Holiday rentals in Viejo San Juan

4.82 out of 5 average rating, 217 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.

5.0 out of 5 average rating, 50 reviews

El Morro views, ocean balcony, 3-bed in Old San Juan

Step through a yellow arch onto your private balcony: El Morro rising ahead, the Atlantic wide, the breeze on your skin. The whole apartment is yours. Three bedrooms with AC in each, so nobody shares and everyone sleeps cool. Old San Juan is your front yard: forts, cobblestones, and the best food in the Caribbean, all on foot. Mornings you'll hear the ocean before you see it. Evenings, the sunset behind El Morro is worth every stair. We're Christian and Valerie. Can't wait to have you here.

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

4.91 out of 5 average rating, 473 reviews

An open kitchen area is framed by arches, leading to a charming interior courtyard. Green plants and a small dining set are visible, providing a serene atmosphere. The kitchen features light cabinetry and stainless-steel appliances, contributing to a bright and inviting space.

Home in San Juan

Quaint Colonial Home Old San Juan

Beautiful Spanish colonial home in the north side of Old San Juan where locals live, you are just steps (one block) from the ocean. Unique opportunity to explore the city while staying in an exquisite setting and enjoying the colonial architecture of this space. Discover this UNESCO World Heritage Site through a mix of historic architecture and contemporary culture. Note: This home is registered with the PR Tourism Company and strictly adheres to all established Health and Safety protocols.

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!

4.99 out of 5 average rating, 101 reviews

A serene outdoor space presents a heated pool surrounded by lush greenery. Comfortable seating is located under an umbrella on a wooden deck, while a large planter with tropical plants adds a natural touch. The setting is enhanced by vibrant pink flowers climbing the walls.

Home in San Juan

Old San Juan Gem | Backup Power/Water, Pool + Pkg

Enjoy added peace of mind with solar power, battery backup, a private water cistern, and fiber internet, amenities rarely found in Old San Juan. Stay in a 200-year-old historic home in the heart of Old San Juan, complete with a heated private pool and dedicated parking just steps away. This spacious two-story retreat blends historic architecture, curated Puerto Rican art, and modern comfort, all within walking distance of the city’s best restaurants, shops, and landmarks.

4.97 out of 5 average rating, 30 reviews

#7 Presidential Apartment, City View, Plaza Colon

Experience luxury in this spacious 3-bedroom apartment, boasting spectacular views of Plaza Colón, Fort San Cristóbal, and the Capitol Building. Enjoy the stunning scenery from your balcony, accessible from both the living room and master bedroom. Prime location in the Old City steps from U go supermarket, piers, restaurants, cafe's, on top of a Beautiful souvenir shop. Museums, Forts El Morro, The Cathedral, are all within walking distance. Close to parking garage

4.91 out of 5 average rating, 280 reviews

A vibrant street view reveals charming buildings painted in yellow and other pastel colors, framed by fluffy clouds in a blue sky. The cobblestone road runs through the scene, showcasing parked cars and a glimpse of local life.

Apartment in San Juan

San Sebastian and Cruz Apt. 10

This area has very few properties—so few, you could count them on one hand. Right in the middle of the action; the apartment is located in the corner of Calle San Sebastián and Calle de la Cruz. It is conveniently located in the center of everything..... bars and restaurants of La Sanse's strip and OSJ's historic attractions. Good choice for those who want to experience both daily nearby attractions and Sanse's vibrant nightlife. Everything here is just steps away.

4.95 out of 5 average rating, 239 reviews

A vibrant yellow façade with classic Spanish colonial architecture is highlighted in the morning light. The entrance features an elegant archway, leading into a spacious interior. The street gently slopes down towards the water, surrounded by lush greenery and cobblestones.

Home in San Juan

Casita del Sol☀️couples’ HOUSE-rooftop, water views

Casita del Sol offers a rare opportunity to rent an entire house in Old San Juan. Classic Spanish colonial architecture with multiple water views and huge rooftop deck. With an entirely removed secondary suite, it can be spacious enough for two couples or cozy enough for one. On a quiet and peaceful residential block, it is still just a short walk from the liveliest restaurants, bars, and shops and offers the best of life in Old San Juan.