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, 153 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.

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.

4.99 out of 5 average rating, 100 reviews

Quiet 3BR: Walk Everywhere · 2000 sqft · King Beds

Huge 3BR Spanish Colonial home in the heart of Old San Juan—walk everywhere, enjoy historic charm, and sleep peacefully in quiet bedrooms away from the street. ♦️ Walk to restaurants, cafés, nightlife & historic sites • Walk Score 98 ♦️ Huge 2,000-sqft layout ideal for families & groups ♦️ Quiet bedrooms for restful sleep ♦️ 2 King beds + 1 Queen ♦️ 3 balconies with vibrant street views ♦️ 18-ft ceilings, arches, terracotta floors & original character ♦️ A/C, fast Wi-Fi, full kitchen & laundry

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.

A spacious living room is showcased with a comfortable sofa adorned with orange cushions. An indoor balcony is visible through open doors, allowing natural light to illuminate the area. A large mirror reflects the stylish decor, enhancing the cozy ambiance.

4.92 out of 5 average rating, 279 reviews

Historic 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, 191 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, 134 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 comfortable living area is furnished with a futon and an armchair adorned with bright cushions. Art on the wall adds a touch of color, and natural light filters through wooden shutters, creating a cozy atmosphere in the space.

4.88 out of 5 average rating, 361 reviews

Historic 1BR with Old San Juan at your Doorstep

Our apartment offers easy access to everything Old San Juan has to offer! It's situated a block from the Old San Juan Cathedral and El Convento Hotel, and only a couple of blocks away from the Plaza de Armas, the City Hall, the Fortaleza –Governor’s Mansion- and the famous Calle San Sebastián. It is walking distance to historic sites like the El Morro and the traditional Parque de las Palomas. A short walk will also take you to Paseo La Princesa and the Old San Juan Port.

A covered balcony area showcases wooden chairs and a small table, inviting relaxation. Decorative lanterns hang from the walls, complementing the white façade and dark wooden accents. Large windows offer views into the interior courtyard, providing a connection to the outdoors.

4.94 out of 5 average rating, 263 reviews

Spacious 3 Bedroom Colonial Apt.

RESIDENTIAL BUILDING : QUIET PLACE - 4 ADULTS MAXIMUM-children welcome Beautifully decorated, this 1,200 SF apartment in Calle del Sol, center to services and restaurants. Quietly placed on back of building, 3rd Level. Feels like being at home! . "Flexible check in" means early check in at 10 am, late check out at 2 pm. The building runs its water supply on solar energy, so there will always be water in the apartment!

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.