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GuestWisely

GuestWisely 2026: Benefits, Features & Pricing

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On this page
  • Overview
  • Pricing and Plans
  • Features
  • Integrations
  • User Reviews

Overview

GuestWisely
GuestWisely
4.7
(185)

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.

GuestWisely Screenshots

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GuestWisely Pricing and Plans

Free Trial
Free Version

Basic

Pricing available upon request

No plan information available

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    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
    WhatsApp
    Mailchimp
    Mailchimp
    PayPal
    PayPal
    authorize.net
    authorize.net
    Stripe
    Stripe
    Operto Teams
    Operto Teams

    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.'s profile

    Taylor J. W.

    Verified reviewer

    Hospitality

    2-10 employees

    Used daily for less than 6 months

    Review source

    Reviewed 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

    5
    Ease of use
    5
    Value for money
    5
    Customer support
    5
    Functionality
    icon
    Pros:
    365Villas has released a new, very user friendly interface for their PMS software which makes it easy to manage properties while on the go. Also, the responsiveness and dedication of the representative and support team remains unmatched!
    Cons:
    There are many add-on options to the software. This is not really a con as you use what you need. You can add on to you subscription as you need, but there is a fee.

    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

    Read More

    DH

    David H.

    Verified reviewer

    Real Estate

    2-10 employees

    Used daily for less than 6 months

    Review source

    Reviewed 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

    4
    Ease of use
    5
    Value for money
    5
    Customer support
    5
    Functionality
    icon
    Pros:
    The breadth of the offering is truly impressive and the support received and time spent towards training during the onboarding process exceeded all expectations.
    Cons:
    Difficult for me to speak to this given my near non-use of the platform so far. So far what I've been able to accomplish on the platform has met my expectations. To select one thing - I may call out the pricing plan and the need to lock in with 5 properties to start. As a startup PM, paying for properties you don't manage is difficult but if this cost is designed to offset training and onboarding, I get it.

    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

    Read More

    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
    icon
    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

    RF

    Ramon F.

    Verified reviewer

    Real Estate

    11-50 employees

    Used daily for less than 12 months

    Review source

    Reviewed 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

    3
    Ease of use
    2
    Value for money
    1
    Customer support
    2
    Functionality
    icon
    Pros:
    GuestWisely (former 365Villas) dashboard had a clean and simple layout that made it easy to manage all bookings efficiently. The direct website integration worked smoothly, and the automated message templates and workflow automation were very well designed. These features helped streamline communication and daily operations effectively.
    Cons:
    Customer service is very poor, especially during weekends when there is no support at all. We experienced many issues with channel connections. The onboarding process initially seemed professional, but in practice, there were frequent connectivity problems with the system. There’s also no mobile app to manage communications and operations on the go, and no real-time notifications. Another major limitation is the lack of proper multi-unit functionality with some channels like Airbnb, which forced us to recreate listings and lose valuable reviews. This had a significant impact on reservations and flexibility in assigning guests to different villa units.

    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.

    Read More

    RB

    Rich B.

    Verified reviewer

    Hospitality

    2-10 employees

    Used daily for less than 6 months

    Review source

    Reviewed 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

    5
    Ease of use
    4
    Value for money
    5
    Customer support
    5
    Functionality
    icon
    Pros:
    Guestwisely takes care of so many aspects of the business that it's hard to pinpoint any specific one. I can, however, say with confidence that introducing Guestwisely early on in my business has was the best business decision I have ever made
    Cons:
    When it was 365Villas, the back-end had a lot of latency. This has largely been sorted out since in migrated to Guestwisely.

    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

    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
    icon
    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

    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
    icon
    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

    ET

    Elizabeth T.

    Verified reviewer

    Hospitality

    2-10 employees

    Used daily for less than 2 years

    Review source

    Reviewed 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

    5
    Ease of use
    5
    Value for money
    5
    Customer support
    5
    Functionality
    icon
    Pros:
    I like its intuitive, ease of operation and very qualified staff.
    Cons:
    Some key features such as payment processing are not available in my country andI i feel that this should be remedied . I would like to see Booking.com be more Integrated with 365Villas.

    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

    Read More

    ML

    Marc L.

    Verified reviewer

    Consumer Services

    2-10 employees

    Used daily for less than 6 months

    Review source

    Reviewed 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

    3
    Ease of use
    4
    Value for money
    5
    Customer support
    5
    Functionality
    icon
    Pros:
    What I appreciated the most was, above all, the availability. I was always able to schedule an appointment within the same week. I really appreciated that the meetings lasted an hour, which is very generous compared to other platforms that sometimes offer only 15 to 30 minutes. I appreciated the professionalism of the people who supported me throughout this process and the time they devoted to me. Often, the meetings went a little beyond the scheduled time, and they always stayed with me a bit longer to answer my questions. I received exemplary support—better than I could have imagined. Guestwisely is a complex platform, but thanks to all the meetings I was able to attend, I managed to gain a good understanding of how it works. I also appreciated the respect I was shown. Since English is not my first language and I am new to managing rental chalets, I didn’t always understand things right away, but the people who supported me were always very respectful and patient with me. In short, thank you very much—this is a truly wonderful company!
    Cons:
    Almost nothing! Perhaps the complexity of the platform and the website at the beginning, or the fact that several option require payment. Aside from that, I have nothing to say.

    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
    icon
    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

    Showing 1 - 10 of 185 Reviews

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