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Insights on AI automation, property management best practices, and the future of hospitality

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Annual calendar view with major US events marked showing vacation rental demand spikes and revenue opportunity indicators across all four quarters
Industry Insights

Vacation Rental Events Calendar 2026: 30+ Demand Spikes

Every US event that surges rental demand in 2026-2027. Revenue estimates, prep timelines, and AI ops strategies — month by month, city by city.

Feb 22, 2026
18 min
Football stadium aerial view with surrounding vacation rental properties highlighted showing check-in and checkout flow patterns during Super Bowl weekend
Property Management

Super Bowl Rental Operations: 72-Hour Survival Guide

20 properties, $700/night, $42K weekend. From mass Friday check-in to Monday checkout chaos. AI strategies for the highest-stakes 72 hours in sports.

Feb 23, 2026
12 min
Map of United States highlighting 11 FIFA World Cup 2026 host cities with vacation rental metrics and multilingual communication indicators
Revenue Optimization

World Cup 2026 Vacation Rental Guide for Property Managers

11 host cities, 5.5M visitors, 39 match days. Pricing, multilingual AI, minimum stay strategy — everything rental managers need before June 11.

Feb 22, 2026
16 min
Split view of Las Vegas Strip, Miami skyline, and Austin Circuit of the Americas with vacation rental revenue metrics overlay
Revenue Optimization

F1 Vacation Rental Revenue: Vegas, Miami, Austin Guide

72-hour premium cycles at $600-$1,500/night. VIP guest expectations and operational strategies for all 3 US Grand Prix weekends. Revenue math inside.

Feb 21, 2026
11 min
Property manager reviewing automated AI drafts on laptop while personally handling a phone call with a property owner
Property Management

What the Top 1% of Property Managers Automate (And What They Don't)

The best property managers don't automate everything. They automate guest calls, inbox drafts, and upsell offers -- then stay stubbornly manual on maintenance, owner relations, and crisis management.

Feb 21, 2026
11 min
Southern California map highlighting Los Angeles Olympic venues with property management preparation timeline overlay
Industry Insights

LA Olympics 2028 Vacation Rental: 18-Month Prep Roadmap

Paris operators who prepared 18 months early booked out at 3x rates. Here is the LA 2028 prep roadmap that separates planners from last-minute scrapers.

Feb 20, 2026
12 min
Revenue dashboard showing upsell offer tracking across a vacation rental portfolio with early check-in, late checkout, and gap night metrics
Revenue Optimization

Vacation Rental Upselling: The Complete Revenue Playbook

470+ upsell offers sent across 130+ properties at $35-$50 each. The math, mechanics, and automation behind early check-in, late checkout, and gap night revenue.

Feb 20, 2026
13 min
Property manager reviewing guest feedback on laptop with vacation rental in background
Property Management

How to Reduce Guest Complaints in Vacation Rentals (Before They Become Reviews)

Most 1-star reviews start as unanswered questions. Learn the 5 complaint categories, which ones AI prevents (1,800+ calls handled, 6,300+ drafts), and which ones it honestly can't.

Feb 19, 2026
10 min
Property manager evaluating AI tools on a laptop with vacation rental dashboard in background
Industry Insights

AI for Vacation Rentals: The 2026 Buyer's Guide

6 categories of AI tools for vacation rentals — from voice and messaging to revenue and smart home — with real pricing, honest competitor reviews, and a framework for choosing the right stack in 2026.

Feb 18, 2026
15 min
Property manager using AI tools integrated with Guesty dashboard on laptop
AI & Technology

Best AI Tools for Guesty Users in 2026

Guesty connects your listings. These tools handle everything that happens after the booking. Dimora AI, HostAI, Duve, Akia, Breezeway, Operto — what each does, what it costs, and who it's for.

Feb 18, 2026
11 min
Desert Sol Real Estate vacation rental properties in Palm Desert, California managed with AI operations
Case Studies

Desert Sol: 6 Months with AI Operations

130+ properties. 1,800+ calls. 6,300+ inbox drafts. 470+ upsell offers. The full story of Desert Sol Real Estate's first six months running AI operations across their Coachella Valley portfolio.

Feb 18, 2026
12 min
Property manager reviewing AI-drafted guest message on laptop while guest enjoys vacation rental property
Guest Experience

How AI Improves Guest Experience Without Losing the Personal Touch

The #1 objection to AI in property management: 'Won't it feel impersonal?' Real examples from 6,300+ drafts and 1,800+ calls show how AI handles routine so PMs focus on what only they can do.

Feb 18, 2026
11 min
Property manager reviewing AI platform options on laptop with vacation rental portfolio data
Guides

How to Evaluate AI for Your Vacation Rental Business

7 questions to ask any AI vendor before you sign. A practical buyer's framework covering voice capability, PMS integration, learning systems, pricing, data ownership, implementation time, and support — plus when Dimora isn't the right fit.

Feb 18, 2026
14 min
Modern vacation rental technology dashboard showing AI operations trends and analytics
Industry Trends

Spring 2026 Vacation Rental Technology Trends

Six technology trends reshaping vacation rental operations in 2026 — AI operations layers, voice-first guest communication, automated revenue optimization, multi-agent systems, real-time learning, and payment automation. What's happening and what to do about it.

Feb 18, 2026
9 min
Property manager comparing voice AI and traditional answering service options for vacation rental operations
Comparisons

Voice AI vs Answering Services for Property Managers: The Complete Comparison

Traditional answering service, virtual assistant, call center, or AI receptionist — real pricing, real capability differences, and the honest verdict on when each makes sense for your property management operation.

Feb 18, 2026
15 min
Airbnb property management dashboard showing AI-automated guest message responses across multiple listings
Guest Communication

Airbnb Automation for Property Managers: Beyond Scheduled Messages

Scheduled messages cover 20% of guest communication. AI handles the other 80% — questions about parking, late check-in, local restaurants, pool heating. Here's how 130+ properties automated Airbnb replies.

Feb 17, 2026
12 min
Property manager automating VRBO guest messages through AI dashboard showing draft responses across multiple properties
Guest Communication

How to Automate VRBO Guest Messages with AI (2026 Guide)

Step-by-step guide to automating VRBO guest messages with AI. 6,300+ drafts generated in under 10 seconds across 130+ properties. Covers setup, VRBO-specific rules, and real results.

Feb 16, 2026
11 min
Aerial view of Palm Desert vacation rental properties near Coachella Valley with AI operations overlay showing call volume and booking metrics
Revenue Optimization

Coachella 2026: 8-Week AI Ops Guide for PMs

130+ Palm Desert properties, 15 minutes from Coachella. Week-by-week prep for 10x call volume, gap week revenue, and AI-powered guest operations.

Feb 15, 2026
14 min
Collection of VRBO guest message templates displayed on tablet and phone screens with AI personalization indicators
Property Management

VRBO Guest Message Templates That Actually Convert

12 proven VRBO message templates for check-in, complaints, upsells, and reviews. Plus how AI generates personalized versions in under 10 seconds.

Feb 15, 2026
12 min
VRBO Premier Host badge surrounded by performance metrics and AI automation indicators showing how each requirement is met
Industry Insights

VRBO Premier Host: Hit Every Metric with AI

The 5 VRBO Premier Host requirements and how AI automation locks in each one. 1,800+ calls answered, 6,300+ messages drafted, zero missed responses.

Feb 14, 2026
11 min
Split screen showing VRBO and Airbnb messaging interfaces with AI communication assistant bridging both platforms
Property Management

VRBO vs Airbnb Communication: What PMs Get Wrong

Platform-specific messaging rules, guest demographics, and response expectations compared. 6,300+ messages analyzed across VRBO and Airbnb.

Feb 13, 2026
10 min
Split screen comparison of hotel front desk and vacation rental operator working remotely
Industry Insights

Why Vacation Rentals Need Different AI Than Hotels

Hotels have front desks and staff. VR operators have themselves. The operational model is different, so the AI must be too. Here is what works for rentals.

Feb 8, 2026
9 min
Visual representation of AI knowledge base with property details, saved replies, and guest interaction data flowing into response engine
Guest Communication

AI Knowledge Bases: 85% Zero-Edit Guest Response Accuracy

Property-trained AI knowledge bases built from saved replies and PM corrections. 85% zero-edit accuracy across 6,300+ guest messages. Here is how it works.

Feb 8, 2026
9 min
Automated payment follow-up system tracking outstanding balances and recovery rates across vacation rental portfolio
Revenue Optimization

Automated Payment Follow-Up: Recover 60-70% of Balances

Stop chasing outstanding balances manually. Daily automated scans, drafted follow-ups, and escalation workflows recover 60-70% of unpaid fees. No PM effort.

Feb 8, 2026
8 min
Analytics dashboard showing automated upsell performance metrics across 130+ vacation rental properties
Revenue Optimization

Automated Upsell Results: 470+ Offers Across 130+ Units

Real data from Desert Sol in Palm Desert: 470+ early/late and gap night offers sent automatically. Acceptance rates, revenue per property, and full workflow.

Feb 8, 2026
8 min
Property manager reviewing AI-drafted messages on laptop with brand guidelines visible on screen
Guest Communication

Keep Your Brand Voice Consistent with AI Messaging

AI learns your tone from PM edits and maintains brand consistency across 6,300+ guest messages. How feedback loops keep AI on-brand. Guide inside.

Feb 8, 2026
9 min
Split dashboard showing dynamic pricing adjustments on left and operational revenue opportunities on right
Revenue Optimization

Dynamic Pricing vs Operational Revenue: You Need Both

PriceLabs optimizes nightly rates. Operational revenue captures $35-$50 upsells, gap nights, and unpaid balances. The math on why PMs need both.

Feb 8, 2026
9 min
Guest checking out late from vacation rental after accepting automated late checkout upsell offer
Revenue Optimization

Early Check-In & Late Checkout: The Upsell You're Missing

470+ automated offers at $35-$50 each. Turnaround time math, pricing strategy, and guest psychology behind the easiest upsell in vacation rentals.

Feb 8, 2026
9 min
Calendar view showing one-night gaps between reservations being automatically identified and filled through AI messaging
Revenue Optimization

Gap Night Automation: Fill Empty Calendar Nights on Autopilot

One-night gaps between bookings cannot be sold manually. See how automation identifies, messages, and fills gap nights across 130+ properties.

Feb 8, 2026
9 min
Split screen showing exhausted property manager at night versus AI interface responding instantly to guest messages
Guest Communication

5 Guest Messages AI Handles Better Than You Do

Availability lookups, property FAQs, multilingual messages, after-hours requests, and upsell offers. Why AI outperforms PMs on these 5 message types.

Feb 8, 2026
8 min
Global map with voice AI conversation bubbles in different languages connecting to vacation rental property
Voice AI

Multilingual Voice AI: 30+ Languages, Zero Extra Staff

Voice AI detects language and responds fluently in 30+ languages. Eliminate the $40,000-$60,000 cost of multilingual staffing. Tested across 1,800+ calls.

Feb 8, 2026
8 min
Payment audit dashboard showing outstanding balances flagged for automated follow-up across vacation rental portfolio
Revenue Optimization

Payment Audit Automation: Recover Every Dollar Owed

Daily automated balance scanning, follow-up drafts, and escalation workflows. Stop writing off unpaid security deposits and damage claims.

Feb 8, 2026
8 min
Revenue gap analysis showing thousands in uncaptured operational revenue across vacation rental portfolio
Revenue Optimization

The Revenue Gap: How Much Money Are PMs Leaving Behind?

Calculate missed revenue from unmade upsell offers, uncollected balances, and empty gap nights. Real math for 10, 50, and 100+ property portfolios.

Feb 8, 2026
9 min
Data visualization showing AI adoption trends in vacation rental industry
Industry Insights

State of AI in Vacation Rentals (2026): What's Working, What's Hype, What's Next

Which AI tools are property managers actually using in 2026? Adoption rates, real ROI numbers, the 6 automation categories that matter, and where the industry goes from here. Data from 210+ managed properties.

Feb 8, 2026
15 min
Property manager reviewing AI system dashboard with critical errors highlighted
Industry Insights

5 AI Adoption Mistakes STR Operators Keep Making

Most operators buy a chatbot and call it AI. Here are the 5 mistakes that lead to cancellation in 90 days -- and what actually works instead.

Feb 8, 2026
10 min
Comparison dashboard showing multiple AI tools for property management
Industry Insights

Best AI Tools for Property Managers 2026: Ranked

10 AI tools ranked by real vacation rental PMs. Honest pricing, actual limitations, no affiliate bias. Find the right fit for your portfolio size.

Feb 8, 2026
12 min
Property manager configuring voice AI settings on laptop with brand personality options and conversation examples displayed
Voice AI

Train Voice AI to Sound Like Your Best Front Desk Agent

Customize AI personality, tone, and knowledge base to match your brand. From luxury resort sophistication to beach house casual, across 1,800+ real calls.

Feb 8, 2026
9 min
Property manager reviewing AI-drafted upsell messages before sending to guests
Revenue Optimization

Upsell Messaging Templates That Convert (Not Annoy)

Copy-paste upsell templates for early check-in, late checkout, and gap nights. Offer timing psychology, channel selection, and what 470+ real offers taught us.

Feb 8, 2026
8 min
Revenue optimization dashboard showing automated upsell opportunities and gap night analysis for vacation rental properties
Revenue Optimization

Vacation Rental Revenue Optimization: The Complete Guide

Beyond nightly rates: gap nights, $35-$50 early/late checkout, payment audit automation. The revenue strategies 210+ properties use to capture hidden income.

Feb 8, 2026
18 min
Property manager reviewing VRBO messages on laptop with AI assistance panel showing platform-specific communication rules
Guest Communication

VRBO Guest Communication: AI Strategies That Actually Work

VRBO guests are not Airbnb guests. Learn who books, what they expect, and how AI handles 6,300+ VRBO messages differently than other platforms.

Feb 8, 2026
8 min
Six interconnected modules of an AI operations platform for property management
AI Technology

6 Essential Modules in an AI Operations Platform

A chatbot is not a platform. Voice AI, Inbox AI, Revenue Engine, AI Learning, Payment Audit, Dashboard -- the 6 modules that automate property management.

Feb 6, 2026
9 min
Comparison of template-based guest reply versus AI-generated contextual reply
Guest Communication

AI Drafts vs Templates: Why Templates Only Cover 40%

Templates fail on unique questions. AI reads reservation data and drafts property-specific replies in under 10 seconds. 6,300+ messages prove the difference.

Feb 6, 2026
9 min
AI guest communication workflow showing message routing through specialist agents to property manager review
Guest Communication

AI Guest Communication: The Complete PM Guide (2026)

6,300+ AI-drafted guest messages across 130+ properties. Multi-agent architecture, learning loops, and internal note drafting explained with real data.

Feb 6, 2026
18 min
Workflow showing AI draft as internal note in PMS inbox with property manager review before sending
Guest Communication

AI Drafts vs Auto-Reply: Why Draft-First Wins

Auto-reply skips your review. Internal note drafts wait for approval. After 6,300+ messages, here is why draft-first beats auto-reply on accuracy and trust.

Feb 6, 2026
9 min
Diagram showing an AI operations platform layered on top of a property management system
AI Technology

What Is an AI Operations Platform? Complete PM Guide

The 6 modules that separate an AI platform from a chatbot. How 210+ properties went from reactive firefighting to automated guest operations.

Feb 6, 2026
22 min
Timeline showing AI operations ROI milestones over 90 days
Property Management

AI Operations ROI: Week-by-Week 90-Day Breakdown

Week 1 to Week 12 benchmarks for AI operations deployment. What metrics to track, when ROI turns positive, and real results from 210+ properties.

Feb 6, 2026
9 min
Airbnb response rate metric showing 100% with AI-assisted message drafting
Guest Communication

Airbnb Response Time: Hit 100% With AI Drafting

Airbnb rewards fast replies with better search rank. See how AI keeps response times under 5 minutes across 130+ properties -- even at 2 AM.

Feb 6, 2026
8 min
Diagram showing orchestrator routing guest messages to 6 specialist AI agents
Guest Communication

Multi-Agent AI: Why 6 Specialists Beat 1 Chatbot

One chatbot fails at everything. Six specialist AI agents with mandatory tool usage deliver accurate, data-backed responses across 6,300+ guest messages.

Feb 6, 2026
9 min
Side-by-side comparison of PMS capabilities and AI operations layer capabilities
AI Technology

PMS vs AI Operations Layer: The Complete Stack for PMs

Guesty and Hospitable handle bookings. AI handles operations. Why pairing your PMS with an AI layer is how 210+ properties run the full stack.

Feb 6, 2026
9 min
Dashboard showing Voice AI call analytics including volume trends, resolution rates, and peak hours
Voice AI

7 Voice AI Call Metrics Every PM Should Track

Most PMs have zero call visibility. The 7 metrics that matter, what they reveal about operations, and how to act on data from 1,800+ analyzed calls.

Feb 6, 2026
8 min
Voice AI delivering property-specific check-in instructions to a guest over the phone
Voice AI

Voice AI Check-In: Stop Repeating Yourself 600x/Year

Check-in calls are the most repetitive PM task. Voice AI handles lockbox codes, WiFi, and parking across 130+ properties -- saving 40+ hours per year.

Feb 6, 2026
8 min
Diagram showing Voice AI pulling real-time reservation data from a PMS during a guest phone call
Voice AI

Voice AI + PMS Data: How Calls Get Resolved in Seconds

Voice AI pulls live reservation data to resolve lockouts, give directions, and quote availability. Not speech recognition -- full PMS context in real time.

Feb 6, 2026
8 min
Voice AI system connected to property management software resolving a guest call in real time
Voice AI

Voice AI for Vacation Rentals: The Complete 2026 Guide

How Voice AI works, what it handles, and when it escalates. Real numbers from 1,800+ calls across 130+ properties. Everything PMs need to know.

Feb 6, 2026
16 min
Side-by-side comparison of an IVR phone tree versus a Voice AI conversation flow
Voice AI

Voice AI vs IVR: Why PMs Are Ditching Phone Trees

IVR phone trees frustrate guests and still need humans. Voice AI resolves calls in 60-90 seconds with live reservation data. See why PMs are switching.

Feb 6, 2026
8 min
Futuristic property management dashboard showing AI-powered operations
Industry Trends

AI-First Property Management: The 2026 Shift

Why early-adopter PMs already handle 1,800+ calls and 6,300+ messages with AI. The operational model is changing. Here is what AI-first looks like in practice.

Oct 1, 2025
9 min
Florida property manager reviewing positive results on tablet by the pool
Industry Trends

Case Study: 100+ Calls/Week Handled by AI Receptionist

A 35-property vacation rental portfolio cut call handling to zero. Exact numbers on calls handled, hours saved, and revenue gained. Full breakdown inside.

Sep 5, 2025
8 min
Property manager relaxing with family while AI handles evening calls
Property Management

After-Hours Calls: 3 Ways to Cover 24/7 Without Burnout

67% of guest calls come after 6 PM. Stop sacrificing sleep and family time. Three proven coverage models ranked by cost, quality, and PM sanity.

Aug 12, 2025
7 min
Automated workflow diagram showing seamless property management operations
Property Management

Property Management Workflow Automation: Save 20+ Hours/Week

How 210+ properties automate booking inquiries, maintenance, and guest comms. Step-by-step workflow guide with real time savings from production operations.

Jul 25, 2025
10 min
Happy guests receiving instant automated responses on their phones
Guest Experience

5 Guest Experience Automations That Drive 5-Star Reviews

Practical automations used across 210+ properties to boost reviews. From instant check-in answers to proactive upsells. No extra workload required.

Jul 8, 2025
8 min
Side-by-side comparison of AI receptionist vs human receptionist capabilities
AI Technology

AI vs. Human Receptionists: Honest Cost and Quality Comparison

1,800+ calls handled by AI vs human answering services. Side-by-side on cost, accuracy, and 24/7 coverage. Real data, not theory.

Jun 20, 2025
9 min
Calculator showing lost revenue from missed property management calls
Property Management

Missed Calls Cost PMs $287 Each: Here's the Math

Every unanswered call costs $287 in lost bookings. Calculate your total missed revenue from voicemails and slow response times with our formula.

Jun 3, 2025
8 min
Property manager relaxing with family knowing AI handles all calls 24/7
Property Management

Peace of Mind for PMs: AI That Handles the 2 AM Call

1,800+ guest calls answered without a single missed one. No more 2 AM lockout panic, no more dinner interruptions. How AI restores work-life balance for PMs.

May 15, 2025
7 min

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