Whether you are planning a trip to San Juan for the San Sebastian Street Festival (SanSe), Puerto Rico TropiKal Half Marathon, or Saborea Puerto Rico, deciding where your “home base” will be is at the top of the list. Will you stay in one of the historic inns in Old San Juan, a beautiful beachfront spot in Condado, or a guesthouse in Santurce?
San Juan offers a dazzling array of places to stay so our team did some of the legwork to identify seven contenders. Read on for a varied selection of places to stay and several upcoming events in 2020.
The moniker of this capital city was originally given in the late 15th century when it was called San Juan Bautista after St. John the Baptist. In the early 1500s, it was renamed as San Juan, when Juan Ponce de Leon became the Spanish governor of the island.
It is these early beginnings that form what is now known as Old San Juan. The 500-year-old neighborhood is home to over 400 restored 16th and 17th century Spanish colonial buildings, narrow cobblestone streets, brightly painted homes, plazas, forts, beaches, parks, and a long roster of museums, including Museum of Contemporary Art of Puerto Rico and a book museum, Casa del Libro (House of the Book).
Hotel El Convento
If you’re looking for European-style classic luxury, then Hotel El Convento should meet your criteria. As its name suggests, this 370-year old landmark was originally built as a Carmelite convent and converted to a 58-room hotel in 1962. While it is the oldest member of the Historic Hotels of America, Hotel El Convento has modern amenities including a plunge pool, jacuzzi, 24-hour fitness center, onsite restaurant, beach club and more.
Accommodations are decorated with furnishings befitting the history of the building—handcrafted furniture, Andalusian tiled floors, and exposed mahogany beams. The brightly painted walls and colorful decor of the rooms instill a sense of warmth and invite you to relax and unwind.
Don’t just take our word for it. Hotel El Convento was ranked #4 in the Condé Nast Traveller 2019 Readers’ Choice Awards as one of the Best Hotels in the Atlantic, the Caribbean and Central America.
o:live Boutique Hotel
You will find o:live Boutique Hotel in the posh area of Condado in San Juan. It is a member of the Small Luxury Hotels of the World and features well-appointed suites that imbue a sense of “relaxed luxury and intimacy.” The hotel has an upscale steakhouse, rooftop bar and offers a curated list of tours and excursions for its guests. It is also the 2019 winner of the Condé Nast Johansens Best Small and Exclusive Hotel of the Americas.
The Dreamcatcher
The Dreamcatcher is a popular bed and breakfast committed to organic, low carbon footprint and locally sourced produce that it uses to prepare its famous breakfast and brunch. Self-dubbed as “San Juan’s only vegetarian hotel” and rooms with names like The Goddess, Bohemian and The Poet, this nine-room, three-suite retreat is just 200 steps from the beach.
Serafina Beach Hotel
Well-reviewed beachside mainstay Serafina Beach Hotel offers its guests an “exclusive lifestyle beachfront hideout” complete with floor to ceiling windows to take in the views, culinary journeys, modern bar with a master mixologist at its helm, and sleek and modern styled accommodations.
This hotel is also a 2019 winner of the Condé Nast Traveller Readers’ Choice Awards for one of the Best Hotels in the Atlantic, the Caribbean and Central America.
Upcoming events in San Juan
San Sebastián Street Festival (SanSe) | January 15-20, 2020
The San Sebastián Street Festival is an annual cultural festival held on Calle San Sebastián in Old San Juan, Puerto Rico. This family-friendly celebration brings locals and travelers together as they parade and celebrate in the streets with hundreds of artists, local musicians, food vendors and costumed revelers.
Puerto Rico TropiKal Half Marathon | March 1, 2020
Organized by a 100% local team of athletes and coaches with over 30 years of experience organizing local and international sporting events, Puerto Rico TropiKal Half Marathon is on track to become an internationally recognized event for veteran and novice runners looking to run, sun and have fun in one trip.
Afro Nation Puerto Rico | March 18-20, 2020
Afro Nation Puerto Rico is a music festival of the best artists in Afrobeats, hip hop, R&B, dancehall, reggaeton and bashment. Pulsating DJ sets complement this musical celebration held at Balneario de Carolina in Puerto Rico’s capital, San Juan.
Coffee and Chocolate Expo | March 28-29, 2020
Touted as the largest gastronomic event for coffee and chocolate lovers, the Coffee and Chocolate Expo in San Juan, Puerto Rico invites an estimated 19,000 participants to sample and enjoy coffee, chocolate, cookies, sweets, breads and other tasty treats from over 185 exhibitors.
Saborea Puerto Rico | April 2-5, 2020
Known as the premiere annual culinary event in Puerto Rico, Saborea Puerto Rico offers food connoisseurs the opportunity to savor the best in local cuisine and trendy gastronomic experiences.
La Concha Resort
Also located in the trendy Condado district, La Concha Resort offers guests twenty-first century “tropical modernism” with panoramic views and spacious and well-appointed rooms. Designed by celebrated local architects, the pet-friendly beach resort is also a popular nightlife destination.
352 Guesthouse
If your preference is a smaller, more intimate experience, try 352 Guest House. Housed in an 18th century building that was once a residence of a member of the military command of the Spanish Armada, this property has eight suites, each with its own private terrace and jacuzzi and an up close and personal view of the Atlantic Ocean, San Cristobal Castle, and other interesting sites.
This guesthouse’s small size certainly does not limit the experience. Guests can enjoy the rooftop deck, Puerto Rican cuisine at the onsite restaurant or relax in the underground wine cellar.
Nomada Urban Beach Hostel
Nomada Urban Beach Hostel is the first modern industrial style hostel in Puerto Rico. Room types range from four to ten bed dorms, semi-private or private rooms, deluxe rooms and even rooftop tents. This budget friendly option is well-reviewed for its friendly and attentive staff, rooftop patio, and its central location and easy access to San Juan hotspots and beaches.
This list of seven places to stay in San Juan is a small sample of the many types of hotels in this historically significant and culturally vibrant city. Let us know where you stayed in San Juan and what was your experience. Is your favorite San Juan hotel on this list? We would love to hear from you.