Meet your guide to Puerto Rico real estate

Want a six-figure short-term rental in Puerto Rico? My name is Roberto Green. I've built them, and I'll show you how.

Former J.P. Morgan and State Street finance professional. Airbnb Superhost. Seven-plus years of investing across wholesale, fix and flips, rentals, restaurants, and development. Today I own, operate, and manage short-term rentals across Puerto Rico's East, and I help investors do the same.

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J.P. Morgan alum State Street alum Airbnb Superhost Boston → Puerto Rico
7+ yrsinvesting in real estate
7strategies executed, from wholesale to STR
4properties owned, partnered & managed
100+five-star guest reviews
300+students in our coaching program
My story

From corporate America desks to Puerto Rico rooftops

I grew up in Boston and started my career in finance at State Street Bank and J.P. Morgan. That's where I learned how money moves, how deals get underwritten, and how institutions think about risk.

Between 2012 and 2016 I did what a lot of people do. I got the apartment, the new car, and had my second child. Then I ended up moving back into my parents' house. I had fallen into the rat race trap, and I knew a paycheck alone was never going to build what I wanted for my family.

Real estate became the way out. I started with wholesale deals, then fix and flips, long-term rentals and Section 8, land, private lending, and even restaurant businesses. Every strategy taught me something the classroom never did.

"The deal is made when you buy. Everything after that is a system."

When I bought Villa Vista, my first short-term rental in Puerto Rico, I had zero STR experience. I found hidden repairs, permit issues, and water and power problems. I waited two years for "the right time" before I bought it, and mentorship is what finally moved me forward. That property taught me my most important lesson: todo tiene que tener un sistema estructurado. Everything needs a structured system.

Those systems are what I use to run my own villas, my partners' properties, and my clients' homes today. They're also what I teach.

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Track record

I've worked every side of the deal

Short-term rentals are my focus, but they sit on top of years of work in other strategies. That's why I can look at a Puerto Rico property and see the full picture.

Primary focus

Short-term rentals in Puerto Rico

I own villas, co-own with partners, and manage homes for clients across Puerto Rico's Eastern region. I handle the purchase analysis, the renovation, the design, the listing, and the day-to-day operations.

  • Airbnb Superhost
  • Own, partner, and client-managed properties
  • Island-specific systems: cisterns, generators, salt-air maintenance, local crews
4properties
4.8★average rating
$8–10K+gross bookings per month
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Short-term rental portfolio

Properties I own, partner on, and/or manage

Real villas, real guests, real numbers. These are the homes behind my Superhost status.

My Villas

Where it started

Villa Vista

Trujillo Alto, Puerto Rico · 6 BR / 2 BA · 10 guests
4.84★Rating
70Reviews
$130K+Annual revenue

Villa Verde

Río Grande, Puerto Rico · 5 BR / 2.5 BA
4.82★Rating
33Reviews
$100K+Annual revenue
Newly launched

Villa Monte

Trujillo Alto, Puerto Rico · 5 BR / 3.5 BA

Newly opened and now taking bookings.

Managed as Superhost

Villa Brisa Serena

Cidra, Puerto Rico · 4 BR / 2.5 BA

I don't own this villa. I manage it for the owner as a Superhost.

4.93★Rating
44Reviews
$80K+Annual revenue
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Before & after

I buy right, then I make it five-star

Most of the value in a Puerto Rico rental is created at purchase and in the renovation. Here's what that looks like.

BeforeAfter
Fix & flip into a short-term rental

Villa Vista

A fix and flip that I turned into a short-term rental. I bought this abandoned property for $180,000 and put $170,000 into fully renovating it, including adding bedrooms. Instead of selling it, I kept it as a short-term rental, and it now produces over six figures a year.

Purchase
170K
Added
Bedrooms
Revenue
$100K+/yr
BeforeAfter
Cosmetic rehab · 50/50 partnership

Villa Verde

The sales price was $370,000, and I negotiated it down to $340,000. The previous owner ran it as a short-term rental and was barely earning $5,000 a month. After a cosmetic rehab, it now averages $10,000+ a month. This is a 50/50 partnership with my client.

Sales price
340K
Previous owner / month
10K+
BeforeAfter
Cosmetic rehab + pool · 80/20 partnership

Villa Monte

The sales price was $370,000, and I negotiated it down to $330,000. I handled all the renovations: cosmetic repairs, an added bedroom, and a new pool. My design team redecorated the entire home. It's an 80/20 split with my client, and I manage it for him.

Sales price
330K
Added
Bedroom + pool
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Student & client results

The people I've worked with

Investors from the mainland and Puerto Ricans on and off the island, in their own words.

★★★★★

Robert Salazar

$21K+ booked in the first 3 weeks live

We closed on his property and finished the cosmetic repairs in 45 days. Three weeks after going live, it had over $21,000 in confirmed bookings.

★★★★★

Luciano Cirino

Saved $30K on the sales price + $15K+ booked in 2 weeks

We negotiated $30,000 off the sales price of his property. Within two weeks of going live, it had over $15,000 in confirmed short-term rental bookings.

★★★★★

Victor Rosario

Bought in Fajardo with a VA loan

Through direct mentorship, Victor saved months of learning and failing on his own. I connected him with the right team of lenders and realtors, and he secured a VA loan. Together we found a property in Fajardo, Puerto Rico, and he bought it with that VA loan.

Andrea Baez

Carolina, Puerto Rico
★★★★★
"Roberto guided me through the entire buying process for my short-term rental. He also connected me with the right lenders to make the purchase happen. Now the property brings in over $10,000 a month, and my family can stay there when they come to visit."
$10K+/month in gross revenue, plus a home base for family visits

Victor Rosario

Fajardo, Puerto Rico
★★★★★
"Roberto saved me months, even years, of trying to research and do everything on my own. He helped me understand that I was eligible for a VA loan, which let me move from Texas to Puerto Rico and buy back the island. I'm very grateful for his teaching and mentorship."
Used a VA loan to move from Texas and buy in Puerto Rico

Luciano Cirino

Trujillo Alto, Puerto Rico
★★★★★
"Roberto was an exceptional mentor. He broke down and managed every step, from finding the property to designing it the way I envisioned with his team. From the pool to the design, he made my dream a reality. Now my family can stay here."
Saved $30K+ on the purchase price, with a fully managed short-term rental while he lives in Boston

Paul Herrera

Condado, Puerto Rico
★★★★★
"Working with Roberto, we were able to increase our monthly revenue. He gave us a lot of tips and design ideas to help us redecorate and rebrand our short-term rental. As a result, our condo in Puerto Rico now gets 30% more bookings and a higher occupancy rate."
30% more bookings and higher occupancy after a redesign and rebrand

Pedro Cardona

Cidra, Puerto Rico
★★★★★
"Working with Roberto has helped us increase our monthly revenue. He gave us a lot of great tips on how to improve our listing. We rebranded, changed the name, and added more strategic beds to raise our occupancy rate. In August 2026 we made over $9,000 in gross revenue. We would recommend Roberto to manage any short-term rental. He's an amazing Superhost."
$9K+ gross revenue in August 2026 after a rebrand and added beds

Olivia & David

Río Grande, Puerto Rico
★★★★★
"Working with Roberto has made this process a lot easier. We were stuck for over two years, searching all over the island and trying to figure out what we could buy. We really didn't understand the numbers. Roberto helped us understand the numbers and gave us a game plan. Now we're excited to be under contract on an amazing property, and he negotiated over $100,000 in savings."
Under contract, with $100K+ negotiated in savings

From my guests

Airbnb Superhost · 100+ five-star reviews · scroll for more →
★★★★★
Everything about Roberto's Villa was beautiful, the scenery, it gave Rainforest vibes, the pool was too nice, our own space, everything you could imagine.
Savannah · Las Vegas, Nevada · June 2026
★★★★★
From the moment we arrived, we felt right at home. The property was exceptionally clean, beautiful, and peaceful, making it the perfect place to relax.
Victor · Rochester, New York · July 2026
★★★★★
This place was amazing, and it was so close to a lot of the activities we all did as a group!! If you're looking for a spot with a lot of privacy, and a very professional host. Come to villa verde!!! Love all the dogs as well
Joel · August 2026
★★★★★
Roberto was a great and responsive host. The home and location was beautiful. Would definitely recommend booking if you're in the area!
La'Elle · Seymour, Connecticut · August 2026
★★★★★
Absolutely beautiful space. Roberto was so kind and responsive whenever we had any questions. The space was exactly as described and in such a peaceful place. Will absolutely be booking again!
Sarai · Los Angeles, California · August 2026
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Why work with me

Why investors trust me with Puerto Rico

I operate what I teach

I'm not teaching theory. I own, partner on, and manage short-term rentals on the island right now, and I deal with the same guests, crews, and permits you will.

A finance lens on every deal

My years at J.P. Morgan and State Street mean I underwrite a property like an institution would. The deal is made when you buy, so we get the numbers right first.

Local knowledge you can't Google

Cisterns, generators, salt air, permits, which towns work and which don't. I've learned Puerto Rico's realities on my own properties so you don't have to learn them the expensive way.

Systems, not guesswork

Villa Vista taught me that everything needs a structured system. You get the same checklists, processes, and vendor playbooks I use in my own portfolio.

Rooted in Puerto Rico

I'm building generational wealth for my family here, and I care about Puerto Rican ownership and community. I'm on the island for the long run.

Bilingual, on and off the island

Whether you're a W-2 professional on the mainland or a Puerto Rican buying back home, I work with you in English or Spanish.

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What I've built

Ways to work with me

The Rental Academy is where I teach. The community, the book and El Castillo are what I'm building alongside it.

MentorshipBy application

Puerto Rico Rental Academy

Home of the Puerto Rico STR Accelerator: a step-by-step program for finding, financing, launching and operating a short-term rental on the island.

See the program CommunityFree

Puerto Rico Short-Term Rentals

The free Skool community for people working toward their first rental in Puerto Rico.

Join on Skool BookBilingual

Seguimos Aquí

A children's book about Puerto Rican identity and the power of owning property.

About the book DevelopmentIn progress

El Castillo

A castle-inspired luxury short-term rental and wedding venue in Trujillo Alto.

About the project
Order the book
English edition Edición en español
Visit the book website: seguimosaquiproject.com
New book

Seguimos Aquí

A bilingual children's book about Puerto Rican identity and the power of owning property.

I wrote Seguimos Aquí for the next generation. For young people growing up in Puerto Rico, and for the diaspora raising kids in the United States. Most of us never heard about real estate or building wealth until we were adults. I want our kids to hear it early.

The book tells a story about staying rooted in our island, knowing where we come from, and understanding that owning land and property is how families build a future that lasts. It's meant to plant a seed. If a child reads it and starts asking questions about homes, land, and money, it did its job.

  • Donating books to local schools so students across Puerto Rico can read it in their classrooms
  • Partnering with nonprofits on the island to bring financial literacy to youth programs
  • Reaching the diaspora so Puerto Rican kids in the States stay connected to the island and its opportunities

In the community

Book donations and collaborations with nonprofits in Puerto Rico
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Let's talk

Ready to invest in Puerto Rico the right way?

Start with the two-minute readiness check. If it's a fit, you book a 30-minute call with me, and we talk about your goals, your budget, and whether a short-term rental in Puerto Rico makes sense for you.

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