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.
Woodbrook on the Avenue

Woodbrook on the Avenue

2.5 out of 5
Woodbrook
Price was CA $1,181, price is now CA $806 per person
CA $806
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
9/10 Wonderful! (73 reviews)
The property is gated, clean and secure. The rooms are well appointed, and supported by polite and personal support staff. There is also 24/7 security surveillance.

Reviewed on Jul. 3, 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was CA $1,612, price is now CA $1,198 per person
CA $1,198
per person
Nov 21 - Nov 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
9.2/10 Wonderful! (1,008 reviews)
Check in process was quick and efficient

Reviewed on Aug. 31, 2025

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Price was CA $1,773, price is now CA $1,353 per person
CA $1,353
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
8/10 Very Good! (1,005 reviews)
Nice spot. Clean, quiet, great staff energy.

Reviewed on Aug. 22, 2025

Cara Hotels Trinidad

Cara Hotels Trinidad

3 out of 5
Price was CA $1,442, price is now CA $1,128 per person
CA $1,128
per person
Nov 21 - Nov 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
7.6/10 Good! (219 reviews)
The staff were sympathetic and friendly. The pool area and deck are nice. The view is gorgeous 😍😍. I would give an average rating as I believe the rooms can do with some upgrades. Otherwise can be an ideal stay for families who want to take a vacation away from home.😃

Reviewed on Jul. 3, 2025

Radisson Hotel Trinidad

Radisson Hotel Trinidad

4 out of 5
Downtown Port of Spain
Price was CA $1,749, price is now CA $1,376 per person
CA $1,376
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
7/10 Good! (884 reviews)
Melissa very friendly. And the two budlers very friendly The female bar tenders is laking in customer service

Reviewed on Aug. 23, 2025

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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.

University of the West Indies

What to do in St. Augustine

Caroni Wetlands Sunset Boat Tour

Caroni Wetlands Sunset Boat Tour

CA $96
per adult
94% of travellers recommend
Caroni Wetlands Sunset Boat Tour
Street Food and a Taste of Trinidad Night life

Street Food and a Taste of Trinidad Night life

CA $110
per adult
Street Food and a Taste of Trinidad Night life
Doubles Taste So Good!

Trinidad Nighttime Food Tour

CA $95
per adult
100% of travellers recommend
Trinidad Nighttime Food Tour
See all activities in St. Augustine
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.