St. Augustine Vacations from $567

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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.

The Latest St. Augustine vacation packages

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 $759, price is now $567 per person
$567
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
9/10 Wonderful! (85 reviews)
Room was super clean and the staff was very courteous and helpful. The A/C worked just fine. I would stay here again

Reviewed on Jul 4, 2026

Airport Suites Hotel

Airport Suites Hotel

3 out of 5
Price was $817, price is now $583 per person
$583
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
6/10 (1,002 reviews)
Clean, Convenient, Cost Effective.

Reviewed on Jul 10, 2026

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
St. Anns
Price was $859, price is now $656 per person
$656
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
7/10 Good! (37 reviews)
Shower was not properly functioning when asked to switch rooms front desk could not program room key - they gave me access to a second room so I can shower using the housekeeping key both rooms had 1 towel 1 face towel and no washcloths Bar onsite but no staff to serve drinks Ended up checking out early due to issues at property

Reviewed on Apr 8, 2026

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $1,170, price is now $924 per person
$924
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
9.2/10 Wonderful! (1,047 reviews)
Great hotel.

Reviewed on Jul 11, 2026

Airport Inn

Airport Inn

3.5 out of 5
Price was $797, price is now $657 per person
$657
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
8.4/10 Very Good! (150 reviews)
Clean room and great breakfast

Reviewed on Jul 11, 2026

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Stay 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.
See properties

What to do in St. Augustine

Food Experience at Night

Food Experience at Night

$90
per adult
100% of travellers recommend
Food Experience at Night
monument in the middle of a park in Trinidad and Tobago

Half-Day Port of Spain Highlights & Maracas Bay Tour

$80
per adult
96% of travellers recommend
Half-Day Port of Spain Highlights & Maracas Bay Tour
Farmers' Market

Saturday Markets & Brunch Tour

$64
per adult
Saturday Markets & Brunch Tour
See all activities in St. Augustine

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
$108 nightly
The price is $119 total per night from Jul 13 to Jul 14
$119 total
Jul 13 - Jul 14
Total with taxes and fees
9.2/10 Wonderful! (51 reviews)
"Love of nature, peace and quiet and healthy food served at PAX will draw you to this ancient yet graciously kept guesthouse."

Reviewed on Apr 23, 2026

Pax Guest House
Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
No 1 Wrighton Road Port of Spain Trinidad
$249 nightly
The price is $276 total per night from Aug 7 to Aug 8
$276 total
Aug 7 - Aug 8
Total with taxes and fees
9.2/10 Wonderful! (1,057 reviews)
"Great hotel."

Reviewed on Jul 11, 2026

Hyatt Regency Trinidad
Kapok Hotel

Kapok Hotel

4 out of 5
16-18 Cotton Hill St Clair Port of Spain Trinidad
$150 nightly
The price is $165 total per night from Jul 13 to Jul 14
$165 total
Jul 13 - Jul 14
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
"Room clean, staff helpful, breakfast tasty."

Reviewed on Jul 11, 2026

Kapok Hotel
See all 445 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.

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

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Frequently asked questions

How much does a St. Augustine vacation package cost?
You can grab a vacation package to this popular destination from $567 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?

  1. Choose your dates: What you want to do in St. Augustine and your favorite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.
  5. Combine your airfare and accommodations: Once you've nailed down your dates and duration, book the right St. Augustine vacation package for you.
  6. 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.