Roosevelt Roads Vacation Packages

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    Save up to CA $1,096 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.
Sandy Beach Hotel

Sandy Beach Hotel

3 out of 5
Condado
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
6.2/10 (1,004 reviews)
Sandy Beach Hotel needs to update their website, pictures are not same as building structure and amenities are up to request and have to returned right after use other than that i guess it’s pretty good friendly staff.

Reviewed on Jul. 4, 2025

Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (429 reviews)
Great place to stay!! Very clean, safe & everything is in walking distance.

Reviewed on Jul. 29, 2025

Dorado Beach 5 Bedroom Villa

Dorado Beach 5 Bedroom Villa

3.5 out of 5
Higuillar
per person
Oct 21 - Oct 24
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to San Juan (SJU)
No reviews
Urbana Hotel

Urbana Hotel

2 out of 5
San Juan Antiguo
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (297 reviews)
Property was conveniently located. Easy to access tourist attractions from property. Staff were very friendly and helpful. We weren’t too happy about having to climb so many stairs due to our room being switched from 2nd to 3rd floor b/c our room door would not lock.

Reviewed on Jul. 28, 2025

Lazy Parrot Inn

Lazy Parrot Inn

3 out of 5
per person
Oct 1 - Oct 8
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (1,003 reviews)
Such amazing service!!! Amazing beautiful views!!!! Fell asleep to the sound of the coquis. Felt like we were in a tree house! It was so magical and unique. I highly recommend! Super family friendly! Great food and music!

Reviewed on Jul. 23, 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 $286 per night from Aug 24 to Aug 25
CA $286
CA $368 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (2,425 reviews)
"Had an amazing time!"

Reviewed on Jul. 29, 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 $479 per night from Aug 10 to Aug 11
CA $479
CA $649 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (2,109 reviews)
"friendly staff"

Reviewed on Jul. 28, 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
9/10 Wonderful! (3,111 reviews)
"Difficult to get reservations to eat at the resort. Bathrooms and bath tubs not handicapped friendly."

Reviewed on Jul. 28, 2025

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El Conquistador Resort
See all 2,116 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 $745. 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.