Vacation Rental, Small Hotel & Guest House Marketing | AI for Hospitality Smart Pineapple

Dynamic Pricing with AI for Small Properties

Think dynamic pricing is just for big hotels with fancy tech? Think again—this post shows how small rentals and inns can use AI to price smarter, stress less, and stay booked.

Canadian Travel to the U.S. Is Down: What It Means for the Hospitality Industry

Canadian travel to the U.S. is seeing a steep decline—and it’s hitting border states and tourism-driven businesses hard. This article breaks down what’s happening, why it matters, and how hospitality pros can pivot their marketing to reach the travelers who still plan to visit.

Real Talk for Hosts: My Chat with Host Planet 🎙️

Learn how STR hosts can use AI to streamline marketing, write better prompts, and create content faster—without losing the human touch. As I chat with Host Planet!

Have You Got: Smarter Leads for Professional Property Managers

Have You Got helps property managers get better bookings without new calendars, extra inboxes, or platform fees. Just leads that fit — and a process that works with your day-to-day, not against it.

Airbnb Just Got Hotel-Savvy

Airbnb just linked HotelTonight to its platform—giving hotel guests Airbnb credit and quietly launching its first loyalty play. This move could shift traveler habits and competition, making it a moment small hotels and STR owners shouldn’t ignore.

Click, Book, Smile: 5 Guest-Winning Strategies

Looking for simple ways to keep guests happier and boost bookings? These five digital strategies are easy to implement and can make a big impact on guest experience—without adding to your workload.

AI Prompt to Find Current STR Regulations

Staying compliant with short-term rental regulations can be overwhelming, but AI can simplify the process. Use this ready-to-go AI prompt to quickly find up-to-date licensing, zoning, tax, and compliance rules for your specific location.

Overseasinfo.tv "Tourist Information Platform of the Year"

Overseasinfo.tv was recently named “Tourist Information Platform of the Year” for its community-driven approach to travel planning. With video-based reviews and an AI chatbot that offers personalized recommendations, it’s making it easier for travelers to discover and plan their trips.

Chatting About AI with Indira Ramgarib Katwaroo

AI is transforming the travel industry, helping advisors streamline itinerary planning, improve customer service, and refine marketing strategies. As a guest on Travel Talk with Indira, I discuss with Indira Ramgarib-Katwaroo how AI enhances—rather than replaces—travel advisors, making their work more efficient and impactful.

Social Media Hacks for Hospitality: The Bold Moves You’re NOT Making (But Should Be!) 🔥

Your social media strategy might be holding you back—but a few bold moves can change everything. From Instagram carousels to TikTok trends, here’s how hospitality pros can turn social media into a booking machine (without wasting hours online).

Personalization Matters in Hospitality

Personalization is key in hospitality, but it can be time-consuming—AI makes it effortless. Learn how to generate custom guest itineraries in seconds using AI.

How to Improve Your Airbnb Listing Quality and Increase Bookings

Mastering Airbnb’s new quality standards is the key to securing more guests, better reviews, and making sure your listing doesn’t get buried—or worse, removed entirely!

How to Get Last-Minute Reservations: Try These Booking Hacks

Wondering how to get last-minute reservations before Winter-Spring Break? These booking hacks will help hotels and vacation rentals fill rooms fast with smart pricing, targeted marketing, and guest incentives that drive quick bookings.

Attract More Guests with Better Website Content

AI is reshaping search, but on-site SEO remains essential for attracting guests and driving direct bookings. Optimizing your website with clear, guest-focused content ensures your hospitality business stays visible and competitive.

AI for Hospitality: ChatGPT Takes Over Your To-Do List

ChatGPT's AI for Hospitality Scheduled Tasks feature is like having a personal assistant who never sleeps, automating your guest communication, daily operations, and even marketing campaigns with ease. Say goodbye to juggling tasks and hello to more time for delighting guests and growing your business!

Why Your Vacation Rental Needs to Talk Back (Literally!)

Imagine guests saying, “Hey Alexa, dim the lights!” and your rental becoming their favorite stay ever. Voice tech isn’t just cool—it’s your secret weapon to crush the competition.

Is Your Rental in Shape for 2025?

The 2025 short-term rental market is stabilizing, with rising occupancy rates, shifting guest preferences, and increasing demand for unique, personalized stays. By leveraging AI for pricing, guest communication, and sustainability, hosts can adapt to evolving trends, meet traveler expectations, and position their properties for long-term success.

The Future Is Booked: What 2025 Holds for Vacation Rentals

In 2025, niche vacation rental platforms are redefining how properties connect with the right guests. These platforms focus on STRs offering unique experiences, targeted audiences, and meaningful stays, helping your property stand out in a crowded market.

From Rain to Reservations: How Weather and Events Drive Local Hospitality SEO Searches

Hospitality SEO: Optimize Your Booking Engine for SEO and Guests

Your booking engine isn’t just for reservations—it’s your ticket to topping search results and winning over guests. With smart Hospitality SEO strategies, you can rank higher, book faster, and keep guests coming back for more.

Feeling the Slow Season Blues?

Winter bookings feeling slow? Try these six simple strategies to make your property the cozy, can’t-miss spot travelers are searching for this season.

Hospitality SEO Tips: Micro-Moments Boost Bookings

What if you could turn every guest search into a guaranteed booking? Get hospitality SEO hacks and unlock the secret to micro-moment domination.

The Hospitality Web We Weave: Building Stronger Guest Connections

The hospitality web is a delicate but powerful creation, spun from the threads of digital presence, guest trust, and emerging tech. Master this weave, and you’ll turn curious browsers into loyal guests.

Booking.com’s New Review Scores: What You Need to Know

Booking.com’s updated review scores focus on what matters now—your recent efforts. Discover how AI tools can make managing feedback easier and more effective.

Airbnb 2025, What Every Vacation Rental Owner Needs to Know

Airbnb is shaking things up with its 2025 plan, going way beyond short-term rentals. Here’s how it could boost—or challenge—your vacation rental game.

Redefining Hotel Stays in 2025 | Seamless, Personal Guest Experiences

By 2025, artificial intelligence will change hospitality forever. Offering guests personalized, seamless stays, streamlining hotel operations. From customized room settings to quick check-ins and AI-powered service. The future of hotels is all about effortless comfort and innovation.

Vermont: Guest Experience + Community Thrive

Vermont knows how to do hosting right. Passionate property owners and industry leaders make up the Vermont Short Term Rental Association (VTSTRA). I’m thrilled that Smart Pineapple is now part of a community that’s setting the bar for guest experiences and collaboration.

Guest Mishaps Don’t Have to Be a Budget Nightmare

Dealing with guest damages in vacation rentals can get expensive. Simple tricks like choosing durable items and adding damage waivers make it way easier to handle. You can cover costs, keep your guests happy, and run a smooth, stress-free rental business.

AI-Powered Snaps: Hospitality Photo Hacks That Click

Your smartphone, supercharged with AI, can transform dull property shots into guest-luring masterpieces. Master lighting, composition, and editing for photos that demand attention.

The Power of Price Dynamic Tips to Drive More Bookings

Want to make the most out of every booking? Dynamic pricing uses AI to set the right rate at the right time, helping vacation rentals attract guests, increase revenue, and stay ahead of the competition.

Consumer Surveys Tell-All: The Secrets Small Hotels Need to Know!

Consumer surveys remind us as hospitality pros to keep it real and lean into our strengths. Focus on what makes your property unique, connect authentically with guests, and use tips to win over the competition.

Look Who’s in the Top 30 – Yep, That’s Us!

Smart Pineapple just landed on The Silicon Review’s Top 30 Innovators list! With AI tools that make guest engagement and content easy, they're helping small hospitality businesses grow sustainably and stay ahead.

AI and No Headache: How Small Properties Can Win Big

Wondering if AI is too complicated or expensive for your small property? With the right tools, you can overcome tech fears, streamline operations, and boost guest satisfaction—AI isn’t here to replace the human touch, but to enhance it.

Simple Metrics for Small Hotels

Small hotels have more potential than meets the eye—when every space and guest interaction works smarter, profits grow. Discover easy ways to track what truly matters, boost revenue, and create experiences guests will rave about.

The Lazy Hotelier's Guide to Blogging

Blogging’s like giving your guests a sneak peek behind the curtain – it builds trust, boosts bookings, and keeps your place in the spotlight. Think of it as the ultimate guest magnet with a personality!

Your Homepage Is Your Property’s Welcome Mat

Creating a homepage that really speaks to guests is tough. Balancing property features, telling your story, and getting visitors to book can feel like a lot! Four quick musts for a homepage that works.

Hotel Marketing: TikTok Isn't Just for Dance Challenges

TikTok isn’t just for wild crazes; it’s a fun way to show off your property and connect with travelers. Check out how creative content, influencer collabs, and guest engagement can boost your bookings!

Why TikTok Can't Be Ignored, (Even If You Want To)

TikTok is redefining travel marketing, even for those hesitant to jump in. It's about engaging conversations, staying on top of trends, and leveraging tools like Search Ads Campaign to connect with today’s travelers.

Whats it gonna be? Expedia or Booking.com?

Not sure whether to list your rental on Expedia or Booking.com? We’ve got the breakdown on what makes each platform tick, so you can pick the best fit for your property!

How to Achieve Airbnb Success in 2025

Want to nail Airbnb success in 2025? It’s all about great photos, smart pricing, solid reviews, and adding those personal touches that make guests feel right at home.

Grab a Coffee and Master Dynamic Pricing in 15 Minutes

Grab a coffee and spend 15 minutes learning dynamic pricing tips from Ryan Saylor, at Beyond. Five expert strategies to help short-term rental owners hosted by our friends at Holiday Cottage Handbook.

Is Your A$$ Covered as a Property Owner?

Airbnb AirCover offers $3M in damage coverage and $1M in liability insurance, but claims can be slow, and some damages might not be covered. It's free, but keeping personal insurance is still smart for full protection.

James Varley: The Short-Term Rental Superhero

James Varley from Holiday Cottage Handbook, who's on a mission to bridge the gap between short- and long-term rentals. His podcast and resources are like a treasure map for vacation rental success—don't miss out!

Vacation Rental Business Myths - BUSTED!

Running a vacation rental isn't just a hobby—it's a full-fledged business, and it's time to start treating it like one. 10 Myths you may be telling yourself.

Keep Your Calendar Hot: Clever Marketing Hacks for Fall, Winter, + Beyond!

When fall hits and bookings dip, it’s time to spice up your marketing game! From cozy winter deals to sizzling summer promos, these tips will fill your calendar no matter the season.

Best Channel Managers for Hotels & Rentals Made Easy

The right channel manager helps manage bookings, avoid double bookings and keeps everything in sync. Make it a breeze to handle multiple booking sites. Focus on giving guests a great experience while staying organized.

Hospitality Marketing Essentials - It's All About the Numbers

Simple data and key numbers can transform your hospitality business. From setting up Google Analytics to tracking essential metrics, these easy steps will sharpen your marketing strategy and boost results.

Transforming the Way You Connect with Guests

Wondering how AI is changing hospitality? Kay Walten of Smart Pineapple chats with Sebastian Munoz about how it's reshaping guest connections!

Curious How Virtual Tours Can Boost Your Bookings? Let’s Find Out!

Virtual tours and immersive content offer small hoteliers and vacation rental owners a great way to connect with guests, showing off their property and local attractions before they even arrive, which is a key part of hospitality marketing essentials.

Boost Staff Happiness + Guest Experience with Tip & Go's Cashless Tipping

Tip & Go, a simple yet powerful tool that can truly transform how you support your staff and delight your guests. If you’re passionate about improving both employee satisfaction and guest experience, this might be the perfect solution for your hotel.

Vacation Rental Marketing: Choosing Between Airbnb and Vrbo

Think your property is listed in the best spot? The truth might surprise you—see if you're listing is hitting your ideal guests

Partners in Small Hotel Marketing Tools and Vacation Rental Success

Inn Style’s new partnership brings innovative tools and fresh opportunities to small hotels and vacation rentals. With a focus on simplicity and support, they’re helping businesses thrive in a competitive market.

Boutique Hotel & Vacation Rental Marketing Essentials - Paid Ads Part 2

If you're looking to quickly boost your property's visibility and attract more guests, you'll discover practical steps to master Google Ads, retargeting, social media advertising, and metasearch strategies.

Boutique Hotel & Vacation Rental Marketing Essentials - Paid Advertising

If your eyes cross just thinking about paid online advertising, this post is for you. Learn the basics with easy steps, useful resources, and practical tips tailored for beginners in digital marketing.

Do You Really Know How to Reach Gen Z and Boomers?

When you know what drives Gen Z and Boomers, marketing becomes more meaningful. Speak to their unique preferences, and you’ll naturally build stronger, lasting guest relationships.

Online Learning - Marketing Tools for Small Hotels + Vacation Rentals

Success in hospitality is a shared journey. Our online community on Skool empowers hotel and vacation rental professionals with tools, insights, and support to help you grow.

Boutique Hotel & Vacation Rental Marketing Essentials - Online Reviews

Are your online reviews hurting your hospitality business? Learn simple steps to turn every review—good or bad—into an opportunity, and understand why it matters.

Marketing for Vacation Rentals and Small Hotels in a Shifting Market

The lodging market is shifting, but there's no need to despair. Small hotels and vacation rentals can confidently navigate these changes by using smart marketing tools. Embrace your unique strengths, such as flexibility and personalized experiences, and you can continue to attract guests and thrive, even in uncertain times.

Vacation Rental Marketing: Smart Pineapple Joins VRMA

Smart Pineapple is now a proud member of VRMA, connecting us with top vacation rental marketing resources. We're excited to share these insights to help you succeed.

Boutique Hotel & Vacation Rental Marketing Essentials - OTA's & Metasearch Part 2

How metasearch engines and OTAs influence guest booking behaviors, offering insights to help you refine your marketing strategies? By understanding these platforms, you can better tailor your online presence, ensuring it meets the diverse needs of travelers while enhancing your property's visibility.

Boutique Hotel & Vacation Rental Marketing Essentials - OTA's & Metasearch

OTAs and metasearch engines should be part of your booking strategy. Learn practical tips on listing your property, managing profiles, and using channel managers for better efficiency.

Boutique Hotel & Vacation Rental Marketing Essentials - Facebook

Timing is crucial for Facebook posts to maximize engagement. Posting between 8 a.m. and noon on Tuesdays and Thursdays, along with analyzing audience data, can significantly improve reach.

Boutique Hotel & Vacation Rental Marketing Essentials - Content Marketing

Are you getting the most out of content marketing? Boost your property's bookings by using content marketing to build trust and engage guests. Discover essential tips to position your property as a top choice for travelers.

Chill Work in Hospitality Tech An Innovative Approach

Redefine work culture in hospitality tech by focusing on balance, trust, and long-term relationships. Inspired by SparkToro's Chill Work Manifesto, we prioritize employee well-being and sustainable growth.

Hospitality Marketing Essentials: Spike-Up Your Online Presence with SEO

Are you leveraging SEO to boost your small hotel or vacation rental's online presence? This guide covers keyword research, local content creation, optimizing your Google Business Profile, and more, helping you attract more guests and improve your digital marketing efforts.

Boutique Hotel & Vacation Rental Marketing Essentials - Email

Email marketing keeps you connected with past guests and boosts repeat bookings for boutique hotels and vacation rentals. Discover how to build your email list, personalize campaigns, and automate follow-ups for effective results.

Vacation Rental & Hotel Marketing Essentials: Building a Strong Online Presence

Learn essential strategies for boosting your vacation rental or hotel's online presence in this post from our Hospitality Marketing Essentials series. Tips on captivating guests with high-quality visuals, clear information, and effective SEO to drive more direct bookings.

Do You Need a Hotel Marketing Agency?

Deciding if your property should hire a hotel marketing firm or build an in-house team can be tough. This post helps you understand the benefits of each to make the best choice for your hotel.

Turn Events into Bookings

Boost your bookings and support the local economy by leveraging local events. Stay updated on upcoming events, adjust your pricing, and highlight these events in your listings to attract more guests.

Generative AI in Boutique Hotel Marketing

Boutique hotels can leverage AI in their marketing strategies to boost bookings and up-level guest experiences. AI marketing in key areas like personalization, predictive analytics, content creation, customer journeys, and SEO, offering innovative tactics to stay competitive.

Vacation Rental & Hotel Marketing: Tips for More Bookings

Get practical vacation rental marketing strategies to boost direct bookings and enhance guest experiences. Learn how to optimize your website design, leverage SEO and social media, and implement personalized guest interactions and loyalty programs.

New Booking.com Policies: What You Need to Know

Booking.com’s discontinuation of prepayment policies for Europe may lead to more cancellations, cash flow disruptions, and rate parity concerns. Hoteliers and vacation rental owners need to adapt by investing in direct booking strategies, improving operational processes, and strengthening customer relationships.

Storming Innovation For Guests

Imagine boosting your bookings and making guests happy, rain or shine. WeatherPromise has got your guests covered with travel insurance that ensures their vacation investment is safe, no matter the weather.

No Passport Required: Your Best Guests Don't Need a Passport

There may be a hidden goldmine in your own backyard—local travelers! Charm them with tailored experiences, special packages and watch your business thrive. AI-powered marketing makes it easy. No passport is required for this adventure!

Hospitality + Tourism 2024: McKinsey & Co. Insights

McKinsey & Company's report reveals key insights for boosting business with simple, cost-effective strategies. Focus on short term rental marketing by tapping into local travel, personalization, off-season deals, and social media to thrive in 2024.

What Virtues is Your Property Listing Signaling?

Find out how showcasing your property's best qualities can boost your earnings and attract more guests. Learn the sweet spot between highlighting your virtues and going overboard, so you can build trust and avoid turning off potential visitors.

Boosting Business in the Tourist Economy

Turbocharge your tourist economy game! Tap into the latest Travel & Tourism Development Index 2024 insights—click for the latest trends

Going the Distance: Embracing Sustainable Tourism's Long Run

Ready to sprint towards a more sustainable future for your business? Sustainable tourism can set the pace for attracting eco-conscious travelers and boosting guest satisfaction. Get easy, actionable tips and future trends.

Are There Holes In Your Bucket? Keep Tourism Dollars Local

Want to make your business and community thrive? Find out how keeping tourist dollars local can boost your profits and support the local economy with simple, effective tips!

Making Waves with AI in Hospitality – As Seen in Travel and Hospitality Tech Outlook

We're excited to be featured in Travel and Hospitality Tech Outlook!

How to Boost Direct Bookings and Reduce OTA Fees

Want to save money on OTA commissions? Boost your profits by shifting to direct bookings. Learn tactics to gain greater independence and financial advantage.

Blogging Takes Too Long, Until Now!

Discover how to transform blogging from a time-intensive chore to a powerful marketing tool in just a few minutes with Smart Pineapple. Understand how blogging works, practical steps to quickly launch a blog, enhance engagement, and boost bookings, demonstrating that effective blogging doesn't have to be time-consuming.

Boost Bookings: Short-Term Rentals and Tour Operators

There are advantages of short-term rental marketing by partnering with tour operators. Craft travel packages that include unique accommodations, emphasizing how such partnerships can extend market reach, enhance guest experiences, and increase bookings.

Tourism Education with AI: Highlights from Cape Town's Workshop

Insights from the Think Tank workshop held in Cape Town on April 2nd, 2024, where 60 teachers gathered to explore the integration of AI in tourism education.

Smart Pineapple Shines at WTM Africa 2024

Just got back from an unforgettable week at WTM Africa 2024 in Cape Town! It was buzzing as Smart Pineapple made its big debut with some game-changing AI tools. We are teaming up with Swartland Tourism for a cool project, chatted up potential partners like Weeva Earth and Nightsbridge. Can't wait to share more as we keep pushing the boundaries in travel tech! Stay tuned!

AI in Travel & Hotel Marketing: Enhancing, Not Replacing, the Human Touch

AI can streamline and customize travel, it won't overshadow the crucial human element essential for meaningful exploration. It showcases expert insights and practical uses of AI in travel, illustrating its function as an enhancer of, not a replacement for, the rich personal experiences that make travel unforgettable.

Increase Your Guest House's Bookings Selecting the Right Social Media Channels

Boost your bookings with selecting the ideal social media channels. Perfect for owners and managers of guest houses.

Guest House Marketing: Boost Direct Bookings Mastering Descriptions

Explore the power of property descriptions in attracting ideal guests, managing expectations, standing out, and boosting bookings.

How to Market Your Guest House: Tips for More Bookings

Get essential strategies for guesthouse owners to enhance their digital presence and secure more direct bookings, including optimizing website design, leveraging SEO, social media engagement, and creating personalized guest experiences. Discover practical tactics to outshine competitors and cultivate guest loyalty in the competitive hospitality market.

AI in Hotel & Guest House Management: Boosting Efficiency & Guest Experience

In the modern hospitality sector, AI offers transformative solutions for small hotels. Tools like Smart Pineapple streamline operations, enhance guest experiences, and boost loyalty, making AI adoption essential for staying competitive.

Beyond Guest House Booking Systems: Next-Gen Guest House Marketing

Dive into the future of guest house management, where innovative marketing strategies are transforming guest experiences and driving bookings.

Pocket-Friendly Strategies to Turbocharge Your Guest House Marketing

Discover effective, budget-friendly marketing strategies for boutique hotels at Smart Pineapple. Harness social media power, enhance SEO, and improve user experience.

AI Guest House Marketing: Elevate Your Bookings Now!

Discover AI's impact on hospitality marketing. Learn how it streamlines operations and personalizes guest experiences with Smart Pineapple.

A Global Perspective of the "Boutique Hotel"

Uncover the magic of boutique hotels, where AI marketing tools for travel redefine your journey. Explore how personalized luxury and local charm merge to create unparalleled experiences.

Leveraging the Power of Blogging for Vacation Rental Owners

Discover how blogging can boost your vacation rental & guest house business. Enhance credibility, improve SEO, and engage guests. Start a blog to propel your success

Guest House AI Marketing: Make Your Property the Talk of the Town

Explore cutting-edge Vacation Rental AI Marketing Tools designed to elevate guest experiences. Harness AI to personalize stays, optimize marketing, and drive bookings for your vacation rental.

The Art of Meta Descriptions

Master the art of meta descriptions. Boost your site's click-through rates and make a memorable first impression.

Navigating the Buyer's Journey

Embark on a marketing road trip! Explore the buyer's journey from awareness to retention and learn to guide your customers booking.

Avoid the "Copy-Paste" Trap

Discover the pitfalls of duplicate content on vacation booking sites and how unique, quality content enhances the booking experience.

The Content Calendar: A Hospitality Hero's Secret Weapon!

Discover the content calendar, the secret weapon in hospitality and vacation rental businesses. Boost engagement and revenue. Read more!

One day... or Day 1?

Start getting hours back in your schedule with our tools today.

Get Started Now

Book a free live walk-through with us

We want to you succeed. Sign up for our app and get 30-days free. Then let's walk-through your needs together.

This is who we are

We are a woman-owned business that is passionate about building hospitality and tourism worldwide. We believe in local economies, education and professional development. Smart Pineapple, a brand of Pineapple Innovate Inc.