St. Augustine Vacations from $389
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest St. Augustine vacation packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Trinidad
Downtown Port of Spain
$795
per person
Nov 6 - Nov 10
found 19 hours ago
Roundtrip flight included
Bridgetown (BGI) to Port of Spain (POS)
9.2/10 Wonderful! (1,068 reviews)
The hotel was very nice. After arriving, I contacted the hotel to see if there was shuttle service. Spoke to Amit who stated the roads were flooded and it would be about 1 1/2 hours before they can send someone. We decided to take taxi service instead. Arrived, we were greeted and checked in by Amit. He was very knowledgeable and polite. The first room we were given, the window was frosted and we couldn’t see out. Even though the hotel was booked, he managed to move us to a room overlooking the water. Most of the staff was very friendly and eager to help. This included Daniel who assisted us to our room, Anoshka, Terysha, and Gillian who worked in the Regency Club. The Spa employees were excellent. Unfortunately there was others that were not as friendly or helpful. But I won’t bother mentioning them. We also enjoyed the pool and the Bar seating by the water
Reviewed on Aug 27, 2026
Don't see what you're looking for?
See all available trips from Columbus to St. Augustine
View all tripsStay near popular St. Augustine attractions
Mount St. Benedict Monastery
10.0/10 (1 review)
After visiting Mount St. Benedict Monastery, make a plan to see the other sights and activities in St. Augustine. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
What to do in St. Augustine
Half-Day Port of Spain Highlights & Maracas Bay Tour
$80
per adult
96% of travellers recommend
St. Augustine Hotel Deals
Pax Guest House
Mount St. Benedict St. Augustine Trinidad
Fully refundableReserve now, pay when you stay
$108 nightly
$119 total
Aug 29 - Aug 30
Total with taxes and fees
9.2/10 Wonderful! (55 reviews)
"This is one of the most unique places to stay in the Caribbean. It is worth staying just to visit the trails and be on the beautiful grounds next to the monastery."
Reviewed on Aug 8, 2026
Hyatt Regency Trinidad
No 1 Wrighton Road Port of Spain Trinidad
Fully refundableReserve now, pay when you stay
$246 nightly
$275 total
Sep 11 - Sep 12
Total with taxes and fees
9.2/10 Wonderful! (1,072 reviews)
"The hotel was very nice. After arriving, I contacted the hotel to see if there was shuttle service. Spoke to Amit who stated the roads were flooded and it would be about 1 1/2 hours before they can send someone. We decided to take taxi service instead. Arrived, we were greeted and checked in by Amit. ..."
Reviewed on Aug 27, 2026
Kapok Hotel
16-18 Cotton Hill St Clair Port of Spain Trinidad
$170 nightly
$188 total
Sep 5 - Sep 6
Total with taxes and fees
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.
Find the Best St. Augustine Vacation Packages
St. Augustine Essential Information
Language | English |
|---|---|
Currency | Trinidad and Tobago dollars |
Closest Airport | Piarco Intl. Airport (POS) |
Max Temp Winter | 80ºF |
Max Temp Summer | 85ºF |
Top Sights | Blanchisseuse Beach, Cleaver Woods Park and Lalaja Falls |
More vacations you might like
Frequently asked questions
How much does a St. Augustine vacation package cost?
You can grab a vacation package to this popular destination from $389 on Expedia. However, how much your vacation to St. Augustine costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to St. Augustine?
You can typically find lower prices and better availability in December, January and February. Check out our cheap St. Augustine vacation packages and you could land some great off-season discounts.
How many days is enough for St. Augustine?
Generally, a handful of days is enough to check out the top sights during your St. Augustine vacation. But if you want to have time to kick back or go on day trips, think about extending your trip.
How to find the best St. Augustine package deals?
Bagging a cheap St. Augustine package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly St. Augustine package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally 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 flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized St. Augustine vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to St. Augustine?
If you're planning a spontaneous St. Augustine trip, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to St. Augustine?
- Choose your dates: What you want to do in St. Augustine and your favorite season can help you decide when to travel.
- Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to airfares and activities. Your hotel will probably be the biggest expense during your trip to St. Augustine.
- Use Expedia's trip planning tool to explore St. Augustine: Research every part of your trip to St. Augustine with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
- Set the duration of your trip: Start by listing all the sights and activities you'd like to get to in St. Augustine. Then, estimate how long you'll need at each, including any travel time.
- Combine your airfare and accommodations: Once you've nailed down your dates and duration, book the right St. Augustine vacation package for you.
- Add on experiences and excursions: Read our travel guide to find some fun things to do in St. Augustine in St. Augustine. Book tickets or make reservations in advance to save time and avoid the hassle of searching for activities when you arrive.
Does Expedia offer Book Now, Pay Later St. Augustine vacation packages?
Your St. Augustine break is meant to be an escape from your busy life, not a source of money worries. So to allow you a little more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.