St. Augustine Vacations from $420

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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 $619, price is now $420 per person
$420
per person
Nov 3 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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
Save 100% on your flight
Price was $1,227, price is now $732 per person
$732
per person
Nov 3 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Port of Spain (POS)
9.2/10 Wonderful! (1,001 reviews)
Very Very Good Service and Staff

Reviewed on Aug 20, 2025

Cara Hotels Trinidad

Cara Hotels Trinidad

3 out of 5
Price was $918, price is now $674 per person
$674
per person
Nov 3 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Port of Spain (POS)
7.6/10 Good! (217 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

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Price was $917, price is now $688 per person
$688
per person
Nov 3 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Port of Spain (POS)
8/10 Very Good! (1,004 reviews)
Nice spot. Clean, quiet, great staff energy.

Reviewed on Aug 22, 2025

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
Price was $805, price is now $632 per person
$632
per person
Nov 3 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Port of Spain (POS)
7/10 Good! (30 reviews)
Overall. It was quiet and cozy.

Reviewed on Jul 13, 2025

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Discover the most popular places to visit in St. Augustine

Night Photography, Mount St Benedict Trinidad

Mount St. Benedict Monastery

5/5(1 review)

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

4/5(55 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

$80
per adult
Street Food and a Taste of Trinidad Night life
Caroni Wetlands Sunset Boat Tour

Caroni Wetlands Sunset Boat Tour

$70
per adult
94% of travellers recommend
Caroni Wetlands Sunset Boat Tour
Doubles Taste So Good!

Trinidad Nighttime Food Tour

$69
per adult
100% of travellers recommend
Trinidad Nighttime Food 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 Aug 24 to Aug 25
$119 total
Aug 24 - Aug 25
Total with taxes and fees
9.2/10 Wonderful! (44 reviews)
"What a special place to have stayed! The Pax Guest House is located atop Mount Saint Augustine in one of the nicest locations on Trinidad. Fantastic views from this well-preserved guesthouse that dates to 1925. Fantastic hosts manage this property. They are very helpful and reliable. The guesthouse ..."

Reviewed on Aug 7, 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
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
$261 nightly
The price is $284 total per night from Sep 17 to Sep 18
$284 total
Sep 17 - Sep 18
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Very Very Good Service and Staff"

Reviewed on Aug 20, 2025

Hyatt Regency Trinidad
See all 391 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.

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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 $420 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.