Old San Juan Vacation Packages
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Top Holiday Package Deals in Old San Juan
Price found within the past 48 hours. Click for updated prices.
WALD HAUS by DW
CA $3,839
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (11 reviews)
The home itself is absolutely stunning but the road to the villa is not just narrow, it's washed out in many places, we struggled to navigate the potholes even with a jeep and an SUV, I would not drive it at night. There are great amenities like the fridge and bathroom downstairs, the coffee / cocktail bar is fabulous.The kitchen was well-stocked with basic spices and supplies but it was crawling with roaches. Wifi is spotty so be sure to have the guidebook downloaded and screenshots of the phone number to call because the phone number posted throughout the villa is not functioning. Even in August the combination of ACs, fans, and breezes kept the temprature very comfortable. Excellent pool, though very little shallow area, if you're traveling with kids or weaker swimmers.
Reviewed on Aug 13, 2026
Ola Boutique Hotel
Condado
CA $1,302
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (957 reviews)
The staff is amazing. I enjoyed myself here and will definitely book this hotel again.
Reviewed on Sep 20, 2026
Where to stay in Old San Juan
Find the best Old San Juan areas and neighborhoods for the activities you enjoy most. Learn more about Old San Juan
Condado
1 out of top 10 points of interest in this area
Oceanfront and upscale, Condado boasts picturesque beaches alongside hotels, nightclubs, casinos, and shops. Stroll through La Ventana al Mar park, and enjoy easy access to public transport via T21 and D53 bus routes.
Isla Verde
1 out of top 10 points of interest in this area
White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico.
Santurce
3 out of top 10 points of interest in this area
Bask in the sun on Atlantic Ocean beaches and experience vibrant nightlife at La Placita de Santurce, while exploring museums like the Museum of Art of Puerto Rico. Enjoy easy access to public transportation via bus lines and the Tren Urbano.
Ocean Park
Upscale beachfront community with trendy beachgoers, Ocean Park offers kitesurfing and windsurfing opportunities. Stroll along Calle Loíza for bars, restaurants, and boutiques or unwind at nearby Parque Barbosa.
San Juan Antiguo
1 out of top 10 points of interest in this area
Walk down picturesque cobbled streets lined with centuries old buildings and some of the most popular historical attractions in Puerto Rico.
Old San Juan Hotel Deals
Hotel Rumbao, a Tribute Portfolio Hotel
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
CA $205
CA $287 total
Sep 28 - Sep 29
includes taxes & fees
Armas Hotel
202 C. San José San Juan San Juan
Fully refundableReserve now, pay when you stay
CA $97
CA $144 total
Sep 28 - Sep 29
includes taxes & fees
EL Colonial Hotel Open Bar Adults Only
312 C. de San Francisco San Juan San Juan
Fully refundableReserve now, pay when you stay
CA $126
CA $167 total
Sep 22 - Sep 23
includes taxes & fees
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 does an Old San Juan vacation package cost?
Maybe less than you imagined — from just CA $894, actually! By bundling hotels, flights and car rentals into your own custom-made vacation package, your trip to Old San Juan is just clicks away.
How do I get a cheap travel package to Old San Juan?
Creating your own Old San Juan vacation package with Expedia is an easy way to save. We have over 550 airlines and 1,000,000 hotels throughout the world. With such an amazing range to pick from, you'll have no worries creating your ideal vacation.
Where should I stay in Old San Juan?
Take the leg work out of sightseeing by staying in a hotel close to Old San Juan's terrific attractions. San Juan Gate and Catedral Basilica Menor de San Juan Bautista are two of the most popular.
What are the top hotels in Old San Juan?
Secure a room at Palacio Provincial - Adults Only. It's one of this neighborhood's most sought-after properties. Another highly rated option in Old San Juan is El Colonial - Adults Only.
How far in advance should I book my Old San Juan vacation?
Get rewarded with the biggest variety and the cheapest prices by booking your Old San Juan adventure nice and early. Airlines typically advertise flights around a year before departure, so reserve your spot ASAP. That said, Expedia is committed to providing you with the best bargains around, so it's never a bad time to book your dream vacation!
What does an Expedia Old San Juan travel package include?
Expedia has everything you need to arrange your Old San Juan trip, but how your package is structured is totally up to you. Pick from a combination of rental cars, flights and hotels. Looking for some experiences or tours to keep you entertained? Once you've made your booking, you can add them on too. No matter your style or budget, there's a package deal to match your needs.
What should I know before booking an Old San Juan travel package?
A travel package can be tailored to your budget and is a fantastic way to make your budget go further. How much you include is your call. Rental cars, hotels and flights — decide on a combination that suits your style.
If I'm not able to travel, can I cancel my Old San Juan vacation package?
You can. We understand that even the best-laid plans can fail, so we're here to help if you need to make changes to your Old San Juan vacation package. You may be able to cancel or change your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
Stay near popular Old San Juan attractions
San Juan Gate
9.0/10 (4,255 reviews)
Enter San Juan through the last remaining gateway from the city’s walls and discover the military history of its atmospheric Old Town.
Castillo San Felipe del Morro
9.6/10 (1,834 reviews)
This walled fortress was once used to protect Puerto Rico from invading colonies, and today offers visitors a dramatic reminder of that history.
Photo by Raquel Chin Wo Astua
Puerta de San Juan
Learn about the local history of San Juan when you spend time at Puerta de San Juan. Experience the area's acclaimed art scene and fascinating museums.
La Fortaleza
9.2/10 (1,318 reviews)
The official residence of the governor of Puerto Rico is a vast mansion and fortress that is open to the public on guided tours.
Castillo de San Cristobal
9.4/10 (1,486 reviews)
Marvel at a Spanish fortification on the edge of Old San Juan, a place full of haunting myths, fascinating history and stunning photography spots.
Catedral Basilica Menor de San Juan Bautista
9.0/10 (2,906 reviews)
Discover the curious relics and gorgeous stained-glass windows of Old San Juan’s religious treasure, a 16th-century cathedral with a colorful history.
Plaza de Armas
9.0/10 (330 reviews)
San Juan’s hub of civic life is also one of the most popular social destinations, where locals come to drink coffee and trade stories.
Paseo de la Princesa
9.8/10 (13 reviews)
During your trip to San Juan, you can do some window-shopping at Paseo de la Princesa. Experience the area's fascinating museums and acclaimed art scene.
Things to do
El Yunque Rainforest Guided Hiking Tour
CA $122
per traveller
96% of travellers recommend
San Juan: Casa Bacardi Distillery Tour
CA $123
per adult
94% of travellers recommend
Puerto Rico: The Beast Zipline at Toro Verde Adventure Park
CA $93
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.