Vacation rentals in Viejo San Juan

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.

4.9 out of 5 average rating, 491 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.

ValueFamilyQuiet

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.

ValueFamilyBeach

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.

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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.

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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.

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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

LocationFamilyNearby

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.

4.91 out of 5 average rating, 473 reviews

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.

ValueFamilyComfort

4.95 out of 5 average rating, 197 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!

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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.

4.99 out of 5 average rating, 101 reviews

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.

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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.

4.91 out of 5 average rating, 280 reviews

San Sebastián y 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.

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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.

4.95 out of 5 average rating, 239 reviews

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.

ValueLocationCheck-in

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.

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Popular amenities for Viejo San Juan, San Juan Antiguo vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Viejo San Juan, San Juan Antiguo house rentals

4.94 out of 5 average rating, 110 reviews

Casa Azul | cistern & battery backup Old San Juan

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4.98 out of 5 average rating, 239 reviews

A refreshing pool area is surrounded by natural greenery, with stone accents and a sunlit patio. The pool features clear water and a small seating area, creating an inviting outdoor space. Lush foliage frames the scene, enhancing the serene atmosphere.

Home in Carolina

Villa Estrella PR (near Airport & Beach)

LocationFamilyAir conditioning

4.99 out of 5 average rating, 107 reviews

A modern home exterior is displayed, featuring a clear glass window and a two-car garage door. The entrance is accentuated by a small staircase leading to a covered porch. A manicured lawn and a stone driveway add to the inviting appearance of the residence.

Home in Carolina

Lake View | King Beds | Cistern & Solar | Home Gym

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4.84 out of 5 average rating, 229 reviews

An inviting hallway features two comfortable chairs adorned with green cushions, positioned beside a woven rug and a round wooden coffee table. A stylish mirror reflects a chandelier that hangs above, while greenery from potted plants adds a touch of nature to the space.

Home in Santurce

Classic Miramar House, in the heart of San Juan

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Sturdy wooden double doors are set against a soft blue wall, bordered by elegant wrought iron grilles. Lush greenery from a nearby potted plant adds a touch of nature, complementing the colonial-style architecture. The entrance features stone tiles that enhance the welcoming ambiance.

4.86 out of 5 average rating, 241 reviews

Charming Spanish House in Exclusive Street

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The living area features a brown leather couch complemented by a round coffee table and decorative elements. A ceiling fan and modern light fixtures are present, along with plants that enhance the space. Glass doors open to a private outdoor area, blending indoor and outdoor environments.

4.9 out of 5 average rating, 125 reviews

Water Cistern • Mid-Century Modern House

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4.91 out of 5 average rating, 291 reviews

An open kitchen and living area are visible, featuring modern white cabinetry and a sleek countertop. Two gold bar stools are positioned at the counter, which complements the chic décor. Natural light fills the space through large windows, highlighting the marble flooring.

Home in Santurce

The Garden Miramar 1 • Best Location Ever

LocationFamilyAccuracy

4.88 out of 5 average rating, 125 reviews

The exterior of the house is shown, featuring a modern design with large windows that allow ample natural light. A small balcony above is visible, and a secured entryway leads to the front steps. Lush greenery and a light-colored facade complement the structure.

Home in Santurce

Monteflores House San Juan, Puerto Rico.

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Other great vacation rentals in Viejo San Juan

A compact kitchen area features a modern cooking stove and a decorative backsplash with intricate tile patterns. Glassware is displayed on a shelf above, along with hanging cooking utensils. A framed artwork is positioned on the adjacent wall, adding a touch of color.

4.95 out of 5 average rating, 227 reviews

Welcome to Abby's Apartment! Perfect for couples

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A stylish dining and living area features black and white checkerboard flooring. A contemporary white sofa and a glass table are positioned alongside a woven chair. The kitchen with wooden cabinetry is visible, and a decorative piece hangs on the wall, enhancing the space.

4.84 out of 5 average rating, 783 reviews

Las Virtudes (300gl water tank)

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An outdoor terrace features a covered seating area with a sectional sofa and a dining table surrounded by four wicker chairs. String lights enhance the ambiance, while the view includes surrounding rooftops and clear blue skies.

4.9 out of 5 average rating, 186 reviews

Cozy Colonial Stay • Old San Juan

ValueFamilySleep quality

A spacious living area features a modern sectional sofa and a wooden coffee table. Textured wall art hangs above, while terracotta tiles contribute to the room's warm ambiance. An arched doorway leads to additional spaces, highlighting the building's classic architecture.

4.89 out of 5 average rating, 113 reviews

Cozy Loft in Old San Juan – Prime Location w/ H2O!

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5.0 out of 5 average rating, 37 reviews

Romantic San Juan Nightlife / Balcony & King Suite

LocationFamilyBeach

4.75 out of 5 average rating, 28 reviews

Retro Boutique Loft 5 BR | Heart of Old San Juan

LocationFamilyDecor

4.97 out of 5 average rating, 30 reviews

#7 Presidential Apartment, City View, Plaza Colon

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