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 $696, price is now $556 per person
$556
per person
Jan 22 - Jan 26
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Price was $928, price is now $756 per person
$756
per person
Jan 22 - Jan 26
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $828, price is now $693 per person
$693
per person
Jan 22 - Jan 26
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
The Chancellor Hotel

The Chancellor Hotel

3 out of 5
Price was $784, price is now $656 per person
$656
per person
Jan 22 - Jan 26
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Regent Star Hotel

Regent Star Hotel

3 out of 5
Price was $744, price is now $636 per person
$636
per person
Jan 22 - Jan 26
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
A restaurant and an outdoor pool are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Free perks include cooked-to-order breakfast, free self parking, and an area shuttle.

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
$113 nightly
The price is $124 total per night
$124 total
Dec 15 - Dec 16
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.
SherNest Guest House

SherNest Guest House

3 out of 5
25 GORBIN #1 San Juan San Juan-Laventille Regional Corporation
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This bed & breakfast doesn't skimp on freebies - guests receive free self parking and a free airport shuttle. An outdoor pool and laundry facilities are also provided.
The Bey

The Bey

3 out of 5
43 Jogie Rd San Juan San Juan-Laventille Regional Corporation
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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.
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
$172 nightly
The price is $188 total per night
$188 total
Jan 11 - Jan 12, 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.
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
$207 nightly
The price is $226 total per night
$226 total
Dec 21 - Dec 22
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.
Radisson Hotel Trinidad

Radisson Hotel Trinidad

4 out of 5
Wrightson Road Port of Spain Trinidad
Free Cancellation
$173 nightly
The price is $189 total per night
$189 total
Dec 19 - Dec 20
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.
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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 $556. 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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