Search Deals on
St. Augustine Vacation Packages

Build your package with 2 more options

St. Augustine Flight + Hotel 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
Price was $852, price is now $602 per person
$602
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
Book a stay at this golf guesthouse in Port of Spain. Enjoy free WiFi, free parking, and a business center. Popular attractions Queen's Park Savanah and Ariapita Avenue are located nearby.
Best place for the price

Reviewed on Jul 13, 2026

Airport Suites Hotel

Airport Suites Hotel

3 out of 5
Price was $941, price is now $626 per person
$626
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
Book a stay at this business-friendly hotel in Piarco. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Millenium Golf Club and Trincity Mall are located nearby.

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
Price was $1,192, price is now $928 per person
$928
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
Book a stay at this business-friendly hotel in Port of Spain. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Queen's Park Savanah and Queen's Hall are located nearby.

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Price was $1,474, price is now $1,155 per person
$1,155
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
Book a stay at this luxury resort in Port of Spain. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Queen's Park Savanah and National Library and Information System Authority are located nearby.
It was great

Reviewed on Jul 18, 2026

Tstays Smart Hotel

Tstays Smart Hotel

2.5 out of 5
Price was $844, price is now $677 per person
$677
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
Stay at this hotel in Port of Spain. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Queen's Park Savanah and Ariapita Avenue are located nearby.
Short stay but ill rate 3/5. Room was cleaned tho

Reviewed on Jul 14, 2026

Metro Hotel Couva

Metro Hotel Couva

3.5 out of 5
Price was $851, price is now $690 per person
$690
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
Book a stay at this business-friendly hotel in Couva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Indian Caribbean Museum and Hanuman Murti Statue are located nearby.
I have no complaints

Reviewed on Jul 11, 2026

Airport Inn

Airport Inn

3.5 out of 5
Price was $910, price is now $739 per person
$739
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
Book a stay at this business-friendly B&B in Piarco. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Trincity Mall and Millenium Golf Club are located nearby.
Clean room and great breakfast

Reviewed on Jul 11, 2026

Regent Star Hotel

Regent Star Hotel

3 out of 5
Price was $1,062, price is now $868 per person
$868
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
Book a stay at this business-friendly hotel in Piarco. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Eco Park and Millenium Golf Club are located nearby.
All good

Reviewed on Jul 16, 2026

St. Augustine Vacation Packages 3-4 Night Stays

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 $782, price is now $605 per person
$605
per person
Aug 24 - Aug 28
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
Airport Suites Hotel

Airport Suites Hotel

3 out of 5
Price was $843, price is now $610 per person
$610
per person
Aug 24 - Aug 28
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
Tstays Smart Hotel

Tstays Smart Hotel

2.5 out of 5
Woodbrook
Price was $778, price is now $641 per person
$641
per person
Aug 24 - Aug 28
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
The Chancellor Hotel

The Chancellor Hotel

3 out of 5
St. Anns
Price was $911, price is now $754 per person
$754
per person
Aug 24 - Aug 28
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)

St. Augustine Vacation Packages 5-7 Night Stays

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 $852, price is now $602 per person
$602
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
Airport Suites Hotel

Airport Suites Hotel

3 out of 5
Price was $941, price is now $626 per person
$626
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
The Chancellor Hotel

The Chancellor Hotel

3 out of 5
St. Anns
Price was $1,192, price is now $928 per person
$928
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $1,474, price is now $1,155 per person
$1,155
per person
Sep 25 - Oct 1
found 17 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Copa
Sat, Sep 12 - Mon, Sep 28
MIA
Miami Intl.
POS
Piarco Intl.
$288 Roundtrip, found 1 hour ago
$288
Roundtrip
found 1 hour ago
Select Copa flight, departing Sat, Sep 12 from Miami Intl. to Piarco Intl., returning Mon, Sep 28, priced at $288 found 1 hour ago
Caribbean Airlines
Thu, Sep 24 - Thu, Oct 1
FLL
Fort Lauderdale - Hollywood Intl.
POS
Piarco Intl.
$323 Roundtrip, found 1 day ago
$323
Roundtrip
found 1 day ago
Select Caribbean Airlines flight, departing Thu, Sep 24 from Fort Lauderdale - Hollywood Intl. to Piarco Intl., returning Thu, Oct 1, priced at $323 found 1 day ago
Air Canada
Sun, Aug 9 - Tue, Aug 25
LGA
LaGuardia
POS
Piarco Intl.
$358 Roundtrip, found 1 hour ago
$358
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sun, Aug 9 from LaGuardia to Piarco Intl., returning Tue, Aug 25, priced at $358 found 1 hour ago
Air Canada
Sun, Sep 27 - Mon, Oct 12
YYZ
Pearson Intl.
POS
Piarco Intl.
$360 Roundtrip, found 1 day ago
$360
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Sep 27 from Pearson Intl. to Piarco Intl., returning Mon, Oct 12, priced at $360 found 1 day ago