Pet-friendly holiday 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, 489 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.

WalkabilityOutdoor spacesBackyard

The exterior of a charming two-story building is displayed, featuring vibrant yellow walls. The entrance showcases a large wooden door with a decorative barred window beside it. Two balconies adorned with wooden railings overlook the street, and a vintage street lamp casts a warm glow on the façade.

4.86 out of 5 average rating, 148 reviews

Villa Old San Juan escape 2 adults. we have water

The apartment is spectacular, in The most famous streets of the In Old San Juan, on Calle Sol, it has a kitchen area, dining room, living room, one bedroom, a walk-in closet, and a bathroom. For 2 guests only, with a single queen-size bed. The address is 255 Sol St. Adults only. No children. We have hot water and a single bathroom. At the beginning of the street, you'll find Castillo San Cristóbal, one of the most beautiful stone castles built by the Spanish. Steps from Castillo San Cristobal

WalkabilityNearbyDecor

The living room is furnished with two accent chairs featuring colorful cushions, complemented by a glass coffee table at the center. A television is visible in the background, while bright leaf-patterned wall art adds a vibrant touch to the space. Natural light streams in through the nearby windows.

4.81 out of 5 average rating, 129 reviews

Spacious Apartment on Calle Cerra Santurce/Miramar

Vive la Cerra, and experience Santurce like a true local Ideally located in Calle Cerra / Urban Art District, our neighborhood is brimming with restaurants and bars, offering you a taste of local life. By staying in our place, you'll not only enjoy the comforts of home but also immerse yourself in the vibrant culture of the area. The spacious apartment awaits, just a 20-minute walk from the stunning beaches of Condado and Escambrón, and a mere 5-minute drive to the historic Old San Juan.

Outdoor spacesWalkabilityCheck-in

4.89 out of 5 average rating, 309 reviews

MiramArt 2 bed 2 bath w/ garage. Fully equipped!

Zona chill para relajarte y explorar SJ. Espacio privado, full equipado ¡sí, hasta garaje! comfy y con vibes de joyita escondida. Cafes y spots locales cerca. Cuida el espacio y a los vecinos. No fiestas, humo ni bullicio. Todo chill después de las 10pm. Chill spot to relax, work, and explore the city. Private, fully equipped, parking included, hidden gem vibes. Cafés and local eats nearby. Please care for the place and neighbors. No parties, smoking, or loud noise. Quiet after 10pm.

WalkabilityAmenitiesGetting around

4.99 out of 5 average rating, 147 reviews

Townhouse in Santurce

Ocean Park Beachfront & Pool | Steps to the Sand

This Beach Front Townhouse is located in Ocean Park. One of Puerto Rico’s sought out locations! It is perfect for group trips as well as families looking for the perfect getaway! The Town House is in a gated community which means you will be guaranteed a safe trip. Private parking will be provided. The unit is a 10 minute drive from the airport as well as Old San Juan. You will have a private rooftop facing the ocean and a shared pool on the ground floor to use at your convenience.

PetsOutdoor spacesAccuracy

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.

4.84 out of 5 average rating, 222 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.

Outdoor spacesWalkabilityValue

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.

Outdoor spacesWalkabilityCheckout

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, 100 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.

WalkabilityOutdoor spacesSleep quality

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 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.

PetsOutdoor spacesWi-Fi

4.98 out of 5 average rating, 146 reviews

A dining area is presented with a large wooden table surrounded by six chairs. Natural light fills the space through large windows, which are dressed with sheer curtains. Green plants add a touch of vibrancy, and a pendant light hangs overhead, softly illuminating the setting.

Home in Carolina

Rustic Modern Home |Walk 2 Beach| Close 2 Airport

Guests keep telling me the photos don't do it justice. A 4BR/2BA that actually breathes — room to spread out, plus common space where everyone lands at night. Big beds, AC throughout, 5 minutes from the airport, short walk to the beach. Calm, safe neighborhood, Old San Juan 10 minutes away. Whole-house generator and an 1,100-gallon water tank , so when the island's power goes, yours stays on. Message me and I'll send my restaurant list before you land.

Outdoor spacesWalkabilityCondition

4.97 out of 5 average rating, 109 reviews

2BR La Placita + Parking + Water Tank | Sleeps 6

Stay on Calle Dos Hermanos, just steps from La Placita, a farmers market by day, a nightlife hub by night. Walk to Condado and the beach, or drive 10 minutes to Old San Juan and Ocean Park. This remodeled 1920s casona sleeps up to 6 guests with a queen bed and a full-size bunk bed. Enjoy A/C in all rooms, Wi-Fi, Smart TV, full kitchen, toiletries, and free gated parking. Perfect for families, friends, or anyone wanting the full San Juan experience.

WalkabilityPetsBathroom

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.

WalkabilityCheck-inDecor

Popular amenities for Viejo San Juan pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A cozy living area features a mix of seating, including a white sofa and a light brown chair. A dark coffee table sits centrally, while decorative cushions add a pop of color. A patterned tiled floor complements the walls adorned with artwork, enhancing the home’s character.

4.82 out of 5 average rating, 333 reviews

Coastal-Hip Family Friendly Home

Outdoor spacesWalkabilityLaundry

A private outdoor area features a turquoise pool surrounded by smooth stone flooring. Comfortable seating with tropical-patterned cushions is positioned nearby, alongside potted plants. Natural light filters in, enhancing the tranquility of the space.

4.9 out of 5 average rating, 288 reviews

Steps to Beach, 3BR/3BA, Own Pool, Parking, Gen

Outdoor spacesWalkabilityCondition

The entryway features a natural stone floor leading to a staircase, with a cozy seating area visible on the left. Light streams in from multiple sources, creating a welcoming ambiance. A decorative mirror hangs on the wall, enhancing the aesthetic of the space.

4.81 out of 5 average rating, 181 reviews

Casa Ocean PR

PetsWalkabilityAir conditioning

The exterior of a modern house is presented, featuring a blend of textured walls and sleek surfaces. A decorative panel and a covered entryway enhance the facade. Lush green plants are positioned in the front, and clear blue skies provide a vibrant backdrop.

4.93 out of 5 average rating, 129 reviews

Relax Modern Comfort, Near Dining & Malls…

Outdoor spacesWalkabilityAmenities

A modern, two-story building is framed by lush greenery and sand-colored pathways. Each unit features sliding glass doors that open to private balconies, with minimalist furniture visible. A distinct terracotta seating area adds a warm touch to the landscape, surrounded by a variety of plants.

4.95 out of 5 average rating, 152 reviews

Design Villa w Garden & Jacuzzi | CASA FRIDA by DW

WalkabilityPetsComfort

A private terrace is seen with comfortable seating arranged around a central table. Soft lighting illuminates the area, creating a relaxing ambiance. A hammock is suspended for leisure, and a cooler is positioned nearby, enhancing the outdoor experience.

4.95 out of 5 average rating, 117 reviews

Cozy Great Downtown Oasis

WalkabilityOutdoor spacesNearby

4.96 out of 5 average rating, 106 reviews

Casa Rosada in San Juan, Puerto Rico

WalkabilityOutdoor spacesCondition

The private balcony is adorned with colorful canopies providing shade. A hammock is suspended for relaxation, complemented by seating options and potted plants. Vibrant rugs add texture to the space, offering a serene atmosphere with views of the surrounding greenery and clear sky.

4.9 out of 5 average rating, 163 reviews

Water & Power backup, AC, parking, private terrace

WalkabilityOutdoor spacesSolo travel

Pet-friendly home rentals with a pool

A spacious bedroom features a comfortable bed adorned with soft pillows and an artistic mural reflecting tropical themes. Natural light floods the room through glass doors, which offer a view of the ocean. A cozy seating area complements the vibrant decor.

4.93 out of 5 average rating, 142 reviews

Rare Beachfront Getaway w Pool, Gym, + Balcony!

WalkabilityOutdoor spacesCleanliness

The open living-dining area features a spacious sofa and a dining table surrounded by four chairs. Large glass doors provide access to the balcony, where high-top chairs and a small table overlook the ocean. Modern pendant lights hang above the dining table.

4.89 out of 5 average rating, 160 reviews

Palms & Ocean View 1br 1bth + Pool + Beach Access

WalkabilityOutdoor spacesFamily

A panoramic view of the ocean is captured from a height, showcasing the rolling waves and sandy beach below. The coastline is lined with palm trees, and the clear blue sky complements the shimmering water.

4.82 out of 5 average rating, 130 reviews

Ocean & City View Studio in Condado, San Juan

WalkabilityGetting aroundHospitality

Casa particular in Santurce

Blue lagoon

PetsOutdoor spacesLayout

4.93 out of 5 average rating, 112 reviews

A heated swimming pool is showcased in the foreground, reflecting clear blue skies. Surrounding greenery enhances the scene, with a white structure visible nearby featuring multiple windows. A gazebo is situated to the right, complementing the outdoor space.

4.85 out of 5 average rating, 144 reviews

Urban Paradise

WalkabilityOutdoor spacesBathroom

A panoramic view showcases the vibrant skyline of Condado, with modern buildings lined along the streets. The Atlantic Ocean glistens in the background under a partly cloudy sky, while the lush greenery of local areas adds a touch of nature to the urban landscape.

4.98 out of 5 average rating, 123 reviews

Vista Boriken: 24 Hr. Doorman, Pool, Laundry, Gym

WalkabilityDecorFamily

A rooftop pool area is featured with a small turquoise pool and an open terrace overlooking the ocean. Comfortable seating options are present, including lounge chairs and a shaded area with a cushioned sofa. Lush greenery and distant palm trees enhance the tranquil setting.

4.85 out of 5 average rating, 259 reviews

Spectacular! Roof Pool, 10 steps Beach, WaterTanks

WalkabilityOutdoor spacesNearby

4.94 out of 5 average rating, 194 reviews

A spacious bed with a white quilted cover is positioned near large sliding glass doors, offering unobstructed views of the beach and ocean. Light curtains frame the doors, complementing the serene indoor atmosphere. Soft linens and a decorative pillow add comfort to the setting.

Condo in Carolina

💕Ocean Front Isla Verde Beach Remodeled Pool Pkg

WalkabilitySleep qualityDecor

Private, pet-friendly home rentals

4.95 out of 5 average rating, 151 reviews

The living area features a large white leather sofa paired with a unique side table made of natural wood. An elegant lamp provides soft lighting, while expansive windows showcase panoramic views of the surrounding landscape, including the evening sky transitioning to twilight.

Loft in San Juan

Sunrise Loft: King Bed, Washer-Dryer & Ocean Views

WalkabilityCheckoutParking

4.84 out of 5 average rating, 245 reviews

Condado BEACH Next2Hotels/Bars/Restaurants/Parking

Outdoor spacesWalkabilityLong stay

A view through an arched doorway showcases a modern kitchen with white cabinetry and stainless-steel appliances. A ceiling fan circulates air above the dining area, which includes a table and chairs. A colorful area rug adds warmth, complemented by potted plants.

4.91 out of 5 average rating, 109 reviews

Don Charlie Building Apartment 2

Outdoor spacesWalkabilityAccess

A serene beach scene captures gentle waves lapping against a stretch of golden sand under a vibrant blue sky. White clouds float overhead, and the horizon showcases a tranquil ocean. The shoreline is partially shaded, providing a peaceful atmosphere.

4.98 out of 5 average rating, 111 reviews

Chucho's Place PR

WalkabilityLaundryCondition

5.0 out of 5 average rating, 35 reviews

Romantic San Juan Nightlife / Balcony & King Suite

WalkabilityKitchenSleep quality

4.82 out of 5 average rating, 55 reviews

Boutique Oasis 2BR in Heart of Old San Juan

PetsWalkabilityParking

4.87 out of 5 average rating, 67 reviews

Ocean-View Rooftop 3BR · Old San Juan · El Morro

Outdoor spacesPetsGetting around