Roosevelt Roads Holidays from AU$985

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The Latest Roosevelt Roads Holiday Deals

Price found within the past 48 hours. Click for updated prices.
El Colonial - Adults Only

El Colonial - Adults Only

3.5 out of 5
Old San Juan
Price was AU$1,342, price is now AU$985 per person
AU$985
per person
27 Sept - 1 Oct
found 1 day ago
Return direct flight included
San Diego (SAN) to San Juan (SJU)
9.4/10 Exceptional! (1,301 reviews)
Staff was great, the shower was bad the mixer did not work. Water temp kept varying badly.

Reviewed on 27 Aug. 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4 out of 5
Condado
Save 100% on your flight
Price was AU$2,044, price is now AU$1,321 per person
AU$1,321
per person
27 Sept - 1 Oct
found 1 day ago
Return direct flight included
San Diego (SAN) to San Juan (SJU)
8.6/10 Excellent! (528 reviews)
was very convinient, close to a lot of restaurant.

Reviewed on 25 Aug. 2025

Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
San Juan Antiguo
Save 100% on your flight
Price was AU$1,584, price is now AU$1,063 per person
AU$1,063
per person
27 Sept - 1 Oct
found 1 day ago
Return direct flight included
San Diego (SAN) to San Juan (SJU)
9/10 Wonderful! (467 reviews)
Great spot close to port . Rooms are well kept and clean . Staff was very helpful

Reviewed on 26 Aug. 2025

Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
Isla Verde
Save 100% on your flight
Price was AU$1,900, price is now AU$1,294 per person
AU$1,294
per person
27 Sept - 1 Oct
found 1 day ago
Return direct flight included
San Diego (SAN) to San Juan (SJU)
8.4/10 Very Good! (1,920 reviews)
I Love the fact that you can park there in the hotel. Also is easy to walk to Pharmacies and restaurants.

Reviewed on 25 Aug. 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was AU$1,968, price is now AU$1,354 per person
AU$1,354
per person
27 Sept - 1 Oct
found 1 day ago
Return direct flight included
San Diego (SAN) to San Juan (SJU)
9/10 Wonderful! (243 reviews)
i enjoyed it the only thing is that there was construction during the day but it doesn’t really matter since no one’s sitting in the hotel all day anyway. but we had a great time and the restaurant was great staff was nice

Reviewed on 26 Aug. 2025

Roosevelt Roads Holiday

Roosevelt Roads Essential Information

Language
Spanish
Currency
U.S dollars
Local Welcome
¡Hola!
Local Goodbye
Adiós
Closest Airport
Luis Munoz Marin Intl. Airport (SJU)
Top Sights
Playa Blanca, Playa Los Machos and Playa Medio Mundo

Our pick of the best Roosevelt Roads Hotel Deals

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$512 per night from 4 Sept to 5 Sept
AU$512
4 Sept - 5 Sept
includes taxes & fees
Hyatt Regency Grand Reserve Puerto Rico
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

5 out of 5
6000 Rio Mar Boulevard, Río Grande
Fully refundableReserve now, pay when you stay
The price is AU$622 per night from 30 Aug to 31 Aug
AU$622
30 Aug - 31 Aug
includes taxes & fees
8.4/10 Very Good! (2,143 reviews)
"The most beautiful place to stay especially if you plan on doing activities in the rainforest! 10/10 experience!"

Reviewed on 23 Aug. 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
El Conquistador Resort

El Conquistador Resort

4 out of 5
1000 Conquistador Avenue, Fajardo
9/10 Wonderful! (3,167 reviews)
"Excellent place our room had no hot water though"

Reviewed on 25 Aug. 2025

Get rates
El Conquistador Resort
See all 2,082 properties in Roosevelt Roads
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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All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Roosevelt Roads holiday package cost?
Be ready to book, because a getaway to Roosevelt Roads starts from an affordable AU$985. When you bundle your flights, hotels and car rentals into a package, you'll pick up the biggest bargains.
How do I get a cheap travel package to Roosevelt Roads?
Imagine all the wonderful things you could do in Roosevelt Roads with a wad of extra cash in your wallet. Watch your savings stack up when you combine your flights and hotel into a Roosevelt Roads holiday package. You have loads of choice when it comes to booking with Expedia too. In fact, you can pick from over 550 airlines and 1 000 000 hotel options throughout the world. Whether you're taking a holiday with the whole family or travelling with someone special, organising a trip to Roosevelt Roads is better with a package.
What are the top hotels in Roosevelt Roads?
People travelling to Roosevelt Roads often book Vistaazulpenthouse or Cbrava Apartment With Ocean View/ Pool. You'll find them in Machos. Another interesting neighbourhood is Guayacán. Exclusive Villas, Hidden Paradise Near Beaches and Escape Half The World are well-liked options in this part of town.
How far in advance should I book my Roosevelt Roads holiday?
Savvy travellers often book early. You can generally compare international airfares on Expedia up to a year before your intended flight. If you're late to book, there's no need to worry. Discounted prices occasionally occur just weeks before departure.
What does an Expedia Roosevelt Roads travel package include?
It all comes down to what type of trip you're thinking about. Roosevelt Roads holiday deals can include hotels, car rentals and flights. You can mix and match to find the travel package that suits you. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Roosevelt Roads travel package?
Locking in all the parts of your holiday together is a simple way to save. Combine your airfares, rental cars and hotels into a tidy little package. But hotels aren't your only option. Expedia has all kinds of properties, including holiday homes like oceanfront condos and short-term homes. You've got loads of choices!
Can I choose my airline with a Roosevelt Roads Expedia holiday package?
Yes, so take your pick! Expedia has access to more than 550 airlines throughout the world, so you can customize your Roosevelt Roads adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Roosevelt Roads holiday package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can change or cancel your Roosevelt Roads holiday package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.