Vacation rentals with outdoor seating in Viejo San Juan

Quiet 2BR Loft · King+Queen Beds · Walk Everywhere

Quiet 2BR Loft · Central Location ❤️ Peaceful retreat in the heart of town—tucked away from street noise yet steps to cafés, shops, nightlife & iconic sights (Walk Score 98) ❤️ Historic 200-yr-old loft with soaring ceilings, tile floors & Colonial charm ❤️ King & Queen beds, 1½ baths, full kitchen & open layout, ideal for families & friends ❤️ A/C, fast WiFi, workspace, Smart TV, washer/dryer & secure self check-in ❤️ Guests rave about spotless comfort, location, quiet nights & caring Superhosts

In the Heart of Old San Juan!

Experience the charm of Old San Juan in this colorful apartment, housed in a historic 17th-century building with characteristics that come with its age! To brighten the space, simply open the doors and windows to let the natural light flood in as the shutters do not open. Located just a block from the vibrant nightlife on “Calle San Sebastian” and a short stroll from the “Castillo El Morro”. Enjoy plazas, dining, and shopping all within walking distance in the heart of this famous walled city.

Apartment w/ Private Rooftop | Old SJ | Central AC

Enjoy a stylish experience at this centrally-located PRIVATE apartment with PRIVATE rooftop (no one else has access to unit or rooftop). It is located in the heart of Old San Juan on Sol (Sun) Street, right by most of the nightlife (bars and restaurants). The apartment is close to El Morro, the fort the Spanish Crown used to defend San Juan back in the day. The unit is for six guests, and having more guests is prohibited. Additional guests who stay against the rules pay $50 per night.

Casa Arcos Blancos - Luxury Romantic Getaway

Nestled in the 500-year-old historic Spanish colonial city of Old San Juan, Casa Arcos Blancos offers a unique opportunity to live like a local while enjoying all the luxuries that make you feel right at home. Its superb central location allows you to explore the entire colonial city without having to grab a ride for anything. Conveniently located on Sol Street, you will be at walking distance from supermarkets, pharmacies, shops, restaurants, and world-renowned bars and night spots.

★Rojo★In the Middle of Old San Juan Luxury Condo

Rojo is our apartment located in the heart of Old San Juan. Staying at our stylish and properly decorated all in Red you will enjoy the old city experience. Our apartment is very convenient when it comes to accommodation since it has a separate bedroom with a queen bed, Smart TV on living room and bedroom, dedicated workspace and a balcony. Very quiet and peaceful apartment. Being in the center makes this place one of the best properties in Old San Juan you can stay in.

Old World Charm @the❤ofOSJ

***The price for the 2026 San Sebastian Festival (January 15-18) is for up to 7 guests total, so please do not add more than 4 guests when making the reservation or else the total will go up even more.*** Beautiful location to explore the Colonial & Historical cobblestone streets of OSJ. Just a few steps from some of the oldest structures in PR; El Convento, San Juan Baptiste Cathedral & la Capilla de Cristo. We're also close to other Forts, Museums, Restaurants and more.

San Sebastian and Cruz Apt. 10

This area has very few properties—so few, you could count them on one hand. Right in the middle of the action; the apartment is located in the corner of Calle San Sebastián and Calle de la Cruz. It is conveniently located in the center of everything..... bars and restaurants of La Sanse's strip and OSJ's historic attractions. Good choice for those who want to experience both daily nearby attractions and Sanse's vibrant nightlife. Everything here is just steps away.

The Viewpoint @ The Cathedral in Old San Juan

Furnished apartment in Spanish-style building at Calle San Jose, Old San Juan. 1 bedroom, 1 bath, remodeled kitchen, beautiful original marble floor, an interior balcony. Located in the 3rd floor, the hallway that leads you to the apartment, has a magnificent view to the interior garden. A spiral staircase, at the balcony, takes you to the terrace, and another few steps takes you to the mirador (in which the rest of the city can be seen and part of the mainland).

Best location with pool, steps from beach!

Wake up in a luxurious king bed with premium bedding, gazing out at your private pool framed by lush palm trees. Start the day with breakfast from the fully equipped kitchen, then catch up online with blazing-fast Wi-Fi under the shaded pergola. Cool off in the pool or rinse in the outdoor hot shower before walking just 50 yards to San Juan’s best beach. Ideal for couples, solo travelers, remote workers, or small families seeking comfort and style.

Casita del Sol☀️couples’ HOUSE-rooftop, water views

Casita del Sol offers a rare opportunity to rent an entire house in Old San Juan. Classic Spanish colonial architecture with multiple water views and huge rooftop deck. With an entirely removed secondary suite, it can be spacious enough for two couples or cozy enough for one. On a quiet and peaceful residential block, it is still just a short walk from the liveliest restaurants, bars, and shops and offers the best of life in Old San Juan.

Cozy Terraza on Sol St - Solar powered

Charming remodeled 1 bedroom/1 bath on second floor (no elevator) of a colonial house (over 200 years!) on Sol street, a quiet residential street of OSJ. We live downstairs. High ceilings. Lots of light. Kitchen fully equipped, gas stove, large refrigerator, toaster oven, coffee-maker, microwave, Hi-speed internet (optic fiber). It has a private ¨terraza¨ with a lush garden. Powered by solar panels, plus a water cistern on the roof.

La Bonita Rooftop Studio Apt

Roof top studio suite with kitchen in authentic Spanish colonial architectural building in the center of the old town. The space opens to a terrace on two sides with incredible views. Very private. "Flexible check in" means check in: 10 am to midnight. Overnight check in if night is paid. STREET NOISE. DO NOT RENT THIS APT IF YOU ARE SUSCEPTIBLE FOR NOISE.