Holiday rentals with outdoor seating in Viejo San Juan

4.93 out of 5 average rating, 107 reviews

Home in San Juan

Casa Azul | Worry Free - Stay in Old San Juan

Colorful three-level home in the heart of Old San Juan. Located on Callejón El Tamarindo, this colonial-modern home sits within the historic district, surrounded by restaurants, nightlife, and cultural landmarks. Features a cozy private terrace ideal for sunny days or romantic evenings. The property includes a Tesla-powered backup system Plus 150-gal backup water cistern., providing comfort and peace of mind during power outages. A vibrant stay in one of Puerto Rico’s most iconic neighborhoods.

4.92 out of 5 average rating, 275 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 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.

4.81 out of 5 average rating, 181 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.

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.

4.83 out of 5 average rating, 173 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.

A private rooftop garden features a spacious seating area with a blue sofa next to a wooden coffee table. The area is adorned with decorative plants and a dining table surrounded by white chairs. Shade is provided by a black canopy overhead.

4.88 out of 5 average rating, 144 reviews

Apartment w/ Private Rooftop | Old SJ | Central AC

Enjoy a stylish experience at this centrally-located PRIVATE apartment with PRIVATE rooftop (no one else has access to unit or rooftop). It is located in the heart of Old San Juan on Sol (Sun) Street, right by most of the nightlife (bars and restaurants). The apartment is close to El Morro, the fort the Spanish Crown used to defend San Juan back in the day. The unit is for six guests, and having more guests is prohibited. Additional guests who stay against the rules pay $50 per night.

4.89 out of 5 average rating, 114 reviews

Retro 1BR w/ Disco Ball | MOOD HAUS by DW

Stay at MOOD HAUS by DW, a 70s-inspired boutique property in vibrant Santurce. Each uniquely designed suite features bold retro interiors, a private outdoor terrace, full kitchen, designer rain shower, vinyl player, record collection, and disco ball. Walk to the beach, restaurants, bars, and San Juan’s local art and nightlife scene. The property is equipped with a backup water cistern and generator to help provide additional support in the event of water or power outages.

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, 277 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.

4.95 out of 5 average rating, 232 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.

4.89 out of 5 average rating, 326 reviews

Borinquen Villa - Historic Old San Juan

This beautifully renovated condo with A/C throughout is truly a gem in historic Viejo San Juan. Located in the heart of Old San Juan, just off the lively Calle de San Sebastian and footsteps from El Morro, you're always within walking distance of a great time. Whether it's historic landmarks, great restaurants, trendy shops, or lively local bars, you're just a few minutes away.

5 out of 5 average rating, 131 reviews

A spacious bed is centered against a softly lit, curved wall. Woven pendant lights cast a warm glow above the bed, accompanied by decorative pillows. A cozy bench sits at the foot of the bed, while natural textures are visible in the surrounding furnishings.

Loft in Santurce

*NEW* Relax Outdoor Bathtub, Walk To Beach

Located in the heart of Puerto Rico's lively Calle Loíza, 8-10 minutes from the airport and 8 minutes walk to the beautiful "Ocean Park beach", "Palomar" at Casa Loiz offers an authentic Puerto Rican experience with access to beaches, restaurants, and bars within walking distance. Important cultural sites, such as Old San Juan, are only a 5-10 minute drive away.

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.

4.98 out of 5 average rating, 223 reviews

Villa Estrella PR (near Airport & Beach)

Diviértete con toda la familia en este alojamiento con estilo. Esta cerca de todo lo esencial como el Aeropuerto y Playas (5 minutos), Viejo San Juan, Plaza Las Américas (15 minutos). Localizado cerca de varios restaurantes con prestigio como Bebo’s BBQ, Metropol, y el área turística de Piñones donde podrán encontrar comida típica de nuestra isla.

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, 285 reviews

Old San Juan PH with Ocean View Private Terrace

Ocean Terrace Sanctuary in the Heart of Old San Juan Ocean-view terrace penthouse in the heart of Old San Juan. Sunrises, sea breeze, and silence above the city. Bright, air-conditioned loft with a king bed and a bookshelf that steals scenes. Third-floor walk-up (steep last flight), a short climb to another world.

Popular amenities for outdoor seating rentals in Viejo San Juan

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.9 out of 5 average rating, 278 reviews

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.

Home in Santurce

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

4.91 out of 5 average rating, 162 reviews

A modern living area features a curved plush sofa in a rich brown hue, paired with minimalist artwork on a textured wall. A warm wooden ceiling and soft lighting create a cozy ambiance, complemented by decorative objects on a nearby shelf.

Home in Santurce

Bright Close to the Beach | Dolçe Esterra | Solar

4.97 out of 5 average rating, 122 reviews

A serene outdoor space features a private pool surrounded by palm trees and vibrant seating. The clear water reflects the blue sky, while a lush green lawn extends toward a calm body of water in the background, enhancing the tranquil setting.

Home in Toa Baja

Lake Villa House in Toa Baja, Puerto Rico

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.

4.99 out of 5 average rating, 100 reviews

Lake View | King Beds | Battery Backup | Home Gym

Home in La marina Carolina

A modern interior space features an open layout with a sleek kitchen against one wall. A spacious living area is highlighted by a large television displaying an image of an airplane on a runway. Contemporary lighting offers bright illumination throughout.

4.93 out of 5 average rating, 105 reviews

Casa Helice 3 min from airport -Placas Solares-

A serene outdoor space features a private pool with tranquil blue water, surrounded by lounge chairs and lush greenery. An inviting seating area is visible, alongside a bar with high stools. A well-lit space creates an atmosphere for relaxation and enjoyment.

4.99 out of 5 average rating, 128 reviews

Villa Celestial Luxury Home

4.99 out of 5 average rating, 180 reviews

Hilltop Cabin w/ Pool & Views – 18 Mins to Airport

A private outdoor area is illuminated by string lights, creating a warm ambiance at night. The pool, featuring shimmering blue lights, is bordered by sleek lounge chairs. A modern barbecue grill is visible in the distance, surrounded by lush greenery and a clean, well-maintained pathway.

4.95 out of 5 average rating, 131 reviews

Casa Kenia

Apartment rentals with outdoor seating

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, 289 reviews

Best location with pool, steps from beach!

A bright living room features a light-colored couch adorned with patterned cushions. A wooden coffee table is positioned in front, complemented by a small decorative ottoman. Natural light filters through two window pairs with woven shades, and mid-century vintage decor enhances the inviting space.

4.95 out of 5 average rating, 115 reviews

Island Vibes · Steps to the Beach: Terrace/Balcony

A spacious living area is highlighted by a large sectional sofa in light fabric. A round ottoman adds seating flexibility, while a flat-screen TV is mounted on the wall. Natural light fills the space through large windows, and stylish décor elements contribute to the inviting ambiance.

4.76 out of 5 average rating, 108 reviews

Limón by VP - Apartment 4

The living area features a comfortable sofa and a television. French doors open to a terrace, allowing natural light and providing views of the surrounding area. Terra cotta tiles cover the floor, enhancing the room's authentic character.

4.85 out of 5 average rating, 126 reviews

La Bonita Rooftop Studio Apt

The family room features a large, cozy layout with a contrast of blue upholstery and a checkered tile floor. Artwork adorns the walls, while a ceiling fan offers comfort. Natural light enters through the open doorway, leading to a small balcony.

4.8 out of 5 average rating, 177 reviews

Historic Apartment | Old San Juan | Private Patio

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.

4.99 out of 5 average rating, 183 reviews

The Viewpoint @ The Cathedral in Old San Juan

A modern living area features a spacious white sectional sofa and a circular glass table. Natural light streams through sliding glass doors, which lead to a balcony. A large painting adorns the wall, complemented by soft lighting and minimalistic decor.

4.97 out of 5 average rating, 329 reviews

New gorgeous unit in Condado, San Juan near beach

4.93 out of 5 average rating, 327 reviews

The image features a view from a balcony overlooking Cristo Street at night. Cobblestone streets and parked cars are visible, with soft street lighting illuminating the historic buildings. Decorative plants and illuminated pallet furniture enhance the balcony ambiance.

Flat in Old San Juan

Old World Charm @the❤ofOSJ

Apartment rentals with outdoor seating

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, 135 reviews

Rare Beachfront Getaway w Pool, Gym, + Balcony!

An open-layout apartment is displayed, showcasing a comfortable white sofa, a round black coffee table, and a stylish blue chair. The sleeping area features a spacious bed with soft gray and white bedding, while natural light pours in through floor-to-ceiling windows adorned with sheer curtains.

4.91 out of 5 average rating, 242 reviews

⭐️Ocean View Apt. in Condado Beach & Strip⭐️

A bright living area features a light-colored sectional sofa paired with a round coffee table. Large sliding doors open to a balcony showcasing ocean views. The space is enhanced by a ceiling fan and a stylish mirror, while natural light highlights the ceramic flooring.

4.83 out of 5 average rating, 585 reviews

Luxury Oceanviews/ Condado / San Juan

A spacious terrace is shown, featuring a dining table and white chairs, with views of the turquoise sea and skyline. Lush greenery is visible along the edge, and a small lounge chair is placed for relaxation under partially covered awning, inviting enjoyment of the outdoor space.

4.93 out of 5 average rating, 123 reviews

Romantic Oceanfront Private Patio Full Generator

A spacious bedroom is presented with a queen bed dressed in white linens, complemented by light wooden furniture. A large window offers an ocean view, illuminating the room. A small desk with a chair and a dresser are also visible, enhancing the room's functionality.

4.98 out of 5 average rating, 134 reviews

Ashford Suite Ocean View Condado SanJuan W/Parking

A spacious room features a comfortable queen-sized bed with soft linens, complemented by a wooden accent wall. Natural light flows through large sliding glass doors, leading to a balcony with outdoor seating. A small desk with a red chair is positioned near the window.

4.91 out of 5 average rating, 459 reviews

**Perfect Location**

The kitchen area features a modern island countertop with a built-in stove and microwave. A sofa is positioned adjacent to large windows offering views of the city skyline. Abstract wall art adds a touch of color to the sleek design.

4.92 out of 5 average rating, 270 reviews

☀️LAGOON SIGHT APARTMENT San Juan☀️

A bright dining area features a long table with light-colored finish beneath a contemporary pendant light. Large windows showcase expansive ocean views, providing a backdrop of vibrant blue water and scattered clouds, while a potted plant adds a touch of greenery.