Roosevelt Roads Vacation Packages

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Top Roosevelt Roads Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lazy Parrot Inn

Lazy Parrot Inn

3 out of 5
Price was CA $1,389, price is now CA $727 per person
CA $727
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (1,001 reviews)
Limited food options, bed sheets stained

Reviewed on Aug. 19, 2025

Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Price was CA $2,263, price is now CA $845 per person
CA $845
per person
Sep 30 - Oct 6
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (453 reviews)
Is a small, but very comfortable hotel. The staff are very friendly and the breakfast is very good.

Reviewed on Aug. 20, 2025

Dorado Beach 5 Bedroom Villa

Dorado Beach 5 Bedroom Villa

3.5 out of 5
Higuillar
Price was CA $2,028, price is now CA $859 per person
CA $859
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to San Juan (SJU)
No reviews
San Agustin Apartments

San Agustin Apartments

3 out of 5
San Juan Antiguo
Price was CA $2,048, price is now CA $1,046 per person
CA $1,046
per person
Nov 8 - Nov 14
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (370 reviews)
Worked with me on short notice! Nice property! Great communication! Amazing hosts!

Reviewed on Aug. 16, 2025

Sandy Beach Hotel

Sandy Beach Hotel

3 out of 5
Condado
Price was CA $1,398, price is now CA $797 per person
CA $797
per person
Nov 10 - Nov 17
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
6.2/10 (1,004 reviews)
The property is centrally located

Reviewed on Aug. 19, 2025

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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 CA $357 per night from Sep 8 to Sep 9
CA $357
CA $460 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (2,509 reviews)
"I had a truly wonderful stay at this resort! From the moment I arrived, I felt safe, comfortable, and completely relaxed. The grounds were absolutely beautiful with palm trees and birds everywhere, creating such a peaceful and tropical atmosphere. The pools were huge, clean, and inviting. One of ..."

Reviewed on Aug. 19, 2025

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 CA $394 per night from Aug 29 to Aug 30
CA $394
CA $533 total
Aug 29 - Aug 30
includes taxes & fees
8.6/10 Excellent! (2,133 reviews)
"Beautiful! Very clean"

Reviewed on Aug. 18, 2025

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

El Conquistador Resort

4 out of 5
1000 Conquistador Avenue, Fajardo
Fully refundableReserve now, pay when you stay
The price is CA $347 per night from Aug 24 to Aug 25
CA $347
CA $476 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,160 reviews)
"We loved the overall setup. We stayed in the Brizas section, which is in need of renovation and, fortunately, scheduled for updates. Next time, we’ll most likely stay in the Vistas. The check-in process took far too long—about an hour and a half—which was definitely a drawback. One night, the fire ..."

Reviewed on Aug. 18, 2025

El Conquistador Resort
See all 2,076 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.
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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 $727. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.