Vacation rentals with outdoor seating in Viejo San Juan

The bedroom features a spacious bed with soft linens, complemented by a cozy armchair and a decorative area rug. Large arched windows frame the view, allowing natural light to illuminate the space while highlighting the rich wood ceiling and furnishings.

4.97 out of 5 average rating, 152 reviews

Large Quiet LOFT~ King Bed & in the Center of Town

♥️ Spacious & elegant 2BR LOFT in central Old San Juan ♥️ Steps from dining, shopping, nightlife, & parking ♥️ King & queen beds for ultimate comfort ♥️ Quiet location, tucked away from street noise ♥️ Historic 200-year-old gem with Old World charm ♥️ Air-conditioning, ceiling fans and High-Speed WiFi ♥️ Fully equipped kitchen ♥️ 1½ bathrooms with essentials ♥️ On-site washer & dryer ♥️ Located above our yoga patio ♥️ Walk Score 98~ explore it all on foot! ♥️ Book your vacation with us today ♥️

4.95 out of 5 average rating, 193 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.

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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. (concierge services also available - details below*)

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, 229 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.

A bright bedroom features a spacious bed with a light quilt and neatly arranged towels in pastel colors. The room opens to a private terrace through double doors, showcasing outdoor seating and greenery. A piece of artwork adds a touch of personality to the space.

4.87 out of 5 average rating, 249 reviews

Cozy Terraza on Sol St - Solar powered

A charming one bedroom & one bathroom apartment is located on the second floor of our colonial house on Sol Street, a quiet residential area in Old San Juan. Located in a quiet residential area, above our colonial house. It's a bright and stylish apartment with high ceilings, a fully equipped kitchen with a gas stove, coffee-maker, microwave, toaster oven and large refrigerator, hi-speed wifi, and private ¨terraza¨ with a lush garden. Powered by solar panels, plus a water cistern on the roof.

A spacious terrace is showcased, featuring a sectional sofa with colorful cushions and a coffee table. A large umbrella provides shade, with a view of the sky and ocean in the background. The patterned terracotta floor complements the outdoor seating area.

4.94 out of 5 average rating, 233 reviews

Old San Juan PH with Ocean View Private Terrace

**Ocean View Terrace PH in Old San Juan** Welcome to your dream getaway in the heart of Old San Juan! This luminous penthouse offers the best views of the historic city, where you can soak in the breathtaking sunrises and sunsets from your own spacious, private ocean view terrace. This charming one-bedroom penthouse is designed for comfort and relaxation in the heart of Old San Juan. Come enjoy the rich history, colorful architecture, and vibrant culture that this iconic city has to offer.

The living area features a light-colored sectional sofa adorned with various decorative pillows. Large, open doors invite natural light, revealing a glimpse of the balcony and indoor greenery. A round glass table sits atop a textured area rug, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 277 reviews

Live Like a Rum Baron in a 200 Year Old Mansion!

Have you ever wondered what it would be like to live in a palace? Ours is a romantic 200-year-old architectural wonder built for one of San Juan's earliest rum barons and remains one of the most beautiful properties in The old city. It features soaring, 18-foot ceilings, cathedral-style acoustics, marble floors and Moroccan tiles. You'll be surrounded by simple beauty, shower in a gigantic Roman spa, cook in an inspirational kitchen and drink your morning coffee on your private balcony.

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.

4.92 out of 5 average rating, 137 reviews

Casa Arcos Blancos - Luxury Romantic Getaway

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, and world-renowned bars and night spots.

The living area features a comfortable sofa with red accent pillows, complemented by a wall-mounted TV. Natural light filters through two wooden shuttered windows, adding to the relaxed ambiance. A large green plant is positioned near the entrance, enhancing the welcoming decor.

4.9 out of 5 average rating, 174 reviews

★Rojo★In the Middle of Old San Juan Luxury Condo

Rojo is our apartment located in the heart of Old San Juan. Staying at our stylish and properly decorated all in Red 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. Very quiet and peaceful apartment. Being in the center makes this place one of the best properties in Old San Juan you can stay in.

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.

4.92 out of 5 average rating, 236 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.

Top guest favorite

A spacious living area is highlighted by a cozy sectional sofa, accompanied by a coffee table featuring a clear vase filled with white foliage. Full-length windows provide a breathtaking view of the Atlantic Ocean, allowing natural light to fill the space.

4.99 out of 5 average rating, 101 reviews

Superb Beachfront. Epic view!

Epic unobstructed view of the Atlantic Ocean, high-level. Luxury spacious 1350 SQFT, richly custom design, furnished, fully outfitted, and stunning kitchen with superb "Dekton" quartz countertops & dining table, makes meals a melody! Chloride-free water system! Open-plan space, full-length windows provide the interior natural sunlight, extraordinary views, and illumination, complemented by amazing cross ventilation. Bedrooms provide queen-size beds.

Top guest favorite

A tranquil private pool reflects the clear blue sky, surrounded by lush greenery and palm leaves. The modern apartment's large glass windows allow for abundant natural light, while a shaded outdoor seating area and hammock can be seen beside the pool.

4.99 out of 5 average rating, 251 reviews

Best location with pool, steps from beach!

Wake up in a luxurious king bed with premium bedding, gazing out at your private pool framed by lush palm trees. Start the day with breakfast from the fully equipped kitchen, then catch up online with blazing-fast Wi-Fi under the shaded pergola. Cool off in the pool or rinse in the outdoor hot shower before walking just 50 yards to San Juan’s best beach. Ideal for couples, solo travelers, remote workers, or small families seeking comfort and style.