St. Augustine Vacation Packages 2026 from $671

St. Augustine flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Woodbrook on the Avenue

Woodbrook

$671

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Port of Spain (POS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.

Airport Suites Hotel

$684

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Port of Spain (POS)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Unwind with a drink at the poolside bar and enjoy perks like free self parking and a free area shuttle.

The Chancellor Hotel

St. Anns

$746

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Port of Spain (POS)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Relax with a drink at the poolside bar and enjoy perks like free self parking.

Hyatt Regency Trinidad

Downtown Port of Spain

$925

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Port of Spain (POS)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this luxury resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and perks like free self parking.

West Palm Hotel

$753

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Port of Spain (POS)

This hotel features 3 bars/lounges, a poolside bar, and a restaurant. Enjoy the outdoor pool and free perks like continental breakfast and free self parking. A coffee shop, free WiFi in public areas, and a grocery/convenience store are also on offer.

Top St. Augustine hotels deals

Pax Guest House

Mount St. Benedict St. Augustine Trinidad

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$119 total

Jun 23 - Jun 24

Total with taxes and fees

A restaurant and a gym are featured at this guesthouse. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Breakfast included

Parking included

Hyatt Regency Trinidad

No 1 Wrighton Road Port of Spain Trinidad

Free Cancellation

Reserve now, pay when you stay

$222 nightly

$246 total

Jul 3 - Jul 4

Total with taxes and fees

Pool

Spa

Kapok Hotel

16-18 Cotton Hill St Clair Port of Spain Trinidad

$140 nightly

$154 total

Jun 24 - Jun 25

Total with taxes and fees

This smoke-free resort includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.

Pool

Breakfast included

Hilton Trinidad & Conference Centre

Lady Young Road, Belmont Port of Spain

Free Cancellation

Reserve now, pay when you stay

$214 nightly

$233 total

Jun 25 - Jun 26

Total with taxes and fees

This luxury resort includes 2 restaurants, an outdoor pool, and an outdoor tennis court. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Pool

Hot Tub

Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG

No 1 Exposition Drive Piarco Trinidad

Free Cancellation

$170 nightly

$185 total

Jun 27 - Jun 28

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

The BRIX, Autograph Collection

2-4 Coblentz Avenue Port of Spain Trinidad

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$264 total

Jul 3 - Jul 4

Total with taxes and fees

This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Parking included

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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.

Popular places to visit

University of the West Indies

4/5(57 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.

Mount St. Benedict Monastery

5/5(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.

Frequently asked questions

How much are vacation packages to St. Augustine?

You can score a fantastic hotel and flight bundle for a mere $671. With a Travelocity vacation package, an escape to St. Augustine has never been more tempting! Save both time and money and then get a start on packing those bags.

How long should my St. Augustine vacation be?

Your St. Augustine break can be as long as you want, but many people stay about 3 nights. Can't wait to head off the beaten path and uncover some lesser-known sights? Stay an extra night or two and see another side of this place.

Where can I get the best vacation package deals for St. Augustine?

Picking up an amazing package deal to St. Augustine couldn't be easier with Travelocity. With as many as 400 air carriers and 1,000,000 properties all over the world, the choice is yours when picking your hotels and flights.

Why should I purchase my St. Augustine vacation bundle via Travelocity?

We've got experiences and destinations to suit every kind of traveler, excellent service and 24/7 support. And the icing on the cake is we'll match any lower price you're able to find with our Price Match Guarantee.

Will I save money on my St. Augustine car rental if I combine it with a hotel or flight?

Certainly. And our St. Augustine vacation packages are the perfect way to do it. In only a few clicks you can save cash and time by combining your bookings. Collect the keys to your rental car and do your vacation your way. Looking for things to do? Add some tours or experiences to your package and save on those too.

What is the best time of year to go to St. Augustine?

July, August and September is the most popular time to visit, while December, January and February tend to be less busy. If you're traveling with a limited budget, you'd be better off to visit around . is regarded as the dearest month to stay here.

Which airport is best for St. Augustine?

Piarco Intl. Airport (POS) is one place you can kick-start your St. Augustine getaway. About 6 mi southeast of St. Augustine, it welcomes travelers from all over each day. Another good option is A.N.R. Robinson Intl. Airport (TAB), 50 mi away from central St. Augustine.

What is there to do in St. Augustine?

St. Augustine is full of places to explore, like University of the West Indies and Mount St. Benedict Monastery. These two popular attractions are on most tourists' to-do lists.

Where should I stay when visiting St. Augustine?

If you're searching for someplace comfortable to lay your head, check out the Pax Guest House. It's the top choice for many travelers.