Apartment holiday rentals in Viejo San Juan

A comfortable gray sofa is placed against a wall, adorned with a variety of decorative pillows in floral and geometric patterns. A small lamp sits beside the couch on a side table, and an abstract wall art piece is mounted above.

4.97 out of 5 average rating, 219 reviews

Cozy and dreamy Old San Juan.

In the heart of Historic Spanish Colonial City of Old San Juan. This cozy apartment is located at walking distance from restaurants, shopping, cruise port, museums, Convention Center, historical sites and night live. It's a perfect mixture of antique ambient with modern comfort and amenities. The apartament has 1 bedroom, 1 bathroom, totally equiped kitchen, a dining room with setting for 4 people, a living room with a very comfortable full sofa bed and air conditioning all over the apartament.

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, 151 reviews

Penthouse w/ Private Rooftop | Old SJ | Central AC

Enjoy a stylish experience at this centrally-located PRIVATE penthouse 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.

4.96 out of 5 average rating, 214 reviews

Historic 2BR • Walk Everywhere • Quiet 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

4.97 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 Viejo 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.

4.92 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.

4.81 out of 5 average rating, 216 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.

4.95 out of 5 average rating, 188 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, couples, business travelers, or families seeking a getaway. Easy, well‑lit access with no stairs — arrival will be smooth at any hour. Enjoy a spacious living room, fully equipped kitchen, brand‑new bathroom, and a tranquil interior patio/lanai for unwinding after exploring the old city. Book today!

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, 133 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 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.

4.95 out of 5 average rating, 292 reviews

Ocean View Loft Penthouse in Old San Juan

Sol 13 | Rooftop Loft Above Old San Juan Above the rooftops of Old San Juan, the city slows down. Ocean-view loft penthouse with a private rooftop terrace, soaring ceilings, a floor-to-ceiling library, and an exceptionally comfortable king bed. Sunrises, sea breezes, and space rarely found in the historic district. Third-floor walk-up (the final flight is steep), but a short climb to another world.

A cozy seating area is highlighted by a light-colored futon adorned with vibrant cushions. A round table is set with a potted plant, surrounded by wooden chairs. Exposed brick walls add texture, while a floor lamp provides soft lighting in the space.

4.87 out of 5 average rating, 199 reviews

Old San Juan with Parking, 1 Bedr Apt

Our very basic vacation rental in beautiful Old San Juan was built 200 years ago across the street from what used to be the city's gunpowder deposit. It was built 20 feet away from the street for security reasons. Nowadays this space provides a very much needed parking and a green area. We are in the residential part of the Old City and within walking distance to every point of interest.