How I Transformed a Basic Hostaway Booking Engine Into a High-End, API-Powered Direct Booking Website

Squarespace + Hostaway API integration using a custom Cloudflare Worker — Case Study

If you're a vacation rental owner or property manager using Hostaway, you’ve probably wondered how to build a high-end direct booking website without giving up the convenience of your PMS… Hostaway’s built-in booking engine works — but it offers limited branding, no SEO structure, and almost no control over design.

In this case study, I’ll walk you through how I transformed Hayward Rentals’ basic Hostaway booking engine into a premium, dynamic, API-powered direct booking site built on Squarespace. Using a custom Cloudflare Worker to securely integrate the Hostaway API, I created automated property listings, lake-specific SEO landing pages, and a fully branded booking flow that helps this 40+ property portfolio increase direct bookings and reduce OTA dependence.

Table of Contents

If you’ve ever used Hostaway’s built-in booking engine as your main website, you know the feeling… It works. It syncs. It books.

But from a design, branding, and guest-experience perspective?
…it’s extremely basic.

That’s where Hayward Rentals was before Dustin and I began working together.

Dustin manages more than 40 beautiful cabins and lake homes in one of Wisconsin’s wealthiest and most scenic vacation regions — but online, his brand was reduced to Hostaway’s default layout.

There was no high-end feel.
No storytelling.
No powerful first impression.
No SEO architecture.

Just a functional booking tool.

A portfolio of this quality deserved so much more.

The Goals (A Clear Vision for an Elevated Direct Booking Experience)

Creating a high-performing direct booking website for a vacation rental brand requires far more than a pretty design. It needs automation, real-time accuracy, and a structure that actually supports SEO. When Hayward Rentals came to me, their online presence was limited to the default Hostaway booking engine — functional for reservations, but not designed for branding, visibility, or growth.

To compete in a high-demand lakes region and attract guests searching for terms like “Round Lake cabin rentals” or “Tiger Cat Lake vacation homes,” they needed a website built for trust, speed, and search.

Below are the core goals we set for transforming their basic setup into a premium, API-powered, SEO-optimized direct booking experience that reflects the quality of their 40+ properties — and gives them a scalable foundation for long-term growth.

1. A high-end, custom-branded website

Something that matched the quality of his properties and his newly redesigned logo.
Something luxurious, local, and trustworthy.

2. Dynamic listing pages that update automatically

No manually creating or editing 40+ property pages.
No outdated info.
Everything pulled straight from Hostaway.

3. Lake-specific landing pages

Round Lake. Tiger Cat Lake. Moose Lake.
These would serve both SEO and guest navigation.

4. A frictionless direct booking flow

Guests should go from browsing → choosing → booking without ever feeling confused.

5. Additional SEO-friendly content pages

Local events, lake guides, and things-to-do pages to grow organic traffic year-round.

But there was one big obstacle…

The Technical Challenge: Squarespace Doesn’t Support PMS API Integrations

One of the biggest hurdles in building a direct booking website with dynamic property listings is the fact that Squarespace does not support secure API integrations for vacation rental PMS platforms like Hostaway.

Unlike WordPress or custom-coded sites, Squarespace cannot store encrypted API keys, run server-side code, or make authenticated calls to the Hostaway API. This means you can’t natively pull real-time availability, pricing, amenities, or property details into a Squarespace site — at least not without exposing sensitive data in the browser.

For most property managers, this limitation forces them to rely entirely on the default Hostaway booking engine, which offers minimal branding, no dynamic pages, and almost zero SEO value.

To overcome this, I engineered a custom solution: a Cloudflare Worker that acts as a secure, server-side bridge between Squarespace and the Hostaway API. This workaround allowed us to safely store API keys, fetch and transform property data, and deliver optimized JSON to Squarespace — making features like automated listings, lake-specific pages, and real-time updates possible on a platform that technically shouldn’t support them.

The Breakthrough: A Custom Cloudflare Worker

To create dynamic property listings and real-time availability on Squarespace, we needed a way to communicate securely with the Hostaway API — something Squarespace doesn’t support natively. This is where the custom Cloudflare Worker became the backbone of the entire system.

A Cloudflare Worker functions as a lightweight, serverless API layer. Instead of exposing API keys in the browser (which would break Hostaway’s security requirements), the Worker stores all credentials on Cloudflare’s secure edge network. It then performs authenticated requests to the Hostaway API, fetches property data, formats it, and returns clean, optimized JSON to the Squarespace frontend.

This single piece of architecture unlocked everything that makes a high-end, automated direct booking website possible:

• Secure API key storage

• Real-time availability + pricing pulled from Hostaway

• Dynamic property listings that update automatically

• Filtering by lake/area for SEO-friendly landing pages

• Optimized images and payloads for fast load times

• Zero exposure of sensitive PMS data in the browser

• …and a few extra features like: vacation rental schema, image compression, etc.

With this setup, Squarespace behaves almost like a custom-coded platform — able to display accurate, synced, live property information across 40+ listings. The Cloudflare Worker essentially transforms a static website builder into a powerful, API-driven vacation rental website, without sacrificing design, speed, or ease of management.

This custom integration is the core reason Hayward Rentals now has a premium, automated, scalable direct booking system that far surpasses what the default Hostaway booking engine can do.

With this in place, Squarespace behaves as if it has native Hostaway integration.

This opened the door to the dynamic functionality Dustin needed.

Step 1 — Design Foundation: Elevating the Brand with Wildwood, my Squarespace Vacation Rental Template

Before any API integration or technical work could begin, we needed a website foundation that matched the quality of Hayward Rentals’ properties. Dustin’s previous setup—the default Hostaway booking engine—was functional but visually bare. It didn’t convey the high-end, lakeside experience guests expect in this region. And from an SEO perspective, it offered no structure for ranking, no content hierarchy, and no opportunity to build trust.

So the first step was choosing a design framework that felt elevated from the very first click.

I built the new website on top of my Wildwood Squarespace template, a premium template designed specifically for vacation rental brands that need a more luxurious, modern, and editorial feel. Wildwood already incorporates the kind of typography, spacing, and warm, organic styling that resonates with the “cabin luxe” aesthetic of high-quality lake homes. The moment Dustin saw it, he immediately connected with the fonts, the color palette, and the calm, upscale energy.

This meant we didn't need to reinvent the design—just customize and expand Wildwood into a full direct-booking ecosystem. Keeping the existing aesthetic allowed us to:

• maintain strong brand consistency

• ensure a polished, high-end look from day one

• create a professional visual identity around his new logo

• build trust with potential guests instantly

• stay focused on the backend API features without sacrificing UX

Starting with Wildwood gave us a beautiful, strategic foundation. The next steps would turn it from a template… into a dynamic, data-powered, SEO-optimized direct booking website that finally represented the true quality of Hayward Rentals.

If Wildwoods isn’t your vibe, I have a few more premium vacation rental templates to choose from…

Want to learn more about vacation rental branding? Read also…

• How Vacation Rental Branding Can 3x Your Bookings (Even If Your Property Is Basic)

Step 2 — Building Automated, Dynamic Property Listings With the Hostaway API

Once the visual foundation was in place, the next challenge was creating a listings system that didn’t just look beautiful—but actually worked like a modern, data-powered vacation rental website.

Hayward Rentals manages more than 40 cabins and lake homes, which means one thing: manually updating property pages is not just unrealistic—it's impossible. Dustin needed a website that could sync with Hostaway behind the scenes and always display accurate, up-to-date information without touching a single field in Squarespace.

This is where the custom Cloudflare Worker + Hostaway API integration became the core engine of the project.

Using the Worker as our secure server-side layer, we were able to fetch live property data directly from the Hostaway API and feed it into Squarespace dynamically. That allowed us to create automated listing pages that update themselves whenever Dustin changes something in Hostaway — including:

• property names and descriptions

• number of guests, bedrooms, and bathrooms

• photos and galleries

• amenities

• custom fields like lake/area

• pricing snapshots

• availability previews

From an SEO perspective, this was huge.

Instead of static pages that quickly become outdated, the website now has:

• fresh, accurate content that changes in real time

• structured property data Google can crawl

• unique landing pages tied to local search intent

• fast-loading images optimized through Cloudflare

• dynamic internal linking that strengthens site architecture

From a user experience perspective, it’s a game changer.

Guests can browse properties with the confidence that everything is current—and that trust directly impacts bookings.

The best part?

Dustin never has to manually update the website.
He manages everything inside Hostaway, and the website reflects those changes automatically.

This step turned Wildwood from a beautiful template into a living, breathing direct booking system powered by real-time vacation rental data.

Next, it was time to make those listings even more useful—with lake-specific landing pages designed for both SEO and guest navigation.

A Note on Single Property Pages: Custom Template + Precision Styling

Behind each dynamic listing is a single property template page I built specifically for Hayward Rentals. Instead of relying on Squarespace’s native page layouts (which aren’t designed for API-driven content), I created a custom template section where every property is rendered using the same structured design—then populated automatically with Hostaway data. This ensures consistency in layout, spacing, buttons, galleries, and accessibility across all 40+ properties.

To elevate the presentation even further, I added custom CSS styling tailored to the Wildwood aesthetic: refined typography, polished spacing, elevated photo layouts, responsive grids, lake-badge styling, and enhanced mobile readability. This gives each property page an editorial, high-end feel—far from the generic, utilitarian look of default PMS pages. Every page feels handcrafted, even though the data is fully automated.

This blend of template engineering + custom CSS is what makes the entire experience feel premium, consistent, and designed—rather than assembled from disconnected PMS fields.

Step 3 — Creating Lake-Specific Landing Pages for Powerful Vacation Rental SEO

With automated listings in place, the next step was turning Hayward Rentals’ biggest geographical advantage into an SEO engine: the lakes themselves.

The Hayward region is defined by its lakes—Round Lake, Tiger Cat Lake, Moose Lake, and dozens more. Guests don’t just search for “Hayward cabins.” They search for:

• “Round Lake cabin rentals”

• “Tiger Cat Lake vacation homes”

• “Moose Lake cabin rentals”

• “cabins near Hayward Wisconsin lakes”

These are high-intent, location-based searches that lead directly to bookings.
But on the old Hostaway booking engine, there was no way to create individual pages for each lake, no way to highlight specific areas, and no way to rank for these valuable keywords.

Using the data provided by the Hostaway API, we added a custom field for area (ex: “Round Lake”), and then built dynamic lake-specific pages that automatically filter properties by that location.

Each page now:

• displays only the properties located on that lake

• uses dynamic data pulled directly from Hostaway

• updates automatically when new listings are added

• targets exact keywords guests are searching for

• gives Google clear signals about local relevance

• helps guests quickly find the type of stay they want

This structure does two critical things:

1. It dramatically improves SEO.

Google loves structured, location-based content.
These pages give the site dozens of new indexing opportunities that the Hostaway booking engine simply can’t create.

2. It improves the guest experience.

If a family wants to stay on Round Lake, they can instantly see every property on Round Lake.
No scrolling.
No filtering.
No frustration.

It turns the website into a local “insider guide” rather than just a list of rentals.

This step was the turning point where the project stopped being just a “better website” and became a strategic, SEO-driven direct booking platform with hyper-targeted landing pages designed to capture organic traffic and convert it effortlessly.

Next, it was time to make booking feel just as smooth as browsing—by reworking the entire booking flow.

Step 4 — Designing a Frictionless Direct Booking Flow With a Fully Branded Hostaway Checkout

Once guests found the right property—whether through the dynamic listings or the lake-specific pages—the next crucial step was ensuring that booking felt seamless, trustworthy, and consistent. Because even the most beautiful website will lose conversions if the checkout experience feels disconnected or confusing.

Hayward Rentals’ original booking flow relied entirely on the default Hostaway booking engine, which is reliable… but visually plain and not built for luxury hospitality brands. The sudden shift in design breaks trust, especially in higher-end markets where guests expect a polished and cohesive experience.

So in this stage of the project, the goal was not to replace Hostaway’s checkout—but to elevate it.

Booking Is Still Powered by Hostaway (But Now It Looks and Feels Premium)

The final booking step still happens inside Hostaway, because that’s where:

• payments are processed

• availability is managed

• reservations sync with the PMS

But instead of sending guests to a generic Hostaway link, we:

✔ Moved the checkout to a branded subdomain:

book.haywardrentals.com

This immediately increases trust and keeps guests within the Hayward Rentals ecosystem.

✔ Restyled the booking engine to match the Wildwood branding

We customized everything Hostaway allows:

• colors

• button styles

• spacing

• typography (as much as the system permits)

• overall layout cohesion

The result is a booking experience that feels like a natural extension of the main website, not a third-party redirect.

✔ Added clear, intuitive CTAs on every property page

Instead of “Book Now” buttons hidden in odd places, each property page has a prominent, consistent CTA: Check Availability & Book.

This sets the right expectation before guests transition into the Hostaway environment.

✔ Reduced guest friction (and drop-off points)

The new flow is straightforward:

Browse → Explore → Choose → Book

No guessing.
No confusion.
No jarring design shifts.

And because everything is branded, guests are far more likely to trust the process and complete their booking—especially important in a premium vacation region where aesthetics and professional presentation matter.

This step is what makes the entire system feel polished.
The API-powered listings attract the right guests…
the lake pages direct them to the ideal property…
…and the branded checkout gives them the confidence to actually book.

Now the only thing left was ensuring long-term growth—by building out strategic content and SEO pages.

Ready for Step 5?

Step 5 — Adding Local SEO Content & Guides to Support Long-Term Growth

A direct booking website isn’t just about displaying properties—it’s about building visibility, authority, and organic traffic over time.
And one of the most effective ways to do that in the vacation rental industry is through local, search-driven content.

Guests don’t only search for cabins.

They search for:

• events in Hayward WI

• things to do near Round Lake

• Hayward WI fishing tournaments

• best lakes in Hayward Wisconsin

• fall colors in northern Wisconsin

• snowmobiling trails Hayward WI

These search terms don’t lead to OTAs.
They lead to blog posts, guides, and local resources — which is exactly what we added to Hayward Rentals’ site.

Why This Matters for Vacation Rental SEO

Local guides do three powerful things:

1. They attract travelers early in the decision-making process.

Someone searching for “Hayward WI fall events” isn’t ready to book yet—but they will be, and now they’ve already discovered Hayward Rentals.

2. They strengthen the site’s topical authority.

Google trusts websites that demonstrate expertise.

When you publish helpful, location-specific content, Google learns:

“This site is not just a booking platform — it’s a local resource.”

That dramatically improves visibility for competitive keywords like Hayward cabin rentals and Round Lake cabin rentals.

3. They improve internal linking and user flow.

Every guide links back to relevant properties and lake pages.

This keeps guests browsing longer, improving engagement and conversions.

Types of Pages We Added…

To support long-term organic growth, we built out a strategic content foundation:

• Event Pages: Seasonal and annual events that draw travelers to the area, from fishing tournaments to festivals. These attract guests before they start searching for cabins.

• Activity & Things-To-Do Pages: Hiking, boating, snowmobiling, fishing, local restaurants, trail systems—all written for SEO and internal linking opportunities.

• Seasonal Pages: Fall color tours, summer lake trips, winter sports… each season has its own search behavior.

These pages aren’t just filler. They’re a long-term SEO strategy designed to:

• increase organic traffic

• improve rankings for competitive rental keywords

• build trust with guests

• position Hayward Rentals as a local authority

• support direct bookings year-round

And because the website already looks high-end, functions flawlessly, and provides a smooth booking flow, every additional visitor has a higher chance of becoming an actual guest.

Interested in Vacation rental SEO? Read more…

• Keywords for Vacation Rentals: How to Find and Use Them to Boost Airbnb SEO

Conclusion: A Fully Modern, Automated, High-End Direct Booking Ecosystem

By combining a premium Squarespace design with a custom Cloudflare Worker integration, this project transformed Hayward Rentals from a basic Hostaway booking engine into a fully branded, dynamic, SEO-driven direct booking website.

Every key goal…

✔ high-end visual branding
✔ automated property listings
✔ lake-specific SEO pages
✔ a frictionless booking flow
✔ and long-term content strategy—

…was built with scalability, performance, and trust in mind.

The new website finally matches the quality of Hayward Rentals’ 40+ lakeside properties and positions the brand for long-term growth. More importantly, it gives Dustin something the original Hostaway setup never could: a direct booking platform that works as beautifully as it looks.

This is what modern vacation rental brands need—not just a website, but an ecosystem that supports visibility, automation, and conversion.

DIrect Booking Site for HaywardRentals.com, built with Squarespace + Hostaway API integration

Ready to Build a High-End Direct Booking Website for Your Vacation Rentals?

If you're a vacation rental owner or property manager using Hostaway, OwnerRez, Lodgify, or another PMS—and you want a website that is:

• beautifully branded

• professionally designed

• API-powered and automated

• SEO-optimized

• easy to update

• built for more direct bookings

…I’d love to help you.

Whether you need a full custom build or want to start from one of my premium Squarespace templates, I can create a direct booking website that elevates your brand and reduces your OTA dependence—without adding complexity to your workflow.

👉 Explore my templates at martalebre.com
👉 Or contact me directly to request a quote

Your website can be your most profitable asset.

Let’s build something extraordinary.

Frequently Asked Questions

• Can Squarespace integrate directly with the Hostaway API?

  Not natively. Squarespace doesn’t support secure server-side API calls, which means you can’t safely connect to the Hostaway API from the frontend. This is why I built a custom Cloudflare Worker, which securely stores API keys and serves as an encrypted bridge between Squarespace and Hostaway. With this setup, Squarespace can behave like a fully API-powered platform.

• Will my listings update automatically after the integration?

  Yes. Once the Cloudflare Worker is connected, the website pulls live data from Hostaway—including descriptions, amenities, photos, lake/area tags, guests/beds, and availability. Any update made inside Hostaway automatically updates on the website, with no manual editing inside Squarespace.

• Do I need to rebuild my website if I’m already on Squarespace?

  Not necessarily. If your current site is well-structured and on Squarespace 7.1, I can integrate the API layer and build dynamic templates without needing a full redesign. Many clients choose to upgrade their design at the same time (like using my Wildwood template), but it’s not requir

• Can I still use Hostaway’s booking engine?

  Absolutely. Booking still happens inside Hostaway for security, payments, and PMS syncing. The difference is that we brand and style the checkout and move it to a custom subdomain (e.g., book.yourwebsite.com) so the booking experience feels seamless and trustworthy.

• Are location-specific landing pages really important for SEO?

  Yes—extremely. Travelers rarely search for general terms like “Hayward cabins.” Instead, they search for location-based keywords tied to specific areas, lakes, neighborhoods, or regions—for example:

  • Round Lake cabin rentals

  • Tiger Cat Lake vacation homes

  • Moose Lake rentals

  • cabins near Hayward WI
    Building location-specific landing pages gives your website dozens of opportunities to rank for high-intent, geographically focused searches. These pages help guests quickly find properties in the exact area they want while signaling strong local relevance to Google.

• Will this work for portfolios with many properties?

  Yes. This setup is ideal for medium and large portfolios (10–100+ properties). The more listings you have, the more you benefit from automation, dynamic templates, and structured SEO.

• Can this integration support amenities pages, filters, or custom icons?

  Yes. If your PMS provides structured amenity fields, I can build dynamic amenity sections, icons, or filter systems. For Hostaway, this often involves mapping the PMS amenity list to custom icons or categories on your website.

• What happens if Hostaway’s API changes?

  Your Cloudflare Worker can be updated at any time. If Hostaway adjusts an endpoint or releases new features, the Worker can be modified without touching your Squarespace site.

• Will my website load slower with API integration?

  No—usually the opposite. The Cloudflare Worker processes data at the edge (globally), and images can be optimized through Cloudflare as well. Most websites become faster because they no longer rely on heavy native PMS embeds.

• Can you integrate other PMS platforms besides Hostaway?

  Yes. The same architecture works with other PMS systems that offer APIs, including OwnerRez, Lodgify, Uplisting, Hostfully, and others. Each requires its own Worker configuration, but the concept is identical.

• Do I need coding knowledge to maintain the site?

  Not at all. Once the system is set up, you only update your data in Hostaway. The website updates itself. You still use Squarespace normally for content and pages.

• How long does a project like this take?

  Typically 3–6 weeks depending on:

  • number of properties

  • website redesign needs

  • custom filters or lake pages

  • amount of SEO content you want to add
    API integration alone takes significantly less time.