San Juan Vacations from $538

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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.

The Latest San Juan 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 $683, price is now $538 per person
$538
per person
Nov 16 - Nov 20
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
8.8/10 Excellent! (74 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

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $1,155, price is now $838 per person
$838
per person
Nov 16 - Nov 20
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
9.2/10 Wonderful! (1,005 reviews)
I loved the ambiance, the service, the food, the scenery. Everything was outstanding. Last night our Server Kim told me about World of Hyatt. She went the extra mile, she signed me up so I could get points on the food I paid for. I've been there from Sep't 17, and no one told me anything about it.

Reviewed on Sep 23, 2025

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Price was $913, price is now $745 per person
$745
per person
Nov 16 - Nov 20
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
8/10 Very Good! (1,003 reviews)
Clean rooms , however one of the lights in the bathroom was not working and while we were asleep housekeeping came into the room. This was not acceptable. Other than that stay was great friendly staff.

Reviewed on Oct 4, 2025

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
Price was $837, price is now $692 per person
$692
per person
Nov 16 - Nov 20
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
7/10 Good! (30 reviews)
Overall. It was quiet and cozy.

Reviewed on Jul 13, 2025

Chaquacabana Resort & Beach Club

Chaquacabana Resort & Beach Club

3 out of 5
Price was $859, price is now $711 per person
$711
per person
Nov 16 - Nov 20
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
6/10 (82 reviews)
I was amazed at how beautifully designed this hotel was the rooms were gorgeous. Near the rooms are armed beautiful dark skinned men standing in front of a booth all night lol really makes you feel protected😜 the food and drinks were great as well as the views from the private beach

Reviewed on Sep 11, 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
$114 nightly
The price is $125 total per night from Oct 15 to Oct 16
$125 total
Oct 15 - Oct 16
Total with taxes and fees
10/10 Exceptional! (2 reviews)
"The property was beautiful. The room was comfortable and met every need. Enjoyed the pool and the quiet. The neighborhood did not seem safe, and there were no restaurants in close proximity, so a car is needed. Recommend for those not wanting to stay in Port of Spain. Host and staff were gracious ..."

Reviewed on Aug 1, 2025

The Blue Mirage
SherNest Guest House

SherNest Guest House

3 out of 5
25 GORBIN #1, San Juan, San Juan-Laventille Regional Corporation
$101 nightly
The price is $110 total per night from Oct 6 to Oct 7
$110 total
Oct 6 - Oct 7
Total with taxes and 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
Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
No 1 Wrighton Road, Port of Spain, Trinidad
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $239 total per night from Nov 2 to Nov 3
$239 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Great"

Reviewed on Sep 28, 2025

Hyatt Regency Trinidad
See all 386 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.

San Juan Essential Information

Language
English
Currency
Trinidad and Tobago dollars
Closest Airport
Piarco Intl. Airport (POS)
Max Temp Winter
80ºF
Max Temp Summer
85ºF
Top Sights
Maracas Beach, Las Cuevas Beach and Mohammed Ali Jinnah Memorial Mosque

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Frequently asked questions

How much does a San Juan vacation package cost?
You can snap up a vacation package to this destination from $538 on Expedia. However, how much your vacation to San Juan costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to San Juan?
November, December and January are the best times to search for cheap San Juan vacation packages. Opting to travel in quieter months means you can typically find better prices on hotels and flights.
How many days is enough for San Juan?
With a well-planned itinerary, you can easily visit the main San Juan attractions in a few days. But if you'd like to discover hidden gems or go on day tours, consider booking your San Juan vacation for longer.
How to find the best San Juan package deals?
Finding a cheap San Juan package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable San Juan package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a San Juan vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking accommodations and flights individually. Better still, you can personalize your San Juan escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to San Juan?
If you've got your San Juan vacation dates finalized, book as soon as you can to score some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for traveling on a whim.
How to plan a trip to San Juan?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to San Juan.
  2. Set a budget: Consider expenses like flights, food and transportation when working out how much to set aside for your trip to San Juan. Then, choose a hotel that matches your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Use our trip planning tool to discover San Juan: Research every aspect of your trip to San Juan with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide how long to go away for: Now that you're more familiar with San Juan, you can work out the right length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  5. Combine your accommodations and airfare: Once you've nailed down your travel dates and duration, book the ideal San Juan vacation package for you.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to see and do. Explore some of the exciting things to do in San Juan and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later San Juan vacation packages?
Your San Juan getaway should be an escape from your busy life, not a reason for money-related stress. So to give you that extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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Explore a world of travel with Expedia

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