Apartment holiday rentals in Viejo San Juan

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, 152 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.

The bedroom features a spacious bed with soft linens, complemented by a cozy armchair and a decorative area rug. Large arched windows frame the view, allowing natural light to illuminate the space while highlighting the rich wood ceiling and furnishings.

4.96 out of 5 average rating, 213 reviews

Quiet 2BR Loft · Walk Everywhere · King+Queen Beds

Quiet 2BR Loft · Walk Everywhere ❤️ Peaceful retreat in the heart of Old San Juan ❤️ Tucked away from street noise yet steps to cafés, shops, nightlife & iconic sights · Walk Score 98 ❤️ Spacious open loft layout · King & Queen beds, 1½ bathrooms & full kitchen ❤️ Ideal for families, close friends & guests comfortable sharing space ❤️ Historic 200-year-old home with soaring ceilings & Colonial charm ❤️ A/C, fast WiFi, Smart TV, washer/dryer ❤️ Guests love the quiet, comfort & unbeatable location

A light-filled living area features a comfortable beige sofa adorned with colorful accent pillows. A vibrant abstract painting hangs above, complemented by a sleek glass coffee table. Contemporary decor is found nearby, enhancing the modern aesthetic of the space.

4.99 out of 5 average rating, 278 reviews

Dreamy Old San Juan Apartment

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

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.

4.81 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.

4.92 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.

4.95 out of 5 average rating, 190 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.

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, 162 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.

4.95 out of 5 average rating, 293 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 sleeping area is highlighted by a spacious bed covered in a beige quilt. An orange decorative pillow adds a pop of color against the neutral linens. Two framed prints adorn the wall above the bed, while a bedside lamp provides subtle lighting.

4.96 out of 5 average rating, 148 reviews

Lively Chic Old San Juan Balcony Suite

This newly remodeled suite is located in the perfect location to explore Old San Juan. Trendy restaurants, hip bars, coffee shops and mini market are all less than a block away. With city views from the balcony, it features high ceilings, comfortable queen bed, smart TV, air conditioner, emergency water storage tank and a fully equipped kitchen with complimentary Puerto Rican coffee and treats.