San Juan Vacation Packages 2025/2026 from $550

San Juan flight + hotel vacation packages

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

Woodbrook on the Avenue

Woodbrook

per person

Sep 14 - Sep 20

found 24 hours ago

Roundtrip 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. A business center, a terrace, and a garden are also on offer.

Hyatt Regency Trinidad

Downtown Port of Spain

per person

Aug 22 - Aug 26

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Zenbreak The House of Praise

Save 100% on your flight

per person

Sep 14 - Sep 20

found 24 hours ago

Roundtrip flight included

New York (JFK) to Port of Spain (POS)

An outdoor pool is featured at this vacation home, along with free WiFi in public areas and a terrace. A garden is also provided.

Hilton Trinidad & Conference Centre

per person

Sep 14 - Sep 20

found 24 hours 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.

The Chancellor Hotel

per person

Sep 14 - Sep 20

found 24 hours ago

Roundtrip flight included

New York (JFK) 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.

Top San Juan hotels deals

The Blue Mirage

Boundary Extension Road, San Juan, San Juan-Laventille Regional Corporation

$114 nightly

$125 total

Jul 14 - Jul 15

Total includes 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

25 GORBIN #1, San Juan, San Juan-Laventille Regional Corporation

$103 nightly

$112 total

Jul 6 - Jul 7

Total includes 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 "Dous" Modern Apartment

$138 nightly

$138 total

Jul 6 - Jul 7

Total includes taxes and fees

A hot tub is featured at this vacation home, along with laundry facilities.

Hot Tub

Kitchen

Hyatt Regency Trinidad

No 1 Wrighton Road, Port of Spain, Trinidad

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$260 total

Jul 27 - Jul 28

Total includes 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

Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG

No 1 Exposition Drive, Piarco, Trinidad

Free Cancellation

$169 nightly

$185 total

Aug 4 - Aug 5

Total includes 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

Radisson Hotel Trinidad

Wrightson Road, Port of Spain, Trinidad

Free Cancellation

$154 nightly

$168 total

Jul 12 - Jul 13

Total includes 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

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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 $550. 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.