The Boutique Brand That Scaled Big in Puerto Rico: How Capital Jetset Grew 150% in 3 years with Hostaway

Gaps can be problematic or they can be opportunities for growth.

In the early 2010s, Juan Carlos Morales, a seasoned hospitality entrepreneur, spotted a gap in the thriving Puerto Rican tourism sector and saw an opportunity — to merge the high standards offered by boutique hotels with the flexibility of vacation rentals. The result? A unique guest experience that delivered five-star service to guests while maximizing returns on real estate investments.

Today, he professionally manages over 25 high-end short-term rentals located across the territory of Puerto Rico, including the flagship Patio Elba, a boutique hotel in the capital city of San Juan, with the help of Hostaway. With over $15 million in real estate assets under his management, he generates more than $2 million in annual gross rental income.

Capital Jetset At a Glance

• Founded: 2012

• Headquarters: San Juan, Puerto Rico

• Properties: 25+

• 2024 revenue: $2M+

• Assets under management: $15M in real estate

• Employees: 20+

• Partner: Juan Carlos Morales

• Started with Hostaway: 2022

Before Hostaway: A Patchwork of Tools and Growing Pains

Founded in 2012, Juan had grown Capital Jetset’s portfolio to 10 properties by 2022 — roughly adding one new rental a year — when he realized he needed “a real property management system”. He and his team found themselves juggling a patchwork of disconnected tools: Multiple Airbnb accounts, Google Sheets and manual cleaning calendars. There was no centralized dashboard to manage their bookings or performance, and there was a lot of texting — guests, cleaners, vendors, team mates, etc.

The pain points were clear: A lack of automation, poor visibility into performance metrics and too much time and effort wasted on repetitive tasks and other manual work. What Juan was looking for was an all-in-one solution that was scalable, one that would enable them to grow their portfolio from 10 to 30+ properties without having to hire a whole new team.

"With 10 properties, we were wasting time on repetitive tasks and had no centralized dashboard to manage performance."

The Search for a Scalable PMS: How and Why Capital Jetset Chose Hostaway

In their search for the best solution, Capital Jetset evaluated several platforms including Guesty, Hostfully and Lodgify. They compared features and integrations, pricing and ease of use, and particularly, how each tool would work in the context of growing a vacation rental management business in Puerto Rico.

Then they came across Hostaway, on a recommendation from a fellow operator. They found it mentioned in numerous leading industry blogs, read reviews and watched a few webinars before deciding to book a demo. Unlike the previous platforms they had looked at, Hostaway stood out for its strong Airbnb and Vrbo integrations, reliable channel manager, customizable automation tools and excellent customer support. Having made the choice to pick Hostaway, Juan was further impressed by the seamless onboarding process where the Capital Jetset team was carefully guided through migration, set up and customizations to be fully operational in just two weeks.

“Hostaway felt purpose-built for operators like us, managing both urban short-term rentals and boutique hotel-style properties.”

What Makes Capital Jetset Stand Out? 

From its conception, Capital Jetset has carved out a hybrid approach to hospitality in Puerto Rico, offering the personalized touch of boutique hospitality alongside technologically optimized operations and professional real estate management.

Capital Jetset is not just a property manager that operates Airbnbs for owners but a professional property management business holding claim to a significant portfolio of boutique hotels and luxury vacation rentals and an established reputation for providing five-star service to guests — consistently.

How Hostaway Transformed Daily Operations for Capital Jetset

Today, Capital Jetset uses Hostaway as the backbone of their operations.

Hostaway has enabled Capital Jetset to optimize their operations, managing listings across Airbnb, Vrbo, Booking.com and their direct booking website capitaljetset.com, automating guest messaging and enabling a guest response time of less than 5 minutes, coordinating turnover and cleaning, assigning and managing tasks and calendar syncing. They are able to oversee and track performance via custom dashboards and easily provide their owners with reports and financial analysis.

It has also enabled the company to accelerate its growth — scaling from adding just one property per year to five per year, resulting in a 150% portfolio increase in just three years.

Capital Jetset’s favorite Hostaway features

• Time-saving automations for guest communication and check-in

• Unified calendar and reservation system

• Mobile app for on-the-go admin by team members

• Revenue tracking and performance visibility across platforms

• Stripe integration for direct booking payments

Capital Jetset’s top metrics to track with Hostaway

• Revenue per listing

• Occupancy rate by season

• Guest response time (kept under 5 minutes using automation)

• Cleaning turnaround time

• Owner payout consistency

"Hostaway allows us to measure what matters and act fast."

Looking Ahead: With Hostaway, the Best Is Yet to Come

With eyes on the future, Capital Jetset plans to grow its portfolio to over 40 listings by the end of 2025 and acquire more boutique hotel assets across Puerto Rico. The company is also doubling down on direct bookings through its own websites, using Hostaway to reduce OTA dependency and strengthen brand identity.

With Hostaway supporting their operations, their ambitions have grown — having enabled them to pursue new acquisitions, enhance guest experiences and scale faster, without overburdening their team.

"Don’t wait until you're overwhelmed to invest in a PMS. If you're managing more than a few listings, Hostaway will give you the structure and automation you need to scale. You focus on creating great guest experiences and let Hostaway handle the rest."

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