Vacation rentals with outdoor seating in Viejo San Juan

4.95 out of 5 average rating, 194 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. (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, 231 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, 251 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.

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, 153 reviews

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

Spacious & quiet 2BR LOFT in central Old San Juan * Steps from local cafes, shops, nightlife & Old San Juan's iconic sights * Walk Score 98~ explore it all on foot! * Quiet location, tucked away from street noise * Historic 200-year-old gem with Old World charm & decor * King & queen beds for ultimate comfort * Air-conditioning, ceiling fans & high-speed WiFi * Fully equipped kitchen * 1½ bathrooms with essentials * On-site washer/dryer * Secure self-check-in Book your vacation with us today!

A modern living area is presented with a neutral color scheme. A large, flat-screen television is mounted on the wall, accompanied by a cozy sofa and a small coffee table. A wooden dining table is positioned nearby with a simple vase, enhancing the functional space.

4.84 out of 5 average rating, 159 reviews

★Violeta★Luxury Private Rooftop in Old San Juan

Violeta is our apartment located in the heart of Old San Juan. From here you have access to over a dozen restaurants and world famous bars walking distance. Enjoy watching a movie on the living room or bedroom, working from home on our dedicated space or impress cooking or ordering food. Entire apartment is air-conditioned for your convenience. The apartment has a lovely rooftop that overlooks the Cathedral. Enjoy breathtaking sunsets, sit down and read a book or just chill at the jacuzzi.

Top guest favorite

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, 236 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.

A spacious bedroom features a large bed dressed in a plush grey coverlet. Glass sliding doors lead to a balcony with outdoor seating, allowing views of the cityscape. Soft lighting enhances the modern decor, while the sleek furnishings include a bedside table and decorative accents.

4.85 out of 5 average rating, 134 reviews

*Luxury PH-Apt* Best Location and Views* Wi-Fi,W/D

This PH unit have the best views of all San Juan from his spacious balcony, its located in La Placita area we’re all the bars, restaurants and night life are just a few steps away. The beach is just 10 mins walk and from (SJU) San Juan international airport it’s about 7-10 mins drive. The unit have Wi-fi and high speed internet and 2 T.V.s Free assigned parking in the same condo with control access. The Apt. is fully remodeled and equipped with all you will need to have a pleasant stay.

Top guest favorite

A charming garden pathway is illuminated by soft string lights, creating a serene setting. Lush tropical plants frame the walk, and a wooden table with chairs is positioned on the red tiled floor, inviting guests to relax in this peaceful outdoor space.

Guest suite in San Juan

4.94 out of 5 average rating, 303 reviews

Garden Oasis, Steps to the Beach

We are located steps from beautiful Ocean Park Beach. This 1 bedroom/1 bath 2nd floor apartment is nestled among tropical flowers, orchids and foliage. It includes an equipped kitchen, linens and a futon in living area - plus a new bathroom and A/C. The garden is gorgeous!!!! Coquis serenade you in the evening plus the fountain and wind chimes are devine. There are boogie boards, a kayak and even paddleball. Amazing restaurants and a variety of bars are just a block away on Calle Loiza.

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, 278 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, 139 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.

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, 239 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.