San Juan Vacation Packages

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Your San Juan Vacation

With everything planned before you go away, our San Juan vacation packages mean you can focus more on having fun. No matter if you're based in the neighborhood of Downtown Port of Spain, which is great for culture, or somewhere else, this city promises an array of discoveries. If your trip to San Juan includes a little sightseeing, check out popular attractions like Queens Park Savanah, Ariapita Avenue and Movietowne. Your San Juan vacation is clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored to suit your travel style.

Top San Juan Vacation Deals

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
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
8.8/10 Excellent! (70 reviews)
The property is gated, clean and secure. The rooms are well appointed, and supported by polite and personal support staff. There is also 24/7 security surveillance.

Reviewed on Jul. 3, 2025

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
8/10 Very Good! (1,003 reviews)
I loved the pool area, and the balconies have Beautiful views.

Reviewed on Jul. 24, 2025

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
7/10 Good! (29 reviews)
Overall. It was quiet and cozy.

Reviewed on Jul. 13, 2025

Cara Hotels Trinidad

Cara Hotels Trinidad

3 out of 5
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
7.8/10 Good! (215 reviews)
The staff were sympathetic and friendly. The pool area and deck are nice. The view is gorgeous 😍😍. I would give an average rating as I believe the rooms can do with some upgrades. Otherwise can be an ideal stay for families who want to take a vacation away from home.😃

Reviewed on Jul. 3, 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Port of Spain (POS)
9.2/10 Wonderful! (1,011 reviews)
Staff were friendly. The cleanliness. However, the prices for food and services were exuberantly overinflated. Staff’s lack of clarity of ingredients in meals. For example, I was served a meal with milk when asked for confirmation that it was a vegan meal. One staff told the definition of vegan is no rice, no bread. Extremely limited activities/entertainment.

Reviewed on Jul. 27, 2025

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San Juan Hotel Deals

The Blue Mirage

The Blue Mirage

2 out of 5
Boundary Extension Road, San Juan, San Juan-Laventille Regional Corporation
The price is CA $140 per night from Jul 29 to Jul 30
CA $140
CA $170 total
Jul 29 - Jul 30
includes taxes & fees
10/10 Exceptional! (1 review)
"Great location and lovely place. Very clean and quiet. I had a really great time staying here."

Reviewed on May 19, 2025

The Blue Mirage
SherNest Guest House

SherNest Guest House

3 out of 5
25 GORBIN #1, San Juan, San Juan-Laventille Regional Corporation
The price is CA $125 per night from Jul 29 to Jul 30
CA $125
CA $151 total
Jul 29 - Jul 30
includes taxes & fees
10/10 Exceptional! (2 reviews)
"The property is in the heart of San Juan, but the gps location is not accurate. We were able to call the owner who gave us actual directions to the property. Once we got there, everything improved. The owner contacted you in advance to confirm your stay, so that was nice. I had previously booked ..."

Reviewed on Apr. 5, 2025

SherNest Guest House
The Bey

The Bey

3 out of 5
43 Jogie Rd, San Juan, San Juan-Laventille Regional Corporation
"The owner was very nice and accommodating. I felt comfortable and at home. Would definitely recommend to anyone."

Reviewed on Jul. 30, 2022

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The Bey
See all 385 properties in San Juan
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.
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Frequently asked questions

How much does a San Juan vacation package cost?
Offering great value package deals from CA $874 on Expedia, you'll be pleasantly surprised at how much a vacation to San Juan costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to San Juan?
To pick up cheap San Juan vacation packages, plan your getaway outside of peak times such as school holidays. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for San Juan?
Typically, a handful of days is enough to visit the major sights during your San Juan vacation. But if you'd like to have more time to relax or go on day tours, consider extending your itinerary.
How to find the best San Juan package deals?
Finding a cheap San Juan package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical San Juan package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a San Juan vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still have the flexibility to create a customized San Juan vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to San Juan?
If you're planning a spontaneous San Juan trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to San Juan?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit San Juan.
  2. Budget wisely: On top of the cost of your accommodations, you should consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that could crop up during your trip to San Juan.
  3. Decide your trip length: Think about how much time you want to spend discovering San Juan. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the ideal San Juan vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.