Vacation rentals with outdoor seating in Viejo San Juan

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.

Spotless Private Retreat: AC, Balcony & Parking

Welcome to our bright and peaceful home! Relax in the hammock, meditate or do yoga on the private balcony. Enjoy the fully equipped kitchen, fast Wi-Fi, TVs and air conditioning throughout the apartment. Driving? No worries - we have a free parking spot. And a short ride, you can easily explore Old San Juan, hit the beach, or head to the airport. Arriving late or leaving early? Our self-check-in process makes it easy and hassle-free. We can't wait for you to experience our cozy retreat!

Garden Oasis, Steps to the Beach

We are located steps from beautiful Ocean Park Beach. This 1 bedroom/1 bath 2nd floor apartment is nestled among tropical flowers, orchids and foliage. It includes an equipped kitchen, linens and a futon in living area - plus a new bathroom and A/C. The garden is gorgeous!!!! Coquis serenade you in the evening plus the fountain and wind chimes are devine. There are boogie boards, a kayak and even paddleball. Amazing restaurants and a variety of bars are just a block away on Calle Loiza.

Blue Balcones 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 equipped, gas stove and large refrigerator. Hi-speed internet (optic fiber). Two private balconies overlooking Sol st. With 17 solar panels and two Tesla batteries no worries about power outages! Water cistern on roof. Walking distance to everywhere in OSJ. You will love it!

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.

#1 Isla Verde Private Apt-breakfast/beach/airport

Power Generator/ cistern. PRIVATE APT. Close to beach and airport! Relax in this boho unit. 5 min driving to the airport, close enough for a quick transfer but located in a dead end, tranquil street; 5 min walking to the beach; 10 min driving to Old San Juan. Enough parking in front of properties. Near recreational park, tennis and basketball court. Full bed, TV, coffee maker, fridge, microwave, single stove top, and Wi-Fi. Beach chairs, towels, umbrella provided. Ground floor.

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.

Cozy apartment with patio

Enjoy this peaceful and centric lodging in an area with lots of cultural and recreational diversity. Located ten minutes from Luis Muñoz Marín International airport, it is walking distance from beaches in Ocean Park and Condado, supermarkets, museums, bars, restaurants and plazas. It is a separate apartment of an antique house in a valuable historical zone. Most importantly is to enjoy your stay with utmost respect for the neighbors. No parties or loud music are allowed.

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.

Santurce Arts District in Urban Oasis Penthouse

An 'urban oasis' in the center of San Juan's Santurce Arts District -see the full listing for details. A note on booking: Since I started hosting AirBnb guests in 2009 I've always met my guests on arrival (no lockboxes) and been on-site during their stay. Since I'll be traveling often this year, I only open dates a couple of weeks in advance when I know I'll be in San Juan. But plans change, so feel free to send a note and see if I can unblock your dates.

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.

Joyfulgarden Studio, few blocks from the beach!

Located in a quiet street with only local traffic, you will be few steps to the local supermarket open 24/7, pharmacy, restaurants, coffee places in Calle Loíza and barely three blocks to Parque Del Indio beach. You’ll be able to enjoy a peaceful stay! Note: some nights the coquis (our national frog 🐸) are loud, some people are not used to it, but once you do is like a singing concert of nature.