Smoking-friendly holiday rentals in Viejo San Juan

Cozy studio close to Bad Bunny /Beach

* Book with confidence, this listing is 100% legal. New local regulations prohibit short term rentals in condos. Property in the most central location of San Juan, only a 7 minute walk from Ocean Park, the most popular beach of San Juan, and just a block away from great restaurants, bars and supermarkets. Easy 30 min drive from El Yunque Rainforest, and nice option if you are taking a cruise from San Juan, just 10 min drive from ship ports. Easy self check-in with keypads so no keys needed.

Modern Open Space Garden Apartment in Ocean Park

This property is a cozy retreat after a long day at the beach (just 3 minutes away!), with its own lush tropical garden and close proximity to everything you need within walking distance. This tropical and modern one-bedroom-garden apartment, is situated in the heart of a beach community in San Juan, Ocean Park, which is right next to the tourist zone of Condado, and half a block away from la Calle Loiza, a zone known for its cultural diversity and the renaissance of gastronomy in the city.

Gem on Popular Street in OSJ. Nightlife/Historical

EXTREMELY GOOD LOCATION. EVEN LOCALS ADORE IT! Look up SAN SEBASTIAN ST. It's right on the block, but quiet! Sumptuous 2 bedroom/1 bath apartment in the heart of Old San Juan.BEST BARS IN TOWN without compromising your peace and comfort. Bad Bunny just opened his new bar next to us. 5 BEDS TOTAL. This residence with central A/C & hot water has also great Wi-Fi and workspace. Closest to Plaza San Jose and steps away from all popular historical sites like El Morro, Fort San Cristobal etc.

Balcony + King Bed @La Placita | Free Parking

Apartment next to ‘La Placita’ in Santurce, the best area to stay in San Juan! Just steps from great restaurants and cocktail bars for any budget. The best spot to stay for Bad Bunny’s residence concerts! Walk to the beach, Condado Lagoon, and Miramar. Just 10 minutes drive to the airport, Old San Juan, and Isla Verde. We provide everything you need – just bring your outfits and get ready for a great time! Capture the murals by local artists for your perfect Insta shot, and tag us!

Cool Cozy Caribbean Oasis

PRIVATE UNIT APARTMENT with PRIVATE ENTRANCE that's next to my home. Equipped with a powerful Central Air condition with 1 Bedroom w/QUEEN SIZE MEMORY GEL FOAM BED & Living Room w/QUEEN SIZE MEMORY FOAM SOFA BED Plenty of amenities to keep you comfortable with everything needed for a cozy vacation oasis! Free street parking and a 10 min. walk to Isla Verde beach, fast foods, sport bars, restaurants and Supermarket. Hotels, Casinos, Condado, Old San Juan & 6 other beaches very close by.

La Garita Ocean View at Old San Juan

Charming ocean view one-bedroom apartment in the heart of Historical Old San Juan, right next to the iconic 16th-century Castillo San Cristobal. Fully equipped with AC, WIFI, a full-size bed, laptop desk, and a futon in the living room, this cozy apartment is ideal for a comfortable stay. Walking distance to supermarkets, shops, museums, cafes, and restaurants, it offers the perfect mix of history and convenience for your San Juan adventure.

Luxury waterfront villa with dock and heated pool

Villa Jade is a unique luxury waterfront retreat with a heated saltwater pool, jacuzzi, and private dock to a serene lagoon. It is just 10 minutes from SJU Airport and the fabulous beaches of Isla Verde. Three spacious bedrooms with private baths. Fully remodeled. Equipped with a generator and cistern for peace of mind. As a dedicated 5-star host, I’m here to ensure a smooth, relaxing stay. Welcome!

La Bonita Roof Top Studio Apt

Roof top studio suite with kitchen in authentic Spanish colonial architectural building in the center of the old town. The space opens to a terrace on two sides with incredible views. Very private. "Flexible check in" means check in: 10 am to midnight. Overnight check in if night is paid. STREET NOISE. DO NOT RENT THIS APT IF YOU ARE SUSCEPTIBLE FOR NOISE.

Penthouse with Private Rooftop!

Enjoy the National Historic Landmark District of Old San Juan in our 3 Bed, 2 Bath Colonial style Pent-House. Located on popular “Calle de San Sebastian”, our building is a page from history. Once known as the home of the fraternal organization "Respetable Logia de Caballeros', this space will surely take you back in time.