Puerto Rico
Rental Academyby Roberto Green Jr.
The Puerto Rico STR Accelerator · By application

Your first property in Puerto Rico is a decision, not a dream.

A step-by-step program for finding, analyzing, financing, launching and operating short-term rentals on the island. Built on what works in Puerto Rico, not generic mainland advice, so you invest without guessing, overpaying or making costly rookie mistakes.

See If You Qualify
Real estate investor Airbnb Superhost Property manager Puerto Rico market specialist Hundreds of investors educated
60+Video tutorials
15+Tools & templates
WeeklyLive coaching
300+Members
Why most investors struggle

The island rewards the prepared, and quietly punishes everyone else.

Short-term rentals in Puerto Rico can be extraordinary. People rarely lose money because the market is bad. They lose it because they walked in blind.

Agents don't respond

Most people can't get an agent to reply when they find a property they want to see. The good deals are gone before they get a foot in the door. I see houses quickly.

They overpay

Without local comps and a real buy box, off-island buyers routinely pay top dollar and erase the cash flow before they get the keys. I negotiate.

They trust the wrong contractors

Half-finished renovations, blown budgets and disappearing crews. On an island where relationships are everything, the wrong vendor can cost you a season. I vet my contractors.

They can't find financing

Mainland lenders get nervous and local rules confuse them, so they assume they need all cash. The deal dies, or they drain every dollar of liquidity. I have multiple lenders.

They don't understand permits

STR registration, municipal rules and compliance trip up new operators constantly. Get it wrong and a listing can vanish overnight. We get permits expedited.

They underestimate the island

Utilities, logistics, hurricane prep, seasonality and off-island management. The things nobody warns you about until they cost you money. We are connected.

Every one of these mistakes is avoidable. The investors who win aren't smarter or richer. They had the map before they started walking.

Roberto Green, Jr. seated in a navy suit
Your guide · Roberto Green, Jr.

I learned this the expensive way, so you don't have to.

For 7 years I built my career in finance, at State Street Bank and later J.P. Morgan, managing and analyzing large amounts of money.

On paper, it was a great career. But every quarter I'd look at the numbers and realize I was helping build wealth for other people, not creating financial freedom for myself. So I left the corporate world and bet on myself.

I moved into real estate investing and found my passion helping people invest in short-term rentals here in Puerto Rico. I didn't get everything right. I learned the hard way.

"I underestimated renovation costs. I struggled sourcing materials. I showered with gallons of water when the water went out and slept in the heat when the power went out. I heard 'no' from lenders more times than I can count. I almost lost it all."

Those mistakes weren't cheap, but they became my greatest education. Today I'm an Airbnb Superhost. I've helped develop and manage short-term rentals across Puerto Rico's eastern region, and guided investors from all over the U.S. through buying, renovating and operating vacation rentals on the island.

As more people asked me the same questions, I realized I could save others years of trial and error by teaching the system I wish I'd had. That's why I created this program.

This isn't about convincing you I'm perfect. It's about showing you I've already walked the path you're trying to take. You're the one building your future. My role is to be your guide: give you the roadmap, introduce you to the right people, and help you move forward with a strategy tested through real experience.

7 years
Finance at State Street Bank and J.P. Morgan.
2022
Buys an abandoned property in Carolina For Sale by Owner and renovates it into a six-figure income-producing short-term rental.
Today
Airbnb Superhost. Hosts Villa Vista, Villa Verde and Villa Monte, co-hosts Villa Brisa Serena, and develops and manages rentals across eastern Puerto Rico.

Roberto's full story, track record and villas

Let's map your first deal
Inside the work

On the island, not behind a screen.

Properties, guests, investors and the weekly work of running rentals in Puerto Rico.

Why Puerto Rico

One of the most unique short-term rental markets in the United States.

A U.S. jurisdiction with a passport-stamp feel: no currency exchange and no passport for U.S. travelers. In 2024, its visitor economy set a record.

Record tourism demand

Record visitor spending in 2024, and no passport needed for U.S. travelers. A deep, steady demand pool for well-run rentals.

Lifestyle

Beaches, mountains, rainforest and culture. An asset in a place people dream about visiting, and revisiting.

Tax incentives

Incentive programs have drawn investors to the island. Eligibility and conditions apply, and we cover what to ask your CPA.

A maturing hospitality market

Tourism is the island's third-largest private-sector employer. A market that rewards professional operators.

$18BTotal economic impact of tourism in 2024
$11.5BTotal visitor spending, up 14% over 2023
7.5MNon-resident visitors in 2024 (11.7M trips including residents traveling on the island)
1.9MNon-resident visitors who stayed in hotels
$2.1BEconomic output generated by lodging
91,000+Direct tourism jobs, about 9.6% of all employment

Source: 2024 Economic Impact of Tourism in Puerto Rico, Tourism Economics for Discover Puerto Rico. Calendar year 2024.

Important: tax incentives carry specific eligibility rules and obligations, and market conditions change. Inside the program we teach you the right questions to bring to a qualified Puerto Rico CPA and attorney. We don't give individualized tax or legal advice.

The roadmap

8 steps to go from "I want to invest in Puerto Rico" to "I bought my property."

Every step builds on the last. Open any step to see what's inside.

01Step 1

Build your Puerto Rico investment foundation

  • Market fundamentals
  • Regulations
  • Permits
  • Tourism demand
02Step 2

Finding the right property

  • AirDNA
  • PriceLabs
  • Market research
  • Buy box creation
  • Property selection
03Step 3

Funding your deal

  • Conventional financing
  • FHA loans
  • Second-home loans
  • DSCR loans
  • Seller financing
  • Private money
  • Partnerships
04Step 4

Acquisition

  • Due diligence
  • Appraisals
  • Inspections
  • Negotiation
05Step 5

Setup & launch

  • Renovations
  • Design
  • Utilities
  • Furnishing
06Step 6

Operations

  • Airbnb optimization
  • Revenue management
  • Guest communication
  • SOPs
07Step 7

Marketing

  • Direct bookings
  • Social media
  • Influencer marketing
  • Hospitable
08Step 8

Scaling

  • Portfolio growth
  • Team building
  • Automation
Everything you get

Not just a course. A complete operating system for Puerto Rico rentals.

The tools, templates and live support that compress years of trial and error into a clear, repeatable process.

The full Accelerator courseAll 8 steps: find, fund, launch, operate, scale
Weekly live coaching callsBring your deals and get answers in real time
Private community accessInvestors and operators on the island and off
Deal analyzer spreadsheetUnderwrite any Puerto Rico property in minutes
Buy box templatesKnow instantly whether a property fits your criteria
Financing templates & scriptsDSCR, seller finance and private money frameworks
Contractor & vendor documentsScopes, agreements and hiring checklists
Renovation budget templatesPlan and protect your rehab numbers
Airbnb listing templatesTitles, descriptions and photo shot lists that convert
Emergency & hurricane prep plansProtect guests, property and reviews
Vendor & resource directoryVetted Puerto Rico contacts to start with
Also included

Bonuses that close the last "I don't know how" gaps.

Everything you need to purchase a property in Puerto Rico under one proven program.

Bonus 1

My Puerto Rico buy box

The exact criteria I use to filter properties worth analyzing from the ones that waste your time.

Bonus 2

Contractor hiring system

How to vet, scope and manage crews on the island so renovations finish on time and on budget.

Bonus 3

Property analysis walkthroughs

Real Puerto Rico deals underwritten end to end, so you copy the thinking, not just the formula.

Bonus 4

Done-with-you Airbnb setup

We help you build and optimize your listing, pricing and account settings so your property launches ready to book.

Bonus 5

STR launch checklist

The step-by-step list that takes a property from closed to live and booking, with nothing forgotten.

Bonus 6Members only

Hosting & management at 20%

Qualified properties get our team's full-service hosting and management at an exclusive members' rate.

Proof, not promises

Real students. Real properties. Real numbers.

Outcomes from investors Roberto has worked with on the island. Individual results, not typical or promised outcomes.

The property before renovation, with an unused poolBefore
The property after renovation, with a restored poolAfter
Property transformation

6-bedroom, Carolina

Carolina, Puerto Rico
$12,000Average revenue
70–80%Occupancy
The buyers at their lender's officeThe buyers
Villa Verde pool with waterfall at sunsetVilla Verde
First STR deal

Robert Salazar & Kritzie Roberts

Río Grande, Puerto Rico · live in New York
$12,000Monthly revenue
30 daysTo first booking
A single-story home in Puerto RicoProperty
A closing meeting around a conference tableClosing
First-time investor

Luciano Cirino

Trujillo Alto, Puerto Rico · lives in Massachusetts
$335KPurchase price
$25KSaved on price
Victor Rosario, on the right in a cap, with two othersVictor, right
First-time investor

Victor Rosario

Luquillo, Puerto Rico · veteran, moved from Texas
Multi-unitInvestment
VA loanFinancing
Owner earnings screenshot for August 2026Owner's earnings
Five-star guest review screenshotGuest review
Managed remotely

Off-island owner

Owner lives off the island
$130,000+Annual revenue
4.8★Guest rating

Figures reflect specific properties and individual results. They are not typical results or a promise of yours. Your outcome depends on the property, market, financing and your own effort.

In their words.

"We were tired of how expensive real estate was in New York until Roberto showed us new opportunities that generate real cash flow for us."
RKRobert Salazar & Kritzie RobertsSeasoned investors · invested in Río Grande · live in New York
"I spent so much time thinking about buying in Puerto Rico because of fear, but Roberto gave me the confidence I needed to buy my first investment."
ABAndrea BaezPharmaceutical supervisor · invested in Carolina · lives in Maryland
"Just speaking to Roberto saved me months of lost time trying to figure out real estate in Puerto Rico on my own. I have no regrets."
VRVictor RosarioVeteran · invested in Luquillo · moved from Texas
"Roberto went from being a friend to a brother. He helped me accomplish my goal of owning a piece of Puerto Rico for my family."
LCLuciano CirinoBoston police officer · invested in Trujillo Alto · lives in Massachusetts
"If you want to avoid all the mistakes most of us make, hire a mentor like Roberto. If not, keep watching YouTube videos and learn the hard way like everyone else."
PHPaul HerreraSeasoned investor · invested in Carolina · lives in Massachusetts
The room you're joining

The experts who've joined our weekly calls.

Realtors, lenders, property managers, designers, land experts and investors who share exactly how they do it. Members get every live session and the replays.

Eli TorresLocal realtor

Eli Torres

Finding off-market deals across the eastern region.

Veronica MontalvoProperty manager

Veronica Montalvo

Running a rental from off the island: guests, cleaning and maintenance.

Shirley PimentelInterior designer

Shirley Pimentel

Designing spaces that photograph well and command higher rates.

Sebastian DomenechLand expert

Sebastian Domenech

Buying land in Puerto Rico: titles, access, utilities and zoning to check first.

Tony SantiagoLoan officer

Tony Santiago

Financing Puerto Rico deals, including DSCR and second-home loans.

Ben CastroPortfolio investor

Ben Castro

Scaling from one property to a full portfolio on the island.

New guests join throughout the year.

Radical transparency

My own Airbnb & VRBO earnings, out in the open.

I don't just teach this. I do it. Real numbers from properties I operate, so you can see the model working before you join.

$132,755.5212-month revenue
$15,594.79Best month
70%Average occupancy
4.87★Average guest rating · 149 reviews
Airbnb year-in-review earnings screenshot
Airbnb · year in review
Airbnb monthly performance chart
Airbnb · monthly performance
Finished bedroom at Villa MonteAfter

Villa Monte | Trujillo Alto

Full renovation & STR launch
Villa Vista pool at sunset overlooking the coast

Villa Vista | Carolina

Design refresh & furnishing

Guest rating: weighted average of Villa Vista (4.85, 71 reviews), Villa Verde (4.82, 34) and Villa Brisa Serena (4.93, 44) on Airbnb, as of September 30, 2026. Figures reflect specific properties and are shared for transparency. They are not a promise of your results.

Run it yourself

Part of the math that decides everything.

A stripped-down version of the deal analyzer inside the program. Move the sliders. Occupancy is the number people usually get wrong, and it can turn a good-looking deal upside down.

$185
65%
$1,200
$1,800
Estimated monthly cash flow
$0
Gross annual revenue$0
Gross monthly revenue$0
Net annual cash flow$0
Break-even occupancy0%

Simplified on purpose. The real analyzer adds seasonality, cleaning turnover, storm-season vacancy, financing structure and taxes. Illustration only, not a projection.

Run your real numbers with us
Let's be honest

You probably have a few concerns. Good. So did I.

The questions running through your head right now, answered straight.

"Why not just learn from YouTube?"

You can learn pieces for free. The problem isn't access to information. It's sequence, context and the cost of being wrong. YouTube gives you disconnected tactics from markets that aren't Puerto Rico. This gives you one order of operations for this island, plus a person to ask when a real deal is on the line.

"What if I've never owned real estate?"

Then Step 1 is built for you. It assumes zero experience and walks you from fundamentals to your first acquisition. Beginners have no bad habits to unlearn, and follow the system instead of improvising.

"What if I live outside Puerto Rico?"

Many Puerto Rico operators live off the island, and so do many of our students. We teach remote acquisition, vetting vendors from afar and managing without being there. Distance is a logistics problem, and logistics have a playbook.

"What if I don't have a lot of money?"

Before you invest in real estate, invest in understanding every funding option: HELOCs, eligible 401(k) and self-directed IRA funds, selling underperforming assets, private capital, partnerships and creative financing. The skill of funding deals is worth more than the cash itself.

"What if I don't have time?"

The program is self-paced, and the operations side is built on automation, SOPs and systems so it doesn't consume your life. The goal is to buy back your time, not trade more of it.

"What if the market changes?"

Markets always change, which is why you want a framework instead of a hot tip. We teach you to read demand, underwrite conservatively and adjust as conditions shift. Operators who understand the fundamentals adapt.

Two ways in.

Everyone is welcome in the free community. The Accelerator is for people ready to plan a purchase.

The CommunityFree

Learn alongside other future owners.

  • Open to anyone exploring Puerto Rico rentals
  • Get familiar with how buying and hosting on the island works
  • Hosted on Skool
The AcceleratorBy application

Buy your first Puerto Rico property with a guide.

  • The full 8-step course, tools and templates
  • Weekly live coaching calls and the private community
  • All six bonuses, including the members' management rate
The application

Three steps, in order.

Everyone starts in the same place. The readiness check decides whether a strategy call makes sense now or later.

I.

Take the readiness check

Five questions about your experience, capital, timeline and goals.

2 minutes · no payment
II.

See your next step

It appears as soon as you finish: a strategy call with Roberto, or the free community for now.

Instant
III.

Strategy call with Roberto

We talk through your goals and situation, answer your questions, and decide together whether the program fits. Pricing is shared on the call.

30 minutes
See If You Qualify Submitting doesn't book a call or enroll you in a paid program.
Questions, answered

Before you apply.

Anything else, ask inside the free community or on your strategy call.

Do I need to live in Puerto Rico to do this?

No. Many successful operators, and many of our students, run their properties from the mainland. We teach the remote acquisition, vendor-vetting and management systems that make it work.

I've never invested in real estate. Is this too advanced for me?

Not at all. Step 1 assumes zero experience and builds from the ground up. Complete beginners often progress fastest because they follow the system instead of improvising.

How much money do I need to get started?

It varies by deal and financing strategy. We dedicate the strategy call to understanding where you are financially, so we can build a budget or game plan for your next purchase.

How is this different from free YouTube content?

Free content gives scattered tactics from many markets. This gives one sequence built specifically for Puerto Rico, plus tools and live support when a real deal is on the line.

How is this different from working with a real estate agent?

Most agents have little or no investment experience. We actively invest on the island and understand the ins and outs of investing here. We aren't here to show you kitchens and bathrooms. We're here to show you ROI and cap rates.

How long does the program take?

It's self-paced. Many students move through the core material in a few weeks of focused effort, then keep using the tools and coaching as they execute.

Is this only for short-term rentals, or long-term too?

The focus is short-term rentals in Puerto Rico, though much of the acquisition and financing material applies to long-term rentals too. Some clients want an investment; others want to move to the island and don't know how.

What tools will I need?

We reference industry tools like AirDNA, PriceLabs and Hospitable and show you how to use them. Third-party subscriptions are separate and optional where noted.

Do you guarantee I'll make money?

No, and be cautious of anyone who does. We provide education, systems and support. Your results depend on your market, deal, financing and effort. We help you take more calculated risks and feel more confident in your deal.

What about hurricanes and emergencies?

We include emergency and hurricane preparedness planning so you can protect guests, your property and your reviews. It's a core part of operating responsibly on the island.

Can you help me understand Puerto Rico's tax incentives?

We teach the landscape and the right questions to bring to a qualified Puerto Rico CPA and attorney. We don't provide individualized tax or legal advice, but we can point you in the right direction.

How do the weekly coaching calls work?

Live weekly group Zoom calls where you bring your deals and questions and get real-time guidance. Replays are available to members if you can't attend live.

Is there a community?

Yes. A private community of investors and operators, on and off the island, so you're never figuring things out alone.

What if I buy in the wrong area?

Step 2 is built to prevent that, using real data and a defined buy box so you target high-demand areas, not just pretty listings.

I have a demanding full-time job. Can I still do this?

Yes. The program is self-paced, and the operations side is designed around automation and SOPs so it fits around a full-time career.

Do you help with financing or lending directly?

We teach financing strategies and provide templates and scripts. We are an education provider, not a lender, broker or financial advisor. We do connect you with lenders in Puerto Rico who can work with you on pre-approvals.

What happens after I apply?

You take the two-minute readiness check and see your next step right away. If it's a fit, you book a strategy call where we talk through your goals, answer your questions and decide together whether the program is right for you. No pressure.

How current is the material?

The content is maintained, and the live coaching keeps you current as the market, tools and regulations change.

I'm Puerto Rican and want to invest at home. Is this for me?

Absolutely. Local knowledge is an advantage, and this program helps you turn it into a professional, repeatable investing process.

I'm not Puerto Rican but want to invest on the island. Is this for me?

Yes. Despite what you may see or hear online, there will always be opportunities for anyone to invest in a piece of the island. All backgrounds are welcome, and encouraged to give back to our local communities.

Puerto Rico isn't waiting. Neither should you.

You've seen the opportunity and the roadmap. You have a guide who has already made the mistakes, the tools to skip the guesswork, and a community walking the same path. The only thing left is the decision.

Real opportunityA clear pathLive support every weekA community behind you