Old San Juan holiday rentals

We found 490 holiday rentals — enter your dates for availability
Discover a selection of 18 homes, 148 apartments and other holiday rentals in Old San Juan that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit Old San Juan for a holiday rental?
The best time to visit Old San Juan for a holiday rental is during the peak season from March to May, with March being particularly popular among travellers seeking vibrant cultural experiences and pleasant weather. This period sees an influx of visitors eager to explore the historical charm of the city, with its colourful historic buildings and rich history. The warm climate, typically ranging from 24 to 30 degrees Celsius, allows for comfortable outdoor activities, making it ideal for sightseeing and leisurely strolls along the picturesque streets.March, specifically, offers numerous festivals and events, providing a lively option that enhances the travel experience. You'll find plenty of opportunities to immerse yourself in local culture, from art exhibitions to gastronomic delights at various eateries throughout the area.For those looking for a more budget-friendly option, October presents a fantastic alternative. While this month falls within the low season, it offers the chance to enjoy a quieter Old San Juan. The weather remains warm, and you can explore the city's attractions without the crowds, allowing for a more relaxed experience.
What are the top attractions in Old San Juan, Puerto Rico?
In Old San Juan, visitors can take part in a rich tapestry of history and culture. The iconic El Morro Fortress offers breathtaking views of the Atlantic Ocean and is a must-see for anyone exploring the area. Nearby, San Cristóbal Fortress provides insight into the island's historic past and is surrounded by lush gardens great for a leisurely stroll.The vibrant streets of Old San Juan, characterised by cobblestone paths and colourful buildings, lead to the stunning Cathedral of San Juan Bautista, one of the oldest churches in the Americas. As you wander, you can discover charming plazas, such as Plaza de Armas, which is a great spot to relax and soak in the local atmosphere.Art enthusiasts will appreciate the Museo de Arte de Puerto Rico, located a short distance away, showcasing impressive collections of Puerto Rican art.
Are all fees included in the Old San Juan holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Old San Juan holiday homes with parking?
Stayz offers a wide selection of holiday homes in Old San Juan with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Old San Juan holiday homes?
You can find great discounts on holiday homes in Old San Juan on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Old San Juan holiday home booking on Stayz?
To find Old San Juan holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Old San Juan?
A long-stay holiday home in Old San Juan is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Old San Juan holiday home?
Book your Old San Juan holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Old San Juan?
Prices for holiday homes in Old San Juan vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Old San Juan to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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