St. Augustine Vacations from $333

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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 $453, price is now $333 per person
$333
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Bridgetown (BGI) to Port of Spain (POS)
9/10 Wonderful! (76 reviews)
Staff greeted me warmly and guided me to my room where I was able to store my luggage for a couple of hours. Room was clean, had wifi, air-conditioning, and hot water. I'm very happy with my stay.

Reviewed on Oct 28, 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $1,281, price is now $963 per person
$963
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
9.2/10 Wonderful! (1,008 reviews)
The staff were efficient and friendly. The room is very nice and big and the sushi was great! Parking was a breeze

Reviewed on Jan 8, 2026

West Palm Hotel

West Palm Hotel

3 out of 5
Price was $1,235, price is now $1,036 per person
$1,036
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
6/10 (99 reviews)
No complaints from me whatsoever looking forward to visiting again

Reviewed on Dec 8, 2025

Regent Star Hotel

Regent Star Hotel

3 out of 5
Price was $1,526, price is now $1,283 per person
$1,283
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
6.8/10 (340 reviews)
Prompt professional front desk service. Reliably shuttle service.

Reviewed on Jan 7, 2026

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Price was $1,994, price is now $1,735 per person
$1,735
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
8.2/10 Very Good! (1,001 reviews)
Room was in good condition

Reviewed on Jan 3, 2026

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Discover the most popular places to visit in St. Augustine

Night Photography, Mount St Benedict Trinidad

Mount St. Benedict Monastery

Find out about the history of St. Augustine when you take a trip to Mount St. Benedict Monastery. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.

Mount St. Benedict Monastery

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

Farmers' Market

Saturday Markets & Brunch Tour

$64
per adult
Saturday Markets & Brunch Tour
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
Food Experience at Night

Food Experience at Night

$90
per adult
Food Experience at Night
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 Jan 11 to Jan 12
$119 total
Jan 11 - Jan 12
Total with taxes and fees
9.2/10 Wonderful! (46 reviews)
Pax Guest House is in a heritage building so it is important to know that some of the facilities are older. This did not impede our stay but it is something that visitors should be aware of before arriving. Both Gerard and Oda were wonderful hosts and made our time in Trinidad that much better. Gerard ...

Reviewed on Dec 12, 2025

Pax Guest House
2 Bed parking gated modern

2 Bed parking gated modern

2 out of 5
Gordon St, 27 St. Augustine Tunapuna-Piarco
10/10 Exceptional! (2 reviews)
Everything was great, thank you ! I think the battery in the gate opener msu need replacing.

Reviewed on Oct 29, 2025

Get rates
2 Bed parking gated modern
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
$263 nightly
The price is $287 total per night from Feb 1 to Feb 2
$287 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (1,009 reviews)
Fresh breakfast

Reviewed on Jan 2, 2026

Hyatt Regency Trinidad
See all 394 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 $333 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.