Obrero Holidays from AU$1,280

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Your Obrero Holiday

Your next big journey is just around the corner with a holiday package to Obrero. Fun, food and nonstop great times — you're bound to find it in this neighbourhood. Start your trip to Obrero by checking out nearby attractions such as Jose Miguel Agrelot Coliseum, Hiram Bithorn Stadium and Condado Beach. Don't just dream it — make it happen! Secure your ultimate Obrero holiday with Expedia and travel your way.

Top Holiday Package Deals in Obrero

Price found within the past 48 hours. Click for updated prices.
Casa Wilson Inn

Casa Wilson Inn

3.5 out of 5
Condado
Save 100% on your flight
per person
6 Nov - 13 Nov
found 19 hours ago
Return flight included
New York (NYC) to San Juan (SJU)
9/10 Wonderful! (689 reviews)
Friendly and courteous staff

Reviewed on 25 Jul. 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4 out of 5
Condado
Save 100% on your flight
per person
6 Nov - 13 Nov
found 19 hours ago
Return flight included
New York (NYC) to San Juan (SJU)
8.8/10 Excellent! (522 reviews)
I like how the hotel is set up its is very romantic and couples friendly. The front desk staff was very helpful and friendly. My one complaint is that the bell boys did not do their job at all, I can count on my hand the number of times the door was opened for me and my wife with 4 guys standing outside on their phones. I was a vip customer but did not recieve that treatment at all times.

Reviewed on 7 Aug. 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
per person
6 Nov - 13 Nov
found 19 hours ago
Return flight included
New York (NYC) to San Juan (SJU)
9.2/10 Wonderful! (230 reviews)
Property is nice and it on the beach and have access to umbrella and chair. The pool needs remodel. The rooftop restaurant delicious and the staff was great. Only issue was with the personal car service I paid for pickup at the airport, took a taxi to the hotel.

Reviewed on 9 Aug. 2025

Bali Posh Hotel PR

Bali Posh Hotel PR

2.5 out of 5
Isla Verde
Save 100% on your flight
per person
6 Nov - 13 Nov
found 19 hours ago
Return flight included
New York (NYC) to San Juan (SJU)
8.6/10 Excellent! (680 reviews)
Great, boutique hotel nestled in isla verde. Clean, quiet and attentive personal.

Reviewed on 13 Aug. 2025

Trópica Beach Hotel

Trópica Beach Hotel

3.5 out of 5
Santurce
Save 100% on your flight
per person
6 Nov - 13 Nov
found 19 hours ago
Return flight included
New York (NYC) to San Juan (SJU)
9.4/10 Exceptional! (819 reviews)
Property looked chic but I didn't stay long enough to give a detailed review. Bed was comfortable, ac worked too well, and staff was amazing.

Reviewed on 31 Jul. 2025

Our guide on where to stay in Obrero

Find the best Obrero areas and neighborhoods for the activities you enjoy most. Learn more about Obrero
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 Obrero Hotel Deals

Caribe Hilton

Caribe Hilton

4.5 out of 5
1 San Geronimo Street, San Juan
Fully refundableReserve now, pay when you stay
The price is AU$370 per night from 26 Aug to 27 Aug
AU$370
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (2,132 reviews)
"Everything was beautiful and comfortable"

Reviewed on 12 Aug. 2025

Caribe Hilton
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

4 out of 5
200 Coco Beach Blvd. Highway 955-I, Río Grande
Fully refundableReserve now, pay when you stay
The price is AU$509 per night from 2 Sept to 3 Sept
AU$509
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (2,476 reviews)
"Was an amazing experience, love the hotel staff and all the areas"

Reviewed on 14 Aug. 2025

Hyatt Regency Grand Reserve Puerto Rico
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
6063 Isla Verde Avenue, Carolina
Fully refundableReserve now, pay when you stay
The price is AU$716 per night from 17 Aug to 18 Aug
AU$716
17 Aug - 18 Aug
includes taxes & fees
8.4/10 Very Good! (1,890 reviews)
"We enjoyed our stay"

Reviewed on 12 Aug. 2025

Fairmont El San Juan Hotel
See all 3,693 properties in Obrero
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.
All Inclusive Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Obrero holiday package cost?
From as little as AU$1,280. Yes, you read that correctly. Our Obrero holiday packages are the quickest way to stretch your budget further. Combine your hotels, flights and rental car and explore this lively destination.
How do I get a cheap travel package to Obrero?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into an Obrero holiday package and save. Score even more bargains when you add extras such as experiences or tours to your booking. But that's not the only good part. You have the freedom to customize your holiday your own way. We offer over 550 airlines and 1 000 000 hotels throughout the world, so that everyone has a chance to travel and live out those holiday fantasies.
Where should I stay in Obrero?
Make sightseeing a breeze by staying someplace close to Obrero's big attractions. Luquillo Beach and Puerto Rico Convention Centre are two of the best in the area.
How far in advance should I book my Obrero holiday?
It's hard to pick the ideal time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available up to a year in advance. If you're booking last minute, fear not. Budget prices appear from time to time just weeks before departure dates.
What does an Expedia Obrero travel package include?
Travel packages include rental cars, flights and hotels, but you can mix and match them to create your dream Obrero holiday. You can also add on fun things like activities and tours once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking an Obrero travel package?
A travel package can be easier on the credit card than separately booking everything you need for your getaway. For example, bundle your hotels, flights and rental cars and save big. Whatever your holiday goals are, you're bound to find a package within your budget.
Can I choose my airline with an Obrero Expedia holiday package?
Yes, the choice is all yours. We have access to over 550 partner airlines all over the world, so you can tailor your Obrero escape according to your needs and budget.
If I'm not able to travel, can I cancel my Obrero holiday package?
Your situation can change in a flash, so yes. You may be able to change or cancel your Obrero holiday package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make changes, but your car rental company, airline or hotel may charge a fee. Looking for more information? Have a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Obrero

Port of San Juan

Port of San Juan

Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art galleries.

Port of San Juan
Luquillo Beach featuring a sandy beach

Luquillo Beach

Sample local street food or doze under a palm tree on this picturesque stretch of coast.

Luquillo Beach
Condado Beach which includes kayaking or canoeing, tropical scenes and a beach

Condado Beach

This beach within the bustling city of San Juan is the perfect place to relax for a few hours.

Condado Beach

Activities

El Yunque Rainforest Natural Waterslide on a sunny Puerto Rico Day

El Yunque Waterslide and Waterfall Tour with Food and Photos

AU$105
per adult
94% of travellers recommend
El Yunque Waterslide and Waterfall Tour with Food and Photos
Puerto Rico: UTV and Can-Am Sightseeing Tours

Puerto Rico: UTV and Can-Am Sightseeing Tours

AU$104
per adult
74% of travellers recommend
Puerto Rico: UTV and Can-Am Sightseeing Tours
City Lights / GLOW

LED Kayak Night Glow Tour in Condado Lagoon

AU$114
per adult
92% of travellers recommend
LED Kayak Night Glow Tour in Condado Lagoon
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.