Apartment holiday rentals in Viejo San Juan

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, 279 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.

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, 156 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.

Apartment in Viejo San Juan

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.

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.

4.97 out of 5 average rating, 260 reviews

4.82 out of 5 average rating, 218 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.

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, 136 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 shops. Enjoy the beach being just steps Playa del Capitolio or a longer scenic walk to the Escambron beach and recreation area. The loft is a quiet, tranquil loft insulated from the heat and busy streets when you need a break to recharge on your trip.

4.96 out of 5 average rating, 217 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. ♦️ Just steps to restaurants, cafés, nightlife & historic sites • Walk Score 98 ♦️ Quiet King bedroom + Queen bedroom with balcony views ♦️ Soaring 18-ft ceilings, arches & authentic character ♦️ A/C & ceiling fans in every room, fast Wi-Fi, Smart TV ♦️ Great for families, couples & small groups who want to walk everywhere

4.95 out of 5 average rating, 198 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 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.

4.77 out of 5 average rating, 122 reviews

Peace of mind

We’ll make planning your visit easy! La Tranquilidad is in Down Town Old San Juan, close to public transport and San Juan International Airport. It’s a Small corner, first floor apartment, that is walking distance to: historic monuments, parks, restaurants and bars. In summary, right in the heart of art and culture. Please be aware that you may experience music and noise during night hours, specially on weekends.

4.95 out of 5 average rating, 296 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.

4.86 out of 5 average rating, 416 reviews

Hidden Gem in Old San Juan

This is a cozy one bedroom, one bathroom apartment with a queen size bed, toiletries included and fresh clean bath towels and beach towels. It has a fully equipped kitchen with everything you need from pots & pans to oils & spices. A living / dining room area with a sofa and dining table that sits 4. A small cozy terrace with a bistro table & chairs under a nice trellis garden.

Popular amenities for Viejo San Juan apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A colorful street scene features buildings with vibrant exteriors in shades of purple, blue, and pink. Balconies with decorative railings add charm, while cobblestone pathways invite exploration. A resident walks along the street, contributing to the lively neighborhood atmosphere.

4.91 out of 5 average rating, 258 reviews

First Level Charming Calle Cruz Apt

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, 149 reviews

Lively Chic Old San Juan Balcony Suite

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

4.94 out of 5 average rating, 188 reviews

Casa Antonio OSJ.

A charming street in Viejo San Juan is lined with colorful buildings, showcasing architectural details such as wrought iron balconies and decorative façades. The cobblestone pavement adds character, while a single pedestrian is seen walking past parked cars under clear skies.

4.9 out of 5 average rating, 102 reviews

Patios de La Cruz

Apartment in Viejo San Juan

The image features a view from a balcony overlooking Cristo Street at night. Cobblestone streets and parked cars are visible, with soft street lighting illuminating the historic buildings. Decorative plants and illuminated pallet furniture enhance the balcony ambiance.

Old World Charm @the❤ofOSJ

4.93 out of 5 average rating, 332 reviews

Superhost

A cozy studio space is presented with a queen-sized bed, flanked by two dark sofas. A kitchenette is visible in the background, featuring wooden cabinetry and essential appliances. Natural light enters through a window, complemented by light curtains and a decorative wall piece.

4.83 out of 5 average rating, 486 reviews

Posada Amparo - Apartment # 2

The family room features a large, cozy layout with a contrast of blue upholstery and a checkered tile floor. Artwork adorns the walls, while a ceiling fan offers comfort. Natural light enters through the open doorway, leading to a small balcony.

4.81 out of 5 average rating, 183 reviews

Historic Apartment | Old San Juan | Private Patio

Private apartment rentals

The exterior features a vibrant blue facade with contrasting black wrought iron railings and doors, framed by yellow and pink buildings. The interior showcases a kitchen area defined by dark wooden cabinetry and an archway leading to a grand staircase, accented by exposed beams.

4.96 out of 5 average rating, 54 reviews

Old San Juan Gem, Prime Spot: Patria Historic Loft

4.8 out of 5 average rating, 25 reviews

Casa Blanca | Old San Juan · Walk Everywhere

A historic building exterior is showcased, adorned with large balconies and intricate wrought iron railings. The façade features a vibrant green color with contrasting white details. The main entrance includes multiple doors with decorative features, highlighting the architectural charm of the area.

5.0 out of 5 average rating, 80 reviews

Amor SanSe

A bright bedroom is featured with a queen size bed adorned with a leaf-patterned comforter. A smart TV is mounted on the wall, while a cozy hammock and a chair made from tropical fabric add to the space. Natural light enters through a window, enhancing the room's relaxed ambiance.

4.85 out of 5 average rating, 48 reviews

The Tropical Apartment | AC | Old San Juan Oasis

A cozy living area is seen featuring a dark sofa, accented by decorative cushions. A woven area rug complements the space, where natural light filters through a nearby window. A dining table and chairs are positioned in the corner, and a ceiling fan is visible above.

4.91 out of 5 average rating, 98 reviews

Prime location, charming, spacious, no stairs!

The open-concept loft features a modern design with large windows offering views of the Atlantic Ocean. A dark sofa is positioned near a glass coffee table, while a spacious bed is visible in the background. Contemporary light fixtures hang from the ceiling.

4.82 out of 5 average rating, 96 reviews

Atlantis modern living with panoramic ocean views

A spacious living room is illuminated by natural light through large balcony doors. The room features a mix of comfortable seating arrangements including a sofa and armchairs, a ceiling fan, and decorative elements that enhance the open, airy atmosphere.

4.89 out of 5 average rating, 66 reviews

Charming Colonial Stay • Old San Juan

5.0 out of 5 average rating, 18 reviews

Amazing View to Old San Juan City!

Apartment rentals with a hot tub

A private balcony features a wooden table and two matching chairs, overlooking the tranquil lagoon waters. A small plant is placed at the center of the table, with vibrant blue skies and distant city views creating a serene backdrop.

4.8 out of 5 average rating, 110 reviews

Sunrises Near Beaches+Power+Private Balcony

An outdoor hot tub is surrounded by a natural bamboo fence, providing privacy and a serene atmosphere. A wooden stool and a small red step stool are positioned nearby, while lush greenery enhances the relaxing environment.

4.96 out of 5 average rating, 115 reviews

>We have water< Hidden Paradise w/HotTub near A/P

4.97 out of 5 average rating, 116 reviews

A private balcony features comfortable seating arrangements overlooking the serene bay. The spacious outdoor area is adorned with modern furniture and provides an unobstructed view of the water and surrounding greenery.

Apartment in Cataño

Bella Bahía1 Wonderful Sea View! 2Beth 2Bath

A wide view of the waterfront reveals glistening turquoise waters, with rocky outcrops and a distant shoreline lined by modern buildings. The sky appears bright blue, scattered with fluffy white clouds, enhancing the scenic backdrop of the seaside landscape.

4.88 out of 5 average rating, 128 reviews

Amazing Ocean View 13 ;Generator+water, pool

4.89 out of 5 average rating, 200 reviews

Apartment in Santurce

PH/ Water Cistern+Jacuzzi +Private Nook | Sleeps 4

Superhost

4.84 out of 5 average rating, 110 reviews

Centric Paradise Villa | Pool | Cruise ports

4.96 out of 5 average rating, 114 reviews

Apartment in Santurce

Epic Ocean View, 23 floor, Balcony & Free Wi-fi

Superhost

A well-lit bedroom features a spacious bed with a decorative heart-shaped towel design. A tray holds two glasses and a potted orchid, set against a calming backdrop of light colors. A lamp gently illuminates the space, enhancing its serene ambiance.