St. Augustine Vacation Packages
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Your St. Augustine Vacation
With one of our vacation packages to St. Augustine, you'll discover countless opportunities for fun and relaxation. There's tons to look forward to, including its rich history and beaches. Trincity Mall, University of the West Indies and Mount St. Benedict Monastery are just a few of the many attractions worth exploring during your trip to St. Augustine. Your ideal St. Augustine vacation is a couple of clicks away. Browse airfares, hotels and more on Expedia for a trip that's tailored to suit your travel style.
Top St. Augustine Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Chancellor Hotel
Price was CA $1,207, price is now CA $1,024 per person
CA $1,024
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Port of Spain (POS)
7.2/10 Good! (35 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
Hyatt Regency Trinidad
Downtown Port of Spain
Price was CA $1,516, price is now CA $1,288 per person
CA $1,288
per person
May 23 - May 27
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Port of Spain (POS)
9.2/10 Wonderful! (1,015 reviews)
Service was great and there was a lot of activities hosted by the hotel. Everyone was helpful and friendly. The hotel is conveniently located close to most attractions.
Reviewed on Apr 8, 2026
The Royal Hotel
Price was CA $1,590, price is now CA $1,357 per person
CA $1,357
per person
May 26 - May 31
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
7.8/10 Good! (48 reviews)
Had a small ant infestation and the rooms need to be updated, but it was clean. Staff was very friendly and helpful.
Reviewed on Mar 4, 2026
St. Augustine Hotel Deals
Pax Guest House
Mount St. Benedict St. Augustine Trinidad
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Apr 20 to Apr 21
CA $149
CA $164 total
Apr 20 - Apr 21
includes taxes & fees
Hyatt Regency Trinidad
No 1 Wrighton Road Port of Spain Trinidad
Fully refundableReserve now, pay when you stay
The price is CA $345 per night from Apr 26 to Apr 27
CA $345
CA $419 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
Service was great and there was a lot of activities hosted by the hotel. Everyone was helpful and friendly. The hotel is conveniently located close to most attractions.
Reviewed on Apr 8, 2026
Kapok Hotel
16-18 Cotton Hill St Clair Port of Spain Trinidad
The price is CA $169 per night from Apr 15 to Apr 16
CA $169
CA $209 total
Apr 15 - Apr 16
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
Pleasant stay, comfortable room
Reviewed on Apr 10, 2026
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.
Discover the most popular places to visit in St. Augustine
University of the West Indies
Walk around the campus at University of the West Indies during your visit to St. Augustine. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
What to do in St. Augustine
Port of Spain & Fort George Sightseeing Tour
CA $75
per adult
100% of travellers recommend
Full-Day City Tour, Maracas Bay & Caroni Bird Sanctuary
CA $157
per adult
100% of travellers recommend
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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.
