Roosevelt Roads Vacation Packages
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Roosevelt Roads Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Hotel
Isla Verde
CA $3,372
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to San Juan (SJU)
8.6/10 Excellent! (2,233 reviews)
The property was ok but the rooms were sub par. Freezing and you couldn’t turn the temp up or down. Food was mediocre for way too much money.
Reviewed on Oct 12, 2026
WALD HAUS by DW
CA $3,086
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Ready to book your vacation to Roosevelt Roads?
Roosevelt Roads Hotel Deals
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
CA $375
CA $482 total
Oct 25 - Oct 26
includes taxes & fees
El Conquistador Resort
1000 Conquistador Avenue Fajardo
Fully refundableReserve now, pay when you stay
CA $422
CA $561 total
Oct 13 - Oct 14
includes taxes & fees
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
CA $438
CA $602 total
Oct 18 - Oct 19
includes taxes & fees
8.8/10 Excellent! (2,264 reviews)
"Having only one working elevator in a sold out upscale resort is unacceptable. Also pricing that was advertised didn’t translate at the resort was hit with additional charges at the shows onsite. Also had issues with resort credits the property is stunning expect to pay astronomical prices for food ..."
Reviewed on Oct 12, 2026
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.
Stay near popular Roosevelt Roads attractions
Playa Blanca
6.6/10 (4 reviews)
Why not spend a lazy afternoon at Playa Blanca during your trip to Guayacán?
Frequently asked questions
How much does a Roosevelt Roads vacation package cost?
Be ready to book, because a getaway to Roosevelt Roads starts from an affordable CA $983. 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 vacation 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 vacation with the whole family or traveling with someone special, organizing a trip to Roosevelt Roads is better with a package.
What are the top hotels in Roosevelt Roads?
People traveling to Roosevelt Roads often book Vistaazulpenthouse or Cbrava Apartment With Ocean View/ Pool. You'll find them in Machos. Another interesting neighborhood 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 vacation?
Savvy travelers 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 vacation 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 vacation 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 vacation rentals like oceanfront condos and short-term homes. You've got loads of choices!
Can I choose my airline with a Roosevelt Roads Expedia vacation 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 vacation 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 vacation 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.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
