Deals on vacations and trips to San Juan

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San Juan flight + hotel 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 $602, price is now $494 per person
$494
per person
Mar 19 - Mar 22
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Port Lodge

Port Lodge

3 out of 5
Price was $957, price is now $717 per person
$717
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Port of Spain (POS)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. You'll appreciate the area shuttle, garden, and laundry facilities.
Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $1,066, price is now $809 per person
$809
per person
Jan 30 - Feb 2
found 11 hours ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Price was $929, price is now $740 per person
$740
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
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.
Chaquacabana Resort & Beach Club

Chaquacabana Resort & Beach Club

3 out of 5
Price was $703, price is now $600 per person
$600
per person
Mar 19 - Mar 22
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
This Art Deco hotel features a private beach, a full-service spa, and a restaurant. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas. Enjoy the outdoor pool and unwind at the beach bar and poolside bar.

Top San Juan hotels deals

The Blue Mirage

The Blue Mirage

2 out of 5
Boundary Extension Road San Juan San Juan-Laventille Regional Corporation
$107 nightly
The price is $118 total per night
$118 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Dry cleaning is also provided.
Pool
Parking included
SherNest Guest House

SherNest Guest House

3 out of 5
25 GORBIN #1 San Juan San Juan-Laventille Regional Corporation
$112 nightly
The price is $123 total per night
$123 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
An outdoor pool is featured at this bed & breakfast, along with laundry facilities. Take advantage of the free self parking.
Pool
Parking included
The Bey

The Bey

3 out of 5
43 Jogie Rd San Juan San Juan-Laventille Regional Corporation
Get rates
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A picnic area and luggage storage are also provided.
Breakfast included
Parking included
Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
No 1 Wrighton Road Port of Spain Trinidad
Free Cancellation
Reserve now, pay when you stay
$227 nightly
The price is $248 total per night
$248 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
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.
Pool
Spa
Radisson Hotel Trinidad

Radisson Hotel Trinidad

4 out of 5
Wrightson Road Port of Spain Trinidad
Free Cancellation
$210 nightly
The price is $230 total per night
$230 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This traditional resort includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport shuttle. Unwind with a drink at the bar/lounge and enjoy perks like free self parking and a free area shuttle.
Pool
Parking included
The BRIX, Autograph Collection

The BRIX, Autograph Collection

4.5 out of 5
2-4 Coblentz Avenue Port of Spain Trinidad
Free Cancellation
Reserve now, pay when you stay
$217 nightly
The price is $236 total per night
$236 total
Jan 11 - Jan 12, 2026
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.

Frequently asked questions

How much are vacation packages to San Juan?
You can pick up an awesome flight and hotel bundle for as little as $494. With a Travelocity vacation package, a getaway in San Juan has never looked more enticing! Save both time and money and then get a start on packing those bags.
How long should my San Juan vacation be?
If you need some guidance, most visitors spend about 2 nights vacationing in San Juan. But to uncover the true essence of this place, stay a bit longer. You'll be able to explore more and really immerse yourself in the local vibe.
Where can I get the best vacation package deals for San Juan?
Look no further than Travelocity. With as many as 400 air carriers and 1,000,000 properties across the globe, it's easy to put together a San Juan package deal that suits your needs.
Why should I book my San Juan vacation bundle via Travelocity?
We take the stress out of travel planning. Whether you're seeking a new destination to uncover or want to ensure you get the best deal around, we've got you covered. Our 24/7 customer support, high-quality service and Price Match Guarantee mean you can book with confidence.
Can I save on my San Juan car rental if I book it with a hotel or flight?
You can with our San Juan vacation packages. With one of these, there are lots of ways to stretch your budget further. Bundle any two or more car, hotel, flight and tour bookings and watch your savings start to grow. With a rental car, all the popular attractions around San Juan are just a road trip away.
What is the best time of year to go to San Juan?
You'll score the cheapest hotel prices around and pay the most during . It's generally more relaxed in November, December and January, while there'll be more fellow travelers to hang out with during the months of June, September and October. It all depends on what you're willing to pay, the climate and how you deal with crowds.
Which airport is best for San Juan?
Many people arrive at Piarco Intl. Airport (POS). After you've disembarked and collected your luggage, head 9 mi northwest to reach central San Juan. A.N.R. Robinson Intl. Airport (TAB) is the other option available, 55 mi from the heart of the city.
Where should I stay when visiting San Juan?
If you're looking for a place to spend your nights, consider the Hislop On The Hill. It's the top pick for many visitors.

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