Holiday 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.

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.

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.

★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.

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.

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.