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.
Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
9.2/10 Wonderful! (1,002 reviews)
This is my 4th stay at the Hyatt TT and it did not disappoint. The hotel itself is clean, comfortable and bright, I felt very safe there and I enjoy how vibrant and bustling the lobby is.

Reviewed on Jul. 2, 2025

Zenbreak The House of Praise

Zenbreak The House of Praise

2 out of 5
Save 100% on your flight
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
No reviews
Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
8/10 Very Good! (1,002 reviews)
I believe I paid Expedia for breakfast for two for two days but Hilton did not get that or honor it

Reviewed on Jun. 29, 2025

Woodbrook on the Avenue

Woodbrook on the Avenue

2.5 out of 5
Woodbrook
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
9/10 Wonderful! (66 reviews)
Cleanliness and comfort stood out. A very engaging team, especially Melissa!! One thing i would recommend is an upgrade to the door locks, feel the inside throw bolt or deadbolt is needed for a more secure feeling.

Reviewed on Oct. 20, 2024

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
7/10 Good! (29 reviews)
Great location in Port of Spain

Reviewed on May 7, 2025

Ready to book your vacation to St. Augustine?

 

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St. Augustine Hotel Deals

Pax Guest House
Pax Guest House
3 out of 5
Mount St. Benedict, St. Augustine, Trinidad
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jul 4 to Jul 5
CA $147
CA $161 total
Jul 4 - Jul 5
includes taxes & fees
9.2/10 Wonderful! (43 reviews)
"Lovely hosts, good breakfast, wonderful terrace wirh lots of hummingbirds."

Reviewed on Mar. 31, 2025

Pax Guest House
Hyatt Regency Trinidad
Hyatt Regency Trinidad
4.5 out of 5
No 1 Wrighton Road, Port of Spain, Trinidad
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from Jul 9 to Jul 10
CA $281
CA $339 total
Jul 9 - Jul 10
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Great people great times"

Reviewed on Jul. 1, 2025

Hyatt Regency Trinidad
Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG
Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG
3 out of 5
No 1 Exposition Drive, Piarco, Trinidad
Fully refundable
The price is CA $207 per night from Aug 3 to Aug 4
CA $207
CA $251 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Great staff, perfect hotel for a transit stay-over"

Reviewed on Jun. 30, 2025

Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG
See all 376 properties in St. Augustine
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in St. Augustine

University of the West Indies

4/5(4 reviews)

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

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
Trinidad: Mud Volcano Tour

Trinidad: Mud Volcano Tour

CA $158
per adult
Trinidad: Mud Volcano Tour
Avocat Waterfall & Beach Tour

Avocat Waterfall & Beach Tour

CA $158
per adult
Avocat Waterfall & Beach Tour
See all activities in St. Augustine

Frequently asked questions

How much does a St. Augustine vacation package cost?
Offering excellent value package deals from CA $1,014 on Expedia, you'll be pleasantly surprised at how much a vacation to St. Augustine costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to St. Augustine?
The off-season is the best time to travel to St. Augustine if you're trying to keep costs down. Another tip for finding cheap St. Augustine vacation packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for St. Augustine?
St. Augustine vacations come in various shapes and sizes, but to really sink your teeth into this destination, we think 3 days is a good ballpark. With this timeframe, you can fit in major attractions like Yerette - Home of the Hummingbird and Tunapuna Market and seek out some lesser-known gems. Don't skip cool areas such as El Dorado and Tacarigua either. If you plan wisely, you can even allow for a day trip from St. Augustine too.
How to find the best St. Augustine package deals?
Landing a cheap St. Augustine package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly St. Augustine package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a St. Augustine vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still get the flexibility to create a personalized St. Augustine vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to St. Augustine?
If you're considering a spontaneous St. Augustine adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to St. Augustine?

  1. Choose your dates: The things you'd like to do in St. Augustine and your preferred season will help you decide when to go.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to set aside for your trip to St. Augustine. Then, pick a hotel that suits your budget, whether that's an economical option or a lavish retreat.
  3. Decide how many days away: Start by listing all the sights and activities you want to get to in St. Augustine. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the perfect St. Augustine vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.