Old San Juan
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Start your own vacation rental business in Old San Juan, Puerto Rico
With its cobblestone streets, colorful colonial buildings, and centuries of history overlooking the sea, Old San Juan is Puerto Rico’s most iconic neighborhood—and a prime destination to build a profitable vacation rental business. Travelers from around the world come here for charm, culture, and unforgettable city views. That’s where Casiola comes in—our proven franchise model gives you everything you need to create a thriving, fully managed short-term rental business in this world-famous location. Get your free franchise market analysis for Old San Juan, Puerto Rico.
Interested? Call us today at 1-800-486-6650 or email us at [email protected]
Russ – Director of Franchise
Becoming a Casiola franchisee is a game-changing opportunity
Make more,
save more
Make more money with our award-winning marketing and revenue management, and save on expenses with our technology, automation, and buying power.
Grow your business faster
Add more homes to your inventory quickly with our proven owner-acquisition platform and business development processes.
Create Work/Life balance
Achieve a more fulfilling work and personal life by leveraging our shared services, such as guest relations and accounting.
Be part of the Casiola community
Learn from the best and share your expertise from Old San Juan with our partner community.
Starting a vacation rental company in Old San Juan
Opportunities in the Old San Juan vacation rental market
Old San Juan is a bucket-list destination that delivers nonstop demand from cruise ship passengers, culture lovers, digital nomads, and international tourists alike. With limited space for new development, the area’s historic buildings are often converted into charming boutique apartments and vacation homes—exactly what travelers want when visiting this storied city. Guests are drawn to walkable access to Castillo San Felipe del Morro, lively plazas, museums, and incredible restaurants. But they don’t want just any stay—they want style, space, and local flavor. With Casiola’s full-service franchise model, including expert marketing, smart pricing, and 24/7 guest care, your vacation rental in Old San Juan can stand out in a market where uniqueness is everything.
Business opportunities
Business opportunities in the Old San Juan vacation rental market
The vacation rental market in Old San Juan is packed with high-return opportunities, especially for owners who invest in style, authenticity, and quality service. With the area’s walkability, endless photo ops, and proximity to cruise ports and nightlife, demand stays high all year. Many properties have historic appeal and architectural charm that guests can’t find in modern resorts—making them ideal for short-term rental success. Add in the consistent flow of cultural events, festivals, and government tourism support, and you have a market ready for growth. With Casiola’s full franchise model, you gain access to all the tech, operations, and branding you need to run a scalable, guest-loved vacation rental business in Puerto Rico’s crown jewel.
Why Old San Juan is perfect for a Casiola franchise
Old San Juan is one of the few places where history, culture, and tourism demand combine perfectly for short-term rental success. Travelers expect more than a clean place to sleep—they want a memorable experience in a space that feels as special as the city around it. That’s exactly what you’ll offer as a Casiola franchisee. While we handle cleaning, linens, maintenance, reviews, and guest support, you focus on growing your business in one of Puerto Rico’s most desirable destinations. In a market where guest satisfaction and standout service are everything, Casiola gives you the platform to deliver both—at scale.
Territory highlights
Territory highlights for your future guests
Guests visiting Old San Juan will step into a living postcard of Caribbean history and charm. They’ll walk along 500-year-old fortresses, sip piña coladas in breezy plazas, and browse local artisan shops tucked into vibrant colonial buildings. From La Fortaleza to El Morro, every block is filled with stories, flavors, and rhythm. It’s the perfect destination for culture lovers, romantic getaways, and first-time visitors alike. As a Casiola host, you’ll offer a professionally managed, beautifully maintained vacation home that matches the magic of Old San Juan—while you grow a rental business built on elegance, heritage, and unmatched guest experiences.
