GuestWisely 2026: Benefits, Features & Pricing

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Overview
Pricing and Plans
Features
Integrations
User Reviews

Overview

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...

GuestWisely Screenshots

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

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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

Mailchimp

PayPal

authorize.net

Stripe

Operto Teams

See all 33 integrations

GuestWisely User Reviews

Overall Rating

4.7

Ratings Breakdown

77%

20%

Secondary Ratings

Ease of Use

4.6

Value for money

4.6

Customer support

4.8

Functionality

4.6

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

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

Ease of use

Previously 4

Value for money

Customer support

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.

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!

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

Ease of use

Value for money

Customer support

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

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.

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

Ease of use

Value for money

Customer support

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.

Wallace P.

Verified reviewer

Hospitality

Self-Employed

Used daily for less than 2 years

Review source

Reviewed November 2024

Efficiency with 365Villas

The support team and account manager makes the use of tool very effective.

Ratings Breakdown

Ease of use

Value for money

Customer support

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.

Danilo B.

Verified reviewer

Hospitality

51-200 employees

Used daily for less than 6 months

Review source

Reviewed September 2024

A very good package

Great system especially because it connects to all major OTA and accounting systems.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

Easy to adapt from other system we used before. Very good customer Service and Training

Cons:

All good, just so many functions (which is good) but it take time to learn

Reasons for switching to GuestWisely

Guest charge per booking what become expensive, also no connection to our accounting system which makes it difficult for us since we needed to import it manual

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

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

Ease of use

Value for money

Customer support

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

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.

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

Ease of use

Value for money

Customer support

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

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

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

Ease of use

Value for money

Customer support

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

Andrina Darrell D.

Verified reviewer

Hospitality

2-10 employees

Used daily for less than 12 months

Review source

Reviewed August 2025

Great support, awesome pm tool with room of technical improvemt

Happy satisfied customer. Technically there is room to improvement to make it more user friendly and prevent bugs or issues.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

Great product. Added value to our businsess. Saving a lot of time completing owner statements. Friendly and knowledgable support team, [sensitive content hidden] are the best.

Cons:

Glitches, bugs and the fact that there is no on call number or an easy way to get personal contact. It’s not a super easy or user friendly programme.

Vanessa F.

Verified reviewer

Hospitality

2-10 employees

Used daily for more than 2 years

Review source

Reviewed November 2024

Exceptional Property Management system and Support

Unrivalled PMS with excellent support and add on features.

Ratings Breakdown

Ease of use

Value for money

Customer support

Functionality

Pros:

A comprehensive Property Management system, with extensive bolt on's. This is a very well thought out PMS with awesome tools, direct integration with Airbnb and VRBO and the option for larger property managers to add a channel manager. Brilliant accounting features, excellent owners statements and owner login features. Comprehensive marketing tools also built in as is the option to use multicurrency payments and a raft of payment gateways for guests. I have a website built and designed by their in-house design team. This has resulted in a significant number of direct bookings. The support team are fast and friendly and every user has a dedicated account manager. The recently introduced Guest App is a hit. I have been a user for 8 years and wouldn't go anywhere else.

Cons:

Only thing lacking for me is a direct integration with booking.com but this feature is coming in 2025

Showing 1 - 10 of 185 Reviews

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