Holiday rentals with outdoor seating in Viejo San Juan

3BR Penthouse: Walk Everywhere · Patio · King Beds

Big 3BR penthouse in the heart of Old San Juan—walk everywhere while enjoying space, privacy and comfort for your whole group. ♦️ Walk to restaurants, cafés, nightlife & historic sites ♦️ Spacious 2,000-sqft layout ideal for families & groups ♦️ Quiet bedrooms for restful sleep ♦️ 2 King beds + 1 Queen bed ♦️ Private interior patio — rare open-air retreat ♦️ Juliette balconies with vibrant views ♦️ A/C, fast Wi-Fi, full kitchen & laundry ♦️ 2 full bathrooms ♦️ Historic charm with modern comfort

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.

Luxury Romantic Getaway w/Patio & Backup Power

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, & world-renowned bars & night spots. Other details

Beach Cabin|Renovated[3 BR] Walk 2beach+gated prkg

Welcome to our cozy 3-bedroom beach wood cabin in the vibrant Loíza Street area of San Juan. Accommodating up to 7 guests, the cabin features free gated parking, a modern kitchen, new LG washer-dryer combo, A/C in all rooms, a dedicated workspace, and excellent internet. Enjoy the huge L-shaped balcony with hammock and outdoor furniture. Just a 5-minute walk to Ocean Park Beach and close to diverse restaurants, shops, and more. Only 10-15 mins from the airport, 15 mins from Old San Juan.

Jungle Bungalow | 1BR Suite | Private Plunge Pool

Located just blocks from the vibrant Ocean Park Beach, our chic studio bungalow perfectly combines urban convenience with tropical serenity. Step into your private plunge pool or explore Calle Loiza's bustling streets, famous for eclectic dining and unique shopping. Your queen-sized bed features plush comfort with en-suite bathroom, providing a personal retreat. Enjoy the lush garden patio hanging egg-chairs for serene evenings, making every day of your stay memorable and relaxing.

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.

★Dorado★ History & The City Luxury Condo

Dorado is our apartment located in the heart of Old San Juan. Staying at our stylish and properly decorated all in Golden 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 that overlooks the Cathedral. Being in the center makes this place one of the best properties in Old San Juan you can stay in.

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).

Casa Azul | Nightlife & Terrace in Old San Juan

Colorful three-level home in the heart of Old San Juan. Located on Callejón El Tamarindo, this colonial-modern home sits within the historic district, surrounded by restaurants, nightlife, and cultural landmarks. Features a cozy private terrace ideal for sunny days or romantic evenings. The property includes a Tesla-powered backup system, providing comfort and peace of mind during power outages. A vibrant stay in one of Puerto Rico’s most iconic neighborhoods.

Historic Apartment | Old San Juan | Private Patio

Located in the heart of Old San Juan, It sits near the corner of De La Cruz and San Sebastian Street, which hosts most of the nightlife in Old San Juan (bars and restaurants). The apartment is close to El Morro, the fort the Spanish used to defend San Juan back in the day. All bedrooms are equipped with a TV! The unit is for six guests, and having more guests is prohibited. Additional guests that stay against the rules pay $50 per night.

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.