Vacation rentals with outdoor seating in Viejo San Juan, San Juan Antiguo

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, 145 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, 189 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*)

4.94 out of 5 average rating, 144 reviews

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.

Home in San Juan

Design Villa w Garden & Jacuzzi | CASA FRIDA by DW

Fully restored Art Deco house in the historic Santurce neighborhood that boasts original creole tiles & geometric, stylized ornaments typical of its era. This short-term rental home mixes modern sensibilities to create a more streamlined, clean look. Look down to the bamboo garden from the roomy terrace while reclining in the hammock and dining alfresco. Built in the 40s, this upscale home features big walk-in rain showers, a hot tub, mid-century modern furniture, plus 2 terraces & 3 balconies.

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, 224 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, 247 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.

4.93 out of 5 average rating, 227 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.

Superhost

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.

4.84 out of 5 average rating, 127 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.

Shipping container in Gurabo

A spacious outdoor terrace features stylish black seating arrangements, including a sofa and accent chairs. A wooden table sits at the center, topped with a small plant. Lush greenery and distant panoramic views are visible, enhancing the tranquil atmosphere.

4.98 out of 5 average rating, 184 reviews

Vista Linda Haus

At Vista Linda Haus, from the moment you start the journey to the beautiful town of Gurabo, the adventure begins. A unique experience towards the favorite destination. You will find panoramic landscapes, lakes, mountains, farms, cities, and a community with the Puerto Rican warmth of our mountains. Just 35 minutes from the Luis Muñoz Marín International Airport, over 1,000 feet above sea level, you will breathe freedom and peace, in a harmonious environment full of energy and pure nature.

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, 296 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.

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, 136 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.

4.89 out of 5 average rating, 168 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.