San Juan Vacation Packages
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Your San Juan Vacation
With everything planned before you go away, our San Juan vacation packages mean you can focus more on having fun. No matter if you're based in the neighborhood of Downtown Port of Spain, which is great for culture, or somewhere else, this city promises an array of discoveries. If your trip to San Juan includes a little sightseeing, check out popular attractions like Queens Park Savanah, Ariapita Avenue and Movietowne. Your San Juan vacation is clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored to suit your travel style.
Top San Juan Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Trinidad & Conference Centre
Price was CA $1,998, price is now CA $1,564 per person
CA $1,564
per person
Jun 10 - Jun 17
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
8.2/10 Very Good! (1,005 reviews)
Inside looks amazing, clean room , even friendlier staff who go the extra mile. Never ate food at the resort because we preferred to try the more local route but the drinks were on point.
Reviewed on May 10, 2026
West Palm Hotel
Price was CA $2,192, price is now CA $1,804 per person
CA $1,804
per person
Jul 19 - Jul 26
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Port of Spain (POS)
6/10 (120 reviews)
The receptionist was so welcoming and assisted us with breakfast when we couldn’t be there on time. Big up the chef for his delicious food, my child loves his fish in coconut milk and eggs 👍. Our room was generally clean and the environment as well together with, the fridge, microwave and Cable TV was in proper working condition. I would definitely recommend staying a night or two.
Reviewed on Mar 23, 2026
Tstays Smart Hotel
Woodbrook
Price was CA $1,410, price is now CA $1,178 per person
CA $1,178
per person
Jun 10 - Jun 17
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
9/10 Wonderful! (7 reviews)
Clean and Nice Room, very helpful staff, little noise in the evening due to the proximity of the hotel to the main road.
Reviewed on Mar 7, 2026
The Chancellor Hotel
Price was CA $2,075, price is now CA $1,747 per person
CA $1,747
per person
Jul 19 - Jul 26
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Port of Spain (POS)
7/10 Good! (37 reviews)
Staff was very friendly. The hotel is gated and always had someone available to open/close it. Check in and check out was a breeze. The hotel is within walking distance of a coffee shop, some local restaurants, the Savannah, gardens, zoo. There was no continental breakfast, no bar even though one was there. We didn't use the pool. Property could use some upgrades and renovation.
Reviewed on Apr 8, 2026
San Juan Hotel Deals
The Blue Mirage
Boundary Extension Road San Juan San Juan-Laventille Regional Corporation
The price is CA $138 per night from May 13 to May 14
CA $138
CA $167 total
May 13 - May 14
includes taxes & fees
10/10 Exceptional! (2 reviews)
The property was beautiful. The room was comfortable and met every need. Enjoyed the pool and the quiet. The neighborhood did not seem safe, and there were no restaurants in close proximity, so a car is needed. Recommend for those not wanting to stay in Port of Spain. Host and staff were gracious ...
Reviewed on Aug 1, 2025
SherNest Guest House
25 GORBIN #1 San Juan San Juan-Laventille Regional Corporation
The price is CA $114 per night from Jun 9 to Jun 10
CA $114
CA $137 total
Jun 9 - Jun 10
includes taxes & fees
8.8/10 Excellent! (3 reviews)
The space is great it needs updating though. I saw from last year other guests suggested a few things that would make a guest’s stay much more enjoyable but those things one year later has not been done. We stayed for carnival and the distance to events held in the Savannah was amazing. Message to ...
Reviewed on Feb 27, 2026
Cozy Bed & Breakfast Private Room
Santa Cruz San Juan
The price is CA $123 per night from May 12 to May 13
CA $123
CA $150 total
May 12 - May 13
includes taxes & fees
10/10 Exceptional! (1 review)
Pleasantly Suprised
This was our first visit to Trinidad and didnt know what to expect. Upon arrival we were happy to see that this was a beautifully secluded neighborhood. Our host Wendy was amazing and communicated with us throughout our stay. I recommended this Cozy bed and breakfast. You won't regret it!! ...
Reviewed on Jan 14, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
