Discover Your Ideal Vacation Rentals in Port of Spain, San Juan-Laventille for a Memorable Trinidad and Tobago Getaway
Discover Your Perfect Port of Spain Vacation Homes
Best Vacation Homes in Port of Spain
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Child Friendly
- Parking
- Bedding/Linens
- Guest Services
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Wheelchair Accessible
- Security/Safety
- Bedding/Linens
- Wellness Facilities
- Air Conditioner
- Parking
- Pet Friendly
Port of Spain Luxury Rentals
- Air Conditioner
- Parking
- Pool
- Security/Safety
- Bedding/Linens
- Wellness Facilities
- Pool
- Wheelchair Accessible
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Balcony/Terrace
- Security/Safety
- Kitchen
- Security/Safety
- Bedding/Linens
- Wellness Facilities
- Air Conditioner
- Parking
- Pool
Port of Spain Pet Friendly Vacation Rentals
- Pet Friendly
- Security/Safety
- Child Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Pet Friendly
- Security/Safety
- Child Friendly
- Air Conditioner
- Pet Friendly
- TV
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Pet Friendly
- Security/Safety
Port of Spain Large Vacation Homes
- Air Conditioner
- Parking
- Pool
- Parking
- Pool
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
Why Choose Rent By Owner for your Port of Spain Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Port of Spain Vacation Rentals
Where are the best neighborhoods to stay in Port of Spain?
When exploring Port of Spain and the surrounding San Juan-Laventille area in Trinidad and Tobago, choosing the right neighborhood can greatly enhance your stay. Whether you prefer vibrant urban settings with easy access to downtown attractions or quieter residential areas for a more relaxed experience, this region offers diverse options to suit your preferences. Each neighborhood provides unique advantages, from convenient amenities to local charm, making it easier for you to find the perfect vacation rentals that meet your needs. Trust in reliable and seamless booking options to secure your ideal accommodation in this lively and culturally rich part of Trinidad and Tobago.
Downtown
Staying in the downtown area offers you convenient access to the cityโs vibrant business and cultural hubs, making it an ideal choice for exploring local attractions and enjoying the energetic atmosphere of Port of Spain.
View 102+ Rentals in DowntownSuccess
Located in the northern part of the region, Success provides a peaceful retreat while still being close to key amenities and transport links, perfect for experiencing authentic local life in San Juan-Laventille.
View 144+ Rentals in SuccessCocorite
This neighborhood is renowned for its scenic coastal views and relaxed environment, making it an excellent choice for those seeking a seaside escape within reach of Port of Spainโs attractions.
View 226+ Rentals in CocoriteBest Times to Visit Port of Spain
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here ensures you can fully enjoy the vibrant culture and pleasant weather, making your stay in Port of Spain, San Juan-Laventille, Trinidad and Tobago, truly memorable.
Peak Season Highlights
December to April
During the dry season, you'll enjoy warm weather and less rainfall, making it an ideal time for outdoor activities and exploring the vibrant local culture in Port of Spain.
June to August
This period marks the peak of the regional festival season, attracting visitors seeking lively events and celebrations in the area.
Off-Season Highlights
May to June
The shoulder months see a slight decrease in tourist activity, providing a more relaxed atmosphere for enjoying this bustling destination with fewer crowds.
September to November
As the region transitions into the wet season, you might encounter brief showers, but this is also an opportunity to experience the local lifestyle away from peak visitor levels.
Weekly Weather Forecast for Port of Spain
How to Book Your Port of Spain Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Port of Spain
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or terrace to unwind after exploring the regionโs vibrant culture.
- Take advantage of a well-maintained swimming pool, perfect for relaxing under the sun here.
- Benefit from lush gardens or landscaped yards that offer a peaceful setting during your stay.
- Look for outdoor dining areas or barbecue facilities to enhance your local culinary experience.
- Discover dedicated parking spaces or covered carports for convenient arrivals and departures.
- Some properties may include a balcony with scenic views of the surrounding landscape or city skyline.
- Access to nearby parks or outdoor recreational spaces for active pursuits during your visit.
Top Attractions Around Port of Spain
What attractions are nearby?
Explore the vibrant cultural experiences, lively markets, and scenic parks just moments away from your vacation rentals in Port of Spain, offering a perfect blend of relaxation and adventure in this dynamic region.

Family Activities
- Queen's Park Savannah: Enjoy a leisurely stroll or a family picnic in this expansive park that serves as the heart of the cityโs outdoor activities.
- Museum of Natural History and Science: Explore engaging exhibits that introduce you and your family to the rich biodiversity and scientific heritage of the region.
- Long Circular Mall: Experience a vibrant shopping and dining area perfect for a relaxed day out with the family, surrounded by local eateries and stores.
- Emancipation Monument and nearby parks: Discover historical landmarks and open green spaces ideal for cultural exploration and outdoor fun here in the area.
Adult Activities
- Queen's Park Savannah: Stroll through this expansive public park, enjoying its lush greenery and vibrant local events that showcase the region's lively culture.
- The National Museum and Art Gallery of Trinidad and Tobago: Explore the area's rich history and diverse art collections to gain a deeper understanding of this destinationโs cultural heritage.
- Royal Botanic Gardens: Relax amidst tropical flora at these beautifully maintained gardens, perfect for a peaceful retreat in the heart of the city.
- Palace of the Parliament: Discover the impressive architecture and learn about the regionโs political history during guided tours of this historic building.
Other Places to Stay in Port of Spain
Port of Spain Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Markets: Immerse yourself in the vibrant culture by visiting local markets, which offer authentic regional products and a glimpse into everyday life here.
- Experience Regional Cuisine: Make the most of your stay by sampling the regionโs unique culinary delights at nearby eateries and food stalls.
- Utilize Public Transportation: Take advantage of accessible public transportation options to easily navigate this destination and discover hidden gems around the area.
- Respect Cultural Etiquette: Enhance your visit by learning and observing local customs and traditions, ensuring respectful interactions during your stay here.
Transportation Options
- Public Buses: You can rely on the extensive bus network to conveniently explore the area, with routes connecting key neighborhoods and attractions.
- Taxis and Rideshare Services: Taxis and app-based rideshare options offer flexible transportation for quick trips across the region, ensuring comfort and safety.
- Car Rentals: Renting a car provides the freedom to discover hidden gems at your own pace within this destination and beyond.
- Private Chauffeur Services: For a more luxurious experience, private chauffeur services deliver personalized transportation tailored to your schedule and preferences.
Local Customs Options
- Carnival Celebrations: The region hosts vibrant Carnival festivities, where colorful costumes and lively music embody the local spirit and cultural pride.
- Steelpan Music: Listening to traditional steelpan music is a cherished custom here, reflecting the areaโs unique musical heritage and community gatherings.
- Local Cuisine Customs: Sampling dishes like doubles and roti offers insight into the area's culinary traditions rooted in Caribbean flavors.
- Market Traditions: Visiting bustling markets provides an authentic experience of the regionโs commerce and the importance of local trades and crafts.
Frequently Asked Questions About Port of Spain?
What are the top vacation rentals in Port of Spain?
There are a lot of options in Port of Spain. If you plan on staying in the Port of Spain area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Port of Spain:
- Shalom Guest House
- Stacys Place #1: 2 Bedroom Apartment
- Riverside Poolside Apartment
- Stacys Place #2: 2 Bedroom Apartment
- -20% Convenient Studio Queens Park Savannah Getway
- Sweet Stay
- Remodeled condo, minutes away from shopping centre
- BEAUTIFUL HOME IN PORT OF SPAIN TRINIDAD
- Garden Oasis 2: Villa with Private Pool
- The Cozy Corner at NorthHills
How many vacation rentals have private pools in Port of Spain?
There are 7 vacation rentals with private pools near Port of Spain. Top-rated RBO homes that have access to a swimming pool include:
Which vacation homes in Port of Spain are best for families?
If you are looking for a family-friendly vacation home in Port of Spain, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Port of Spain:
How many Rentbyowner vacation rentals are available in Port of Spain?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 269 in the Port of Spain area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Port of Spain.โฏ
Port of Spain Top Rated Vacation Rentals
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool