January 2022
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David H.
Verified reviewer
Real Estate
2-10 employees
Used daily for less than 6 months
Review sourceReviewed July 2025
365Villa’s Support Team: Above and Beyond
5
My interaction was almost exclusively with [sensitive content hidden]. From our first interaction, your patience, professionalism and genuine commitment have stood out. You consistently went above and beyond, spending way more time with me than I ever expected, answering every question and anticipating next steps before I even knew I’d need help. Whenever I reached out, I received a prompt, proactive response. Whenever I encountered an issue, either you or another support team member followed up immediately until everything I had raised was either answered or resolved. Onboarding this new system has been daunting, especially with so many moving parts and considerations and my lack of experience in the business. I’d be lying if I said I wasn’t totally overwhelmed and a bit nervous to move to production, especially as it relates to the money collection, movement and deposit taking! That said, with the responsive support network that you have, I feel confident that I’ll be able to get the assistance if and when needed. Your attentiveness and expertise made the process less stressful and a far more of a positive experience than I was expecting. I’m sincerely grateful for the dedication and time you spent with me I and look forward to continuing and growing our partnership. I’ve got a commitment for another property that should start in a few weeks and I’m confident that this is just the beginning.
Ratings Breakdown
Reasons for choosing GuestWisely
Integration with payment processor, cost model, breadth of offering.
Vendor Response
Thank you for your thoughtful review and for choosing 365Villas as your partner. We’re delighted to hear that the onboarding experience and support exceeded your expectations. Our team takes pride in making sure every client feels guided and supported, especially during the early stages. We understand the challenges of launching as a startup PM, and your feedback on the pricing model is appreciated and will be taken into consideration. It’s great to know our platform’s breadth and integration capabilities stood out to you. We’re excited about your growth and are here to support you if you need. Congratulations on your next property by the way! We’re sure this is just the beginning of a successful partnership!
Replied July 2025
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Jacqueline J.
Verified reviewer
Real Estate
2-10 employees
Used daily for more than 2 years
Review sourceReviewed 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
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Ramon F.
Verified reviewer
Real Estate
11-50 employees
Used daily for less than 12 months
Review sourceReviewed October 2025
Promising system that falls short in key areas
2
We used the system for around 10 months and invested a significant amount in the setup. GuestWisely offers some great features, but there is still a lot of manual work required. Channel connectivity was unreliable, and although we requested multi-unit Airbnb support from the start, it was finally confirmed as not available. We had to create workarounds that were far from ideal and led to lost bookings. The lack of a mobile app also made daily operations more difficult, as our team had to log in through a web browser to check updates. Ultimately, we decided to move away from GuestWisely mainly due to poor customer service, connectivity issues, and the absence of proper multi-unit functionality.
Ratings Breakdown
Reasons for choosing GuestWisely
Looked clean and professional with a great direct website interface.
Reasons for switching to GuestWisely
The system was setup for single property locations und not a multi property setup. More usefull for a hotel or a proeprty that has many units in the same place. Its a fantastic system for daily operation and a very strong channel manager. Finally we move form GuestWisely to Guesty and are super happy.
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Rich B.
Verified reviewer
Hospitality
2-10 employees
Used daily for less than 6 months
Review sourceReviewed October 2025
A Fantastic Property Management Software
5
It has been remarkable. Definitely the best thing to happen to my business and the support across all aspects from setup, to connectivity to website has been first class
Ratings Breakdown
Reasons for choosing GuestWisely
The biggest upside is that GuestWisely intgrates into a South African payment provider - Paygate
Reasons for switching to GuestWisely
Significantly more functionality at significantly lower cost
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Nancy M.
Verified reviewer
Leisure, Travel & Tourism
Self-Employed
Used daily for less than 2 years
Review sourceReviewed 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
Reasons for choosing GuestWisely
Price point was probably the deciding factor as I am a small business.
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Jamie F.
Verified reviewer
Hospitality
11-50 employees
Used daily for more than 2 years
Review sourceReviewed 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
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
Elizabeth T.
Verified reviewer
Hospitality
2-10 employees
Used daily for less than 2 years
Review sourceReviewed August 2024
Best Property Management system around
5
Our overall on boarding experience was excellent with the personnel conducting the training being very well qualified and patient with our requests . If we had queries, they would answer them immediately or can’t find any information that we needed and customise the execution of our needs within the system. There were many times where our individual needs had not been included in the original package and 365 worked very hard to accommodate these situations
Ratings Breakdown
Reasons for switching to GuestWisely
More features in 365. Direct integration with Airbnb, calendar sync available, great customer service and personalised help with customisation of systems needed for our particular country
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Marc L.
Verified reviewer
Consumer Services
2-10 employees
Used daily for less than 6 months
Review sourceReviewed December 2025
A wonderful experience
5
I had an excellent experience! In less than a month, I accomplished a lot and I am almost ready to launch the business. Thank you [sensitive content hidden] !
Ratings Breakdown
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Real Estate
Self-Employed
Used daily for less than 12 months
Review sourceReviewed 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
Read More
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