1,525 San Juan Holiday Homes

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Compare San Juan holiday homes from 11 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $25 to $1200 a night.

Information about San Juan

About San Juan

The bustling capital city of Puerto Rico (Rich Port) possesses one of the biggest natural harbors in the world and is also known as the second oldest European-founded city in the Americas. Besides being the center of the country’s financial capital and being ranked number one in the Caribbean for its shipping center, San Juan is also known as la ciudad amurallada, (the walled city). It is a destination that has it all, from paradise-like beaches, forts, museums, gardens, and churches to vibrant nightlife.

Things to Do in San Juan

If you’re visiting Old San Juan, there is a free trolley service that will get you around the city. Some of the most popular things to do and see include Plaza de Colon (you’ll find a variety of Christopher Columbus statues) as well as the Plaza de San Jose. Plaza de Hostos is also a popular square and is renowned for its artisan displays as well as its authentic Puerto Rican gastronomy. Any tour of Old San Juan would not be complete without visiting El Morro and La Fortaleza forts. These giant walls and forts are the primary reason why San Juan is referred to as the walled city and is characterized by its ramparts and cannons.

The island’s top beaches include Escambron Beach which offers you crystal clear water and hundreds of palm trees. Ocean Beach Park is less crowded and offers a more laid back vive between Isla Verde and Condado. Playa Peña is a secret beach where you can get away in a more intimate environment. Isla Verde Beach is an upscale and stylish seaside, which is to Puerto Rico, what Ipanema Beach is to Rio de Janeiro. Condado is the perfect beach for water activities including paragliding. Finally, Punta Las Marias is the premier location for windsurfers in San Juan.

San Juan Day Trips

One of the benefits of being the capital city of a relatively small island is the ease in which you can visit other neighboring areas. Just a couple of miles outside of San Juan, you will find Pinones which is a relaxing site where you can kayak, paddle board, and enjoy its wildlife. Popular food kiosks surround the site and here you can taste some of Puerto Rico’s staple dishes including mofongo (mashed plantains). 30 miles outside of the city, you’ll find the beautiful beach community of Luquillo which is known for its shallow and warm water. Here you will find resorts amenities for you and your family to enjoy. El Yunque, a national rainforest with a dense green oasis offers an astonishing waterfall and an escenic panorama. Having a free admission, is a must-see on the daily trips. Playa Santa and Cana Gorda are beach communities located in the southwest region of Puerto Rico and are reknowend for their pristine beaches and are warm year round with beautiful white sand. Other popular neighboring communities include Rio Piedras, Hato Rey, Saturce, and Puerta de Tierra.

San Juan Transportation

Moving around San Juan is relatively easy, as it is a walkable city. The city also has a robust bus system (the city has designated bus streets) and protected bike lines. The city owns a slight rail line and taxi rides are inexpensive. The best area to walk around is definitely Old San Juan.

Vacation Rentals in San Juan

Find the best San Juan vacation rentals with Tripping.com. Choose from 1545 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $1200 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 1195 of homes in San Juan offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 503 rentals with pool or jacuzzi, or relax with the family in one of the 1080 homes with cable TV.

For all those dog lovers and cat lovers, San Juan offers 173 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 11 rental sites in San Juan where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 720 HomeAway rentals, 484 TripAdvisor short term rentals and 247 Booking.com vacation rentals.