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Holiday houses in Viejo San Juan

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Top-rated holiday rentals in Viejo San Juan

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A quaint indoor balcony area is showcased, featuring a round glass table surrounded by woven chairs. A vase of tropical flowers adds a touch of color. In the background, a well-lit bedroom is visible through shuttered doors.
Condo in San Juan
4.9 out of 5 average rating, 483 reviews

Colonial Old San Juan Apartment

Location The apartment is located in Puerto Rico's political and cultural capital, San Juan. It's within walking distance of the best locations Old San Juan has to offer. Great bars and restaurants, hotels, casinos, San Critobal Castle, Paseo La Princesa , plazas and the cruise terminal are only steps away. In its sorroundings there are also farmacies, transportation services, a post office, stores for shopping,beaches and Cathedrals. The apartment is a 10 minutes drive to the Convention Center and 20 minutes to the international airport,. Spaces Typical of Spanish Colonial architecture the apartment spaces include an indoor balcony, perfect for relaxing, and tall ceilings, up to 20 feet high, sporting traditional Ausubo wood beams. Amenities Full kitchen with an industrial stove and oven, microwave, refrigerator, coffee maker and dinnerware. The cozy bedroom has a comfortable queen bed, a/c and drawers for storage. Living room with Flat HDTV, Blue Ray, DVD player, WI-Fi, Satellite dish. Laundry access in the hall.

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Top Guest favourite
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.
Apartment in San Juan
4.97 out of 5 average rating, 217 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.

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Top Guest favourite
A modern kitchen equipped with stainless steel appliances is complemented by a large wooden dining table. Two sets of brown French doors open to a charming balcony. The interior features high ceilings with exposed beams and polished marble floors.
Apartment in Old San Juan
4.96 out of 5 average rating, 256 reviews

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.

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Top Guest favourite
Apartment in San Juan
4.81 out of 5 average rating, 208 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.

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Guest favourite
Apartment in San Juan
4.92 out of 5 average rating, 273 reviews

In the 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.

ValueFamilyKitchen

Guest favourite
An inviting living area features a spacious white sofa, accent tables, and decorative mirrors on the golden wall. An open kitchen is visible in the background, showcasing modern appliances and a dining table with upholstered chairs, enhancing the stylish design and ambiance.
Condo in San Juan
4.92 out of 5 average rating, 152 reviews

Luxury Romantic Getaway w/Patio & Backup Power

Nestled in the 500-year-old historic Spanish colonial city of Old San Juan, Casa Arcos Blancos offers a unique opportunity to live like a local while enjoying all the luxuries that make you feel right at home. Its superb central location allows you to explore the entire colonial city without having to grab a ride for anything. Conveniently located on Sol Street, you will be at walking distance from supermarkets, pharmacies, shops, restaurants, & world-renowned bars & night spots. Other details

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Guest favourite
Home in San Juan
4.97 out of 5 average rating, 32 reviews

Design Retreat w/ Stone Outdoor Shower – San Juan

Modern 2BR retreat perfect for two couples or friends. Enjoy island light, polished concrete, and a serene stone outdoor shower set amid tropical greenery. Two queen bedrooms with Smart TVs, cozy living area with AC and a projector for movie nights, plus a private terrace with hammock. Solar power, cistern, and fast Wi-Fi add comfort and peace—your stylish San Juan escape. A rare mix of modern design, tropical light, and thoughtful details — crafted for couples seeking calm and comfort.

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Superhost
The living area features a black sofa adorned with colorful Moroccan cushions, complementing the vibrant tiled flooring. A small dining table for two is set beside the open doors, allowing natural light to fill the space. Traditional wall art adds to the cultural ambiance.
Apartment in San Juan
4.87 out of 5 average rating, 101 reviews

Morocco Loft Old San Juan

Discover our charming Moroccan-style Home in the heart of Old San Juan! This vibrant city is alive with music, celebration, and joy around every corner. Its cobblestone streets, warm people, and rich culture make it an unforgettable destination. Our space features handcrafted tiles, exotic lamps, and colorful décor throughout. Just steps from historic forts, top restaurants, and unique shops. Experience the magic of Morocco right here in Old San Juan Puerto Rico this is prime location!

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Guest favourite
Apartment in San Juan
4.88 out of 5 average rating, 490 reviews

The Balconies, Old San Juan Best location!!

Beautiful second floor apartment in the heart of the Old San Juan. A spacious one bedroom apartment with a mezzanine that works as a open extra bedroom. One bed, two sofa beds. One full kitchen, and one bathroom. From the balcony you can get a breathtaking view of the Atlantic Ocean. Excellent location! Walking distance to el Morro, art places, historical monuments, bars and excellent restaurants. Close to the airport, public transportation and taxis. You won't find a better location!!

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Guest favourite
The living area features a cozy grey sofa adorned with yellow pillows, complemented by a wooden dining table. A vibrant artwork hangs on the wall, while a Smart TV is positioned nearby. Natural light illuminates the space from a front door with decorative wooden details.
Condo in San Juan
4.84 out of 5 average rating, 219 reviews

★Dorado★ History & The City Luxury Condo

Dorado is our apartment located in the heart of Old San Juan. Staying at our stylish and properly decorated all in Golden you will enjoy the old city experience. Our apartment is very convenient when it comes to accommodation since it has a separate bedroom with a queen bed, Smart TV on living room and bedroom, dedicated workspace and a balcony that overlooks the Cathedral. Being in the center makes this place one of the best properties in Old San Juan you can stay in.

ValueFamilyTV

Top Guest favourite
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.
Apartment in San Juan
4.99 out of 5 average rating, 181 reviews

The Viewpoint @ The Cathedral in Old San Juan

Furnished apartment in Spanish-style building at Calle San Jose, Old San Juan. 1 bedroom, 1 bath, remodeled kitchen, beautiful original marble floor, an interior balcony. Located in the 3rd floor, the hallway that leads you to the apartment, has a magnificent view to the interior garden. A spiral staircase, at the balcony, takes you to the terrace, and another few steps takes you to the mirador (in which the rest of the city can be seen and part of the mainland).

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Guest favourite
The modern kitchen and living area feature a spacious open layout illuminated by natural light. Sleek cabinetry complements a central island with seating, while a comfortable sectional sofa and large windows offer sweeping views of the skyline.
Apartment in San Juan
5 out of 5 average rating, 34 reviews

Bayview Loft near Escambron Beach, OSJ + Condado

Modern, open-concept studio with stunning views and abundant natural light. Built in 2010, the building is well-maintained, with a reliable generator for peace of mind. This 1-bathroom space features a fully equipped kitchen, dedicated workspace, and includes a private parking spot. Perfect for both work and vacation, it blends comfort, functionality, and Caribbean charm for a relaxing and convenient stay.

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Popular amenities for Viejo San Juan holiday rentals

When is the best time to visit Viejo San Juan?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$344 AUD$292 AUD$321 AUD$259 AUD$234 AUD$231 AUD$243 AUD$262 AUD$236 AUD$222 AUD$246 AUD$276 AUD
Avg. temp25°C25°C26°C27°C28°C28°C28°C29°C29°C28°C27°C26°C

Quick stats about holiday rentals in Viejo San Juan

  • Total holiday rentals

    Explore 650 holiday rentals in Viejo San Juan

  • Nightly prices starting at

    Viejo San Juan holiday rentals start at $57 AUD per night before taxes and fees

  • Verified guest reviews

    Over 62,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    260 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 120 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wi-Fi availability

    640 of Viejo San Juan holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Viejo San Juan rentals

  • 4.7 Average rating

    Viejo San Juan stays receive an average rating of 4.7 out of 5 from guests

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