San Juan holiday lettings

We found 273 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in San Juan that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • 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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your San Juan getaway

The parks and other outdoor surroundings create an inviting atmosphere in San Juan. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around San Juan

Are you looking for attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that San Juan has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Yerette - Home of the Hummingbird (3.8 mi / 6.1 km)
  • Emperor Valley Zoo (4.5 mi / 7.3 km)
  • Millenium Golf Club (7.3 mi / 11.8 km)
  • Chaguaramas Golf Course (12.5 mi / 20 km)
  • Nariva Swamp (16.9 mi / 27.2 km)

Exploring the natural landscape of San Juan

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in San Juan. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Yerette - Home of the Hummingbird (3.8 mi / 6.1 km)
  • Queen's Park Savanah (4.1 mi / 6.6 km)
  • Maracas Beach (7.6 mi / 12.3 km)
  • Las Cuevas Beach (9.5 mi / 15.3 km)
  • Asa Wright Nature Centre (11.6 mi / 18.7 km)
  • Blanchisseuse Beach (14.5 mi / 23.4 km)

Transport to and around San Juan

Fly into Port of Spain (POS-Piarco Intl.), the closest airport, located 8.5 mi (13.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in San Juan when booking a holiday rental?
When considering the best area to stay in San Juan, Trinidad and Tobago for a holiday rental, the neighbourhood of San Juan itself offers a vibrant mix of local culture and accessibility. This area is known for its friendly atmosphere and is conveniently located near several attractions.

One of the highlights is the magnificent Church of the Holy Trinity, an impressive architectural gem that provides insight into the local history and culture. Additionally, the nearby Emperor Valley Zoo is a lovely spot for families and animal lovers, showcasing a variety of wildlife in a beautifully landscaped setting.

San Juan has a range of properties available for holiday rentals, suiting different budgets and preferences. Staying here not only allows you to immerse yourself in the local vibe but also provides easy access to other parts of Trinidad, making it an excellent base for exploration.
How much does it cost to rent a holiday home in San Juan?
Prices for holiday rentals in 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in San Juan to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for San Juan holiday house rentals?
You can find great discounts on house rentals in San Juan on Vrbo, 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.
What is the most popular type of holiday rental accomodation in San Juan?
In San Juan, apartments are the most popular type of holiday rental, with around 26 available in various neighbourhoods, providing convenient access to local attractions. These apartments typically come with amenities such as fully equipped kitchens, comfortable living areas, and often air conditioning, making them suitable for both short and extended stays.

In addition to apartments, there are several holiday houses offering more spacious rooms, ideal for families or larger groups. These houses usually feature multiple bedrooms, private gardens, and outdoor spaces for relaxation, allowing guests to enjoy the tropical climate.
Are there any family house rentals in San Juan?
In San Juan, Trinidad and Tobago, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. Many of these homes are situated in vibrant neighbourhoods such as St. Ann's and Port of Spain, offering both comfort and convenience.

Properties in these areas typically feature spacious living rooms, fully equipped kitchens for family meals, and outdoor spaces for kids to enjoy. Visitors can also find amenities like Wi-Fi and air conditioning, ensuring a pleasant stay.

Moreover, families can explore nearby attractions such as the beautiful Queens Park Savannah, ideal for picnics and leisurely strolls, or venture a bit further to the historical Fort George, which provides stunning views of the surrounding landscape.
Can I rent a holiday home with a pool or hot tub in San Juan?
In San Juan, Trinidad and Tobago, there are several holiday homes available for rent that feature pools and hot tubs, providing a fantastic option for travellers seeking relaxation. The vibrant neighbourhoods of Condado and Isla Verde are particularly popular for these types of accommodations, offering easy access to beautiful beaches and local amenities.

Many of these properties come equipped with inviting outdoor spaces, including private pools and hot tubs, ideal for unwinding after a day of exploring. Additionally, travellers can expect fully equipped kitchens, spacious living areas, and some rentals may even include barbecue facilities, making them superb for entertaining or enjoying family meals.
Can I find long-stay holiday rentals in San Juan?
A long-stay holiday rental in 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in San Juan?
In San Juan, Trinidad and Tobago, there are several pet-friendly house rentals available for those travelling with furry companions. Many of these properties are situated in convenient locations, offering easy access to local attractions and beautiful beaches. Travellers can expect amenities such as private gardens, spacious living areas, and fully equipped kitchens, making them comfortable for both humans and pets.

The area around the historic district of Old San Juan is particularly appealing, with its vibrant setting and close proximity to pet-friendly parks and outdoor spaces. Here, visitors can explore the charming streets and enjoy the local culture while having their pets by their side. Additionally, the nearby beaches often welcome leashed dogs, allowing for enjoyable days in the sun and surf.
Are there any remote work holiday rentals in San Juan?
In San Juan, Trinidad and Tobago, there are plenty of remote work-friendly holiday rentals available, with around 26 options to choose from. These accommodations cater well to those needing to balance work and leisure, offering amenities such as free Wi-Fi in rooms, dedicated desks, and comfortable chair setups to create an efficient workspace.

Many of these rentals are centrally located, providing easy access to local attractions like historical sites, beautiful beaches, and vibrant markets. This allows remote workers to enjoy the rich culture and stunning scenery of San Juan during their downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any San Juan holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in 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 on Vrbo 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.
What are popular rental amenities in San Juan?
In San Juan, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals and enjoy the local cuisine at their leisure. Many rentals also offer onsite parking, making it convenient for those who wish to explore the area by car. Additionally, travellers can expect outdoor spaces such as decks or patios, superb for relaxing in the warm Caribbean breeze. For those needing to work or study during their stay, many properties come equipped with a desk and chair, providing a comfortable workspace.
When is the best time to visit San Juan for a holiday rental?
September is the most popular month to visit San Juan, Trinidad and Tobago, as it offers an attractive blend of warm weather and vibrant local culture. This month falls within the peak season, which spans from July to September, making it an ideal time for those looking to immerse themselves in the lively option of the island. Visitors can enjoy outdoor activities, such as exploring the stunning beaches, engaging in water sports, or simply relaxing in the sun.

During this peak season, temperatures typically range from 25 to 32 degrees Celsius, creating a pleasant climate for sightseeing and outdoor adventures. The warm weather is great for enjoying the rich history of San Juan, including the impressive forts and colourful historic architecture.

For those who prefer a quieter experience, October presents a fantastic opportunity to visit San Juan at a more budget-friendly price. This time of year sees fewer tourists, allowing for a more relaxed exploration of the island's beauty and charm without the crowds.
How early should I book a San Juan holiday rental?
Book your San Juan holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in San Juan?
In San Juan, Trinidad and Tobago, visitors can immerse themselves in a variety of attractions that showcase the island's rich culture and natural beauty. The historic area of Port of Spain is a must-visit, where the vibrant streets are filled with historic architecture, markets, and the iconic Queen's Park Savannah, superb for leisurely strolls. Nearby, the Magnificent Seven, a group of stunning historic mansions, offers a glimpse into the island's past.

For those interested in local history, the National Museum and Art Gallery provides fascinating exhibits about Trinidad's heritage and artistic expressions. The vibrant neighbourhood of San Fernando is known for its lively option and the bustling San Fernando Hill, which offers panoramic views of the city and surrounding landscapes.

Nature enthusiasts should not miss the nearby Asa Wright Nature Centre, a beautiful rainforest reserve where visitors can observe diverse wildlife and enjoy guided tours through the lush surroundings.
Can I change or cancel my San Juan home rental booking on Vrbo?
To find San Juan holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the San Juan holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.