Old San Juan Holidays

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Price found within the past 48 hours. Click for updated prices.
The Tryst Beachfront Hotel

The Tryst Beachfront Hotel

3.5 out of 5
Condado
Price was €1,745, price is now €1,276 per person
€1,276
per person
14 Apr - 21 Apr
just found
Return direct flight included
Dublin (DUB) to San Juan (SJU)
8.2/10 Very Good! (581 reviews)
I stayed for 6 nights at The Tryst Hotel in San Juan, Puerto Rico, and once again it did not disappoint. The rooms were clean and neat, just like last year, which I really appreciate. It’s always great coming back to a place that keeps its standards high. The staff was amazing — very helpful, professional, and polite throughout our entire stay. They truly make you feel welcome and taken care of. The hotel is very gay-friendly, and you can absolutely feel that comfortable, relaxed vibe. It’s a great place for gay travelers who want to feel at home while enjoying San Juan. I would definitely stay here again!

Reviewed on 23 Feb 2026

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was €2,681, price is now €1,621 per person
€1,621
per person
14 Apr - 21 Apr
just found
Return direct flight included
Dublin (DUB) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
Nice little boutique hotel in a great spot however, the staff is really hit and miss and the place is in need of a touch up here and there for sure.

Reviewed on 25 Feb 2026

Old San Juan Rentals

Old San Juan Rentals

3.5 out of 5
Old San Juan
Save 100% on your flight
Price was €2,773, price is now €1,832 per person
€1,832
per person
14 Apr - 21 Apr
just found
Return direct flight included
Dublin (DUB) to San Juan (SJU)
8.6/10 Excellent! (667 reviews)
Charming, clean great location and helpful staff.

Reviewed on 20 Feb 2026

Don Rafa Boutique Hotel & Residences

Don Rafa Boutique Hotel & Residences

4 out of 5
Santurce
Save 100% on your flight
Price was €4,464, price is now €3,128 per person
€3,128
per person
14 Apr - 21 Apr
just found
Return direct flight included
Dublin (DUB) to San Juan (SJU)
9.4/10 Exceptional! (334 reviews)
What a friendly attentive staff. Room is very clean and big

Reviewed on 26 Feb 2026

Picuas Village

Picuas Village

3 out of 5
Zarzal
Price was €1,980, price is now €1,456 per person
€1,456
per person
14 Apr - 21 Apr
just found
Return direct flight included
Dublin (DUB) to San Juan (SJU)
7.4/10 Good! (58 reviews)
Good location, quite and ocean front

Reviewed on 27 Jun 2025

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
Isla Verde featuring sailing, a sandy beach and boating

Isla Verde

1 out of top 10 points of interest in this area
4/5(2 area reviews)

White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico.

Find hotels in Isla Verde

Top hotels in Old San Juan

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 €254 per night from 16 Mar to 17 Mar
€254
16 Mar - 17 Mar
includes taxes & fees
9/10 Wonderful! (1,538 reviews)
First the car I booked with you never showed up so you owe me a refund for that. Had to pay a taxi 45.00 to take us to the hotel and never got our room until 6:00 pm. I tried to call you, and gave up after being on hold for over a half an hour.

Reviewed on 26 Feb 2026

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 €163 per night from 3 Mar to 4 Mar
€163
3 Mar - 4 Mar
includes taxes & fees
9/10 Wonderful! (509 reviews)
Bed was very comfortable. Staff was friendly and helpful. Location was perfect for us

Reviewed on 25 Feb 2026

Armas Hotel
El Colonial - Adults Only

El Colonial - Adults Only

3.5 out of 5
312 C. de San Francisco San Juan San Juan
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,489 reviews)
Great staff, clean room

Reviewed on 26 Feb 2026

Get rates
El Colonial - Adults Only
See all 3,781 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 €1,276, 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.

Popular places to visit

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

Castillo San Felipe del Morro

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
La Fortaleza as well as a couple

La Fortaleza

The official residence of the governor of Puerto Rico is a vast mansion and fortress that is open to the public on guided tours.

La Fortaleza
Plaza de Armas

Plaza de Armas

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.

Plaza de Armas

Things to do

FlyDining: Sunset & City Lights Dinner Over Old San Juan

FlyDining: Sunset & City Lights Dinner Over Old San Juan

€134
per adult
92% of travellers recommend
FlyDining: Sunset & City Lights Dinner Over Old San Juan
San Juan: Old San Juan Sunset Cruise with Drinks & Transfer

San Juan: Old San Juan Sunset Cruise with Drinks & Transfer

€83
per adult
92% of travellers recommend
San Juan: Old San Juan Sunset Cruise with Drinks & Transfer
San Juan: Casa Bacardi Distillery Tour

San Juan: Casa Bacardi Distillery Tour

€75
per adult
92% of travellers recommend
San Juan: Casa Bacardi Distillery Tour
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.