With two bedrooms and enough bed space to sleep six, consider this a major contender for your next group trip to San Juan. The pretty-in-pink interiors, dotted with blond wood furniture and beige decor, are soft and calming. Meanwhile the Bluetooth speaker-enabled home offers a private spot to practice your moves before a night out dancing. The terrace opens up to a patio with a hammock for lazing with a beach read. Plan for at least one night dining in via the outdoor grill and dining area, with the Santurce Farmers Market a short walk away for picking up supplies beforehand. From $263 per night.
Perks: Indoor fireplace, washer and dryer, pool, koi pond
Cayey is an hour’s drive away from San Juan for anyone who wants to keep the hustle of a metropolis at an arm’s length. This four-bedroom hillside villa with a lush outdoor space sleeps up to eight people, with enough bathrooms (four of them, not including a powder room) to ensure that no can complain about someone else hogging the mirror for too long. The rooms are decorated with African-inspired furniture and artwork for a safari-inspired escape, with massive windows and terraces that look out onto sweeping mountain views and of course the grounds themselves. Admire the swimming pool and hot tub, koi pond, and outdoor dining area from your perch indoors or experience it first-hand. From $1,200 per night.
Perks: Infinity pool, full kitchen, outdoor shower
Watching the sunrise and sunset should be on the itinerary for anyone who stays in this cabin surrounded by mountains. Start each day with a splash under the outdoor shower, preferably followed by a quick disco nap on the hammock (hey, waking up is hard). The best place to lounge is the neat “terrace” jutting out from the second floor. The location, a hidden spot in Isabela, definitely leans “off the grid” when it comes to vacation rentals. While it’s no oceanside house, you won’t see landscapes like these from your beach chair. From $239 per night.
Perks: Outdoor kitchen, private pool, outdoor shower, air conditioning
This single-bed dome is 10 minutes from the town of Cayey but the vibes are far from bustling. Best for nature lovers looking to disconnect (and reconnect), the small pool is the perfect spot for a post-breakfast dip. The outdoor shower is steps from the domed sleeping space housing a king-sized bed with views of the jungle and distant mountains. A fully equipped alfresco kitchen can handle breakfast, lunch, and dinner. From $298 per night.
Perks: Air conditioning, crib, beach chairs, and cooler
This historic villa is your best bet for a Puerto Rico Airbnb getaway that gets you up close with all the old world architecture of the city center, Old San Juan. Staying here is essentially a lesson in Puerto Rican art as the walls are covered in vibrant works from all corners of La Isla del Encanto, too. Plus, the interiors themselves have been renovated to preserve historic design touches such as arched windows, ornate doors, and sky-high ceilings. Plaza de Armas is a quick stroll away, as well as the never-ending nightlife of Calle San Sebastian. But don’t worry: The two-bedroom home is tucked away on a quiet street so you can still get in your beauty sleep before another day of exploring. From $490 per night.
Perks: Plunge pool, garden patio, air conditioning
