Old San Juan Holidays from NZ$1,804

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Top Holiday Package Deals in Old San Juan

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

Romeo Gay Hotel

4 out of 5
San Juan Antiguo
Price was NZ$2,634, price is now NZ$1,804 per person
NZ$1,804
per person
16 Mar - 22 Mar
found 17 hours ago
Return flight included
Chicago (ORD) to San Juan (SJU)
9/10 Wonderful! (121 reviews)
Room was clean. Staff were very kind and helpful

Reviewed on 28 Dec 2025

Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Save 100% on your flight
Price was NZ$3,800, price is now NZ$2,135 per person
NZ$2,135
per person
16 Mar - 22 Mar
found 17 hours ago
Return flight included
Chicago (ORD) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
There was no spa. No hair dryer, frig, safe in the room. I would recommend upgrading to a larger room if you are part of a couple.

Reviewed on 27 Dec 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Condado
Save 100% on your flight
Price was NZ$4,994, price is now NZ$2,949 per person
NZ$2,949
per person
16 Mar - 22 Mar
found 17 hours ago
Return flight included
Chicago (ORD) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
This place is beautiful a must stay

Reviewed on 25 Dec 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was NZ$4,887, price is now NZ$2,915 per person
NZ$2,915
per person
16 Mar - 22 Mar
found 17 hours ago
Return flight included
Chicago (ORD) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
Special thanks for amazing Staff all of them are amazing ,reception and guys was opening the doors each time you going out or entering. The best location everything close shops, restaurants ,pharmacy. Has 2 pools.The beach right infront of hotel.The towels, umbrellas are included. Even they help you to put towels. This hotel supposed to be 5* Vikky was nice on reception other girls too just don't remember the names.10/10 .Thank you.

Reviewed on 24 Dec 2025

The Oliver Hotel

The Oliver Hotel

3 out of 5
San Juan Antiguo
Save 100% on your flight
Price was NZ$2,908, price is now NZ$1,851 per person
NZ$1,851
per person
16 Mar - 22 Mar
found 17 hours ago
Return flight included
Chicago (ORD) to San Juan (SJU)
9/10 Wonderful! (50 reviews)
I truly enjoyed my stay at the Oliver Hotel. I arrived early in the morning and was pleasantly surprised that my room was already ready for check-in. Everything was clean, well-kept, and beautiful. The location is fantastic, just a 15-minute walk to Old San Juan and the beach.

Reviewed on 27 Dec 2025

Our guide on 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

Condado

1 out of top 10 points of interest in this area

Experience San Juan at its most modern in a chic neighborhood packed with high-end fashion shops, elegant casinos and popular restaurants.

Find hotels in Condado

Our pick of the best Old San Juan Hotel Deals

Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

4 out of 5
100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
The price is NZ$467 per night from 12 Jan to 13 Jan
NZ$467
12 Jan - 13 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,412 reviews)
everything is great!

Reviewed on 26 Dec 2025

Hotel Rumbao, a Tribute Portfolio Hotel
Armas Hotel

Armas Hotel

2 out of 5
202 C. San José San Juan San Juan
Fully refundableReserve now, pay when you stay
The price is NZ$391 per night from 21 Jan to 22 Jan
NZ$391
21 Jan - 22 Jan 2026
includes taxes & fees
9/10 Wonderful! (390 reviews)
Clean room

Reviewed on 24 Dec 2025

Armas Hotel
Alma San Juan

Alma San Juan

4 out of 5
405 C. de San Francisco San Juan San Juan
Fully refundableReserve now, pay when you stay
The price is NZ$450 per night from 12 Jan to 13 Jan
NZ$450
12 Jan - 13 Jan 2026
includes taxes & fees
9/10 Wonderful! (332 reviews)
Centrally located in the city of old San Juan...great restaurants and shops...historic places

Reviewed on 22 Dec 2025

Alma San Juan
See all 3,789 properties in Old 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.

Frequently asked questions

How much does an Old San Juan holiday package cost?
Maybe less than you imagined — from just NZ$1,804, actually! By bundling hotels, flights and car rentals into your own custom-made holiday 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 holiday 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 holiday.
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 neighbourhood'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 holiday?
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 holiday!
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.
Can I choose my airline with an Old San Juan Expedia holiday package?
Expedia offers access to more than 550 airline partners globally, so you certainly can. Just pick the carrier you want and create your ideal Old San Juan trip.
If I'm not able to travel, can I cancel my Old San Juan holiday 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 holiday 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.

Discover the most popular places to visit in Old San Juan

Castillo San Felipe del Morro showing general coastal views and heritage elements

Castillo San Felipe del Morro

4/5(2 reviews)

This walled fortress was once used to protect Puerto Rico from invading colonies, and today offers visitors a dramatic reminder of that history.

Castillo San Felipe del Morro

Activities

El Yunque Rainforest Natural Waterslide on a sunny Puerto Rico Day

El Yunque Waterslide and Waterfall Tour with Food and Photos

NZ$92
per adult
96% of travellers recommend
El Yunque Waterslide and Waterfall Tour with Food and Photos
Small-Group El Yunque Waterslide Adventure & transportation

Small-Group El Yunque Waterslide Adventure & transportation

NZ$62
per adult
98% of travellers recommend
Small-Group El Yunque Waterslide Adventure & transportation
Single female snorkeler in the ocean off the coast of Puerto Rico

Catamaran Sail & Snorkeling in the Caribbean with Lunch

NZ$317
per traveller
92% of travellers recommend
Catamaran Sail & Snorkeling in the Caribbean with Lunch
See all activities in San Juan
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.