Apartment holiday rentals in Viejo San Juan

4.96 out of 5 average rating, 210 reviews

Historic 2BR~Walk Everywhere• Balconies • King Bed

Historic 2BR Spanish Colonial home in the heart of Old San Juan—walk everywhere, enjoy authentic architecture, and take in the city from balconies overlooking the street. ♦️ Walk to restaurants, cafés, nightlife & historic sites • Walk Score 98 ♦️ Quiet King bedroom + Queen bedroom with balcony views ♦️ Soaring 18-ft ceilings, arches, beams & original character ♦️ A/C, fast Wi-Fi, workspace, full kitchen & nearby laundry ♦️ Great for families, couples & small groups who want to walk everywhere

4.95 out of 5 average rating, 181 reviews

Classic Old San Juan •1rst Floor•Best Location•

Best in Old San Juan! Classy and beautifully restored colonial‑style building. Our 2BR apartment blends historic charm with modern comfort. Perfect for cruise ship visitors, vacationers, romantic couples, business travelers, or a family getaway. Easy, well‑lit access, no stairs; arrival will be smooth at any hour. You’ll find a spacious living room, fully equipped kitchen, a brand-new bathroom, and a tranquil interior patio/linai for unwinding after adventuring the old city. Book with us today!

4.97 out of 5 average rating, 259 reviews

Natural light fills the living area through open shutters, illuminating a modern seating arrangement. A stylish wooden coffee table sits at the center, complemented by artistic decor. The balcony overlooks Calle Sol, enhancing the apartment's connection to the vibrant surroundings.

Flat in Old San Juan

Casa Rosabella: Romance and Luxury in Old San Juan

Casa Rosabella is an elegant and modern apartment in Old San Juan. One bedroom,one bathroom,fully equipped with modern decor and old colonial charm. Casa Rosabella has everything you need. Modern kitchen with amenities, Inverter A/Cs , Smart TV to stream and WiFi, Washer, Dryer, Balcony and more. Property is on the 2nd floor because of the high ceilings must be prepared and able to climb up to 30 steps. No parking on the property. ⚠️Only Two Guest/Not infant/children/animal/pet friendly.

4.81 out of 5 average rating, 214 reviews

Cozy Historic Ruin Apartment

Located in the heart of Old San Juan, this unique and special place enables you to experience a fully authentic colonial experience- the most authentic you will get in Old San Juan. This renovated ruin apartment conserves the historical architecture from Old San Juan at a maximum potency, while offering a comfortable and cozy stay. Perfect for any small family, couple or group of friends seeking to enjoy what Old San Juan has to offer, from restaurants to forts, in a fully cultural experience.

4.92 out of 5 average rating, 278 reviews

Charming Colonial Flat, 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.

A private rooftop garden features a spacious seating area with a blue sofa next to a wooden coffee table. The area is adorned with decorative plants and a dining table surrounded by white chairs. Shade is provided by a black canopy overhead.

4.88 out of 5 average rating, 145 reviews

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.

A light-filled living area showcases a gray sectional sofa and a blue accent chair. A wooden coffee table with decorative items is centered in the space. A lush plant adds a touch of greenery, while artwork enhances the wall. The staircase leads to an upper level.

4.94 out of 5 average rating, 130 reviews

Enchanting Spanish Colonial Loft in Old San Juan

Discover the enchantment of Old San Juan in this charming Spanish colonial apartment, perfectly nestled in the historic heart of Puerto Rico’s most iconic city. Walk everywhere, from historic parks and landmarks, restaurants, coffee shops, and shopping. Just steps away from Playa del Capitolio or a longer scenic walk to the Escambron beach and recreation area. The apartment is a tranquil loft insulated from the heat and busy streets when you need a break to recharge on your trip.

A spacious rooftop terrace features a comfortable sectional sofa and two blue chairs, offering a panoramic view of the surrounding rooftops and cityscape. The scene is complemented by a clear blue sky and fluffy clouds, creating a serene outdoor space.

4.99 out of 5 average rating, 183 reviews

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).

4.99 out of 5 average rating, 290 reviews

A tranquil private pool reflects the clear blue sky, surrounded by lush greenery and palm leaves. The modern apartment's large glass windows allow for abundant natural light, while a shaded outdoor seating area and hammock can be seen beside the pool.

Flat in Santurce

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.

The entrance features a vibrant turquoise wall contrasted by white trim. A single black door with decorative grilles is flanked by two narrow planters containing small green plants. A lantern hangs above the door, providing a welcoming illumination.

4.94 out of 5 average rating, 161 reviews

Old San Juan Ocean View With Outstanding Location

Welcome to “Casa Azulia”, Old San Juan, Puerto Rico. Newly restored luxury apartment, PRIME LOCATION, within a short walking distance to: • 3 min walk to Saint Cristobal Fort. • 10 min walk to El Morro Fort. • 2 min away from the most renowned local bars, restaurants and hangouts. • Just steps away from the apartment the most impressive ocean view walk in the whole city. • Around the corner from where the viral “Despacito” music video was filmed.

A scenic waterfront walkway is shown, featuring a wide grassy area bordered by a low stone wall. The ocean extends to the horizon under a clear blue sky, with some clouds scattered overhead. Buildings are visible in the background, adding a colorful urban touch.

4.81 out of 5 average rating, 136 reviews

La Garita Ocean View at Old San Juan

Charming ocean view one-bedroom apartment in the heart of Historical Old San Juan, right next to the iconic 16th-century Castillo San Cristobal. Fully equipped with AC, WIFI, a full-size bed, laptop desk, and a futon in the living room, this cozy apartment is ideal for a comfortable stay. Walking distance to supermarkets, shops, museums, cafes, and restaurants, it offers the perfect mix of history and convenience for your San Juan adventure.

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