Roosevelt Roads Vacation Packages

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    Save 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.
Serena Boutique Hotel

Serena Boutique Hotel

3.5 out of 5
Price was CA $1,937, price is now CA $1,280 per person
CA $1,280
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.4/10 Exceptional! (297 reviews)
Hospitalidad

Reviewed on Nov 6, 2026

Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
Puerta de Tierra
Save 100% on your flight
Price was CA $2,906, price is now CA $1,730 per person
CA $1,730
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.8/10 Excellent! (755 reviews)
I like the place very clean

Reviewed on Nov 5, 2026

Villa Gaviota with private pool by Otium

Villa Gaviota with private pool by Otium

3 out of 5
Zarzal
Price was CA $4,240, price is now CA $2,551 per person
CA $2,551
per person
Jan 16 - Jan 23
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
No reviews

SELVA by DW

SELVA by DW

4 out of 5
Pitahaya
Save 100% on your flight
Price was CA $7,950, price is now CA $5,031 per person
CA $5,031
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
10/10 Exceptional! (3 reviews)
Todo estuvo perfecto limpieza 💯communication al 💯 y los servicios ofrecido todo me parecio exelente buen olor en las toallas y sabanas ,

Reviewed on Jun 25, 2026

Condado Lagoon by Otium

Condado Lagoon by Otium

3 out of 5
Puerta de Tierra
Price was CA $3,751, price is now CA $2,475 per person
CA $2,475
per person
Dec 9 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
7.6/10 Good! (59 reviews)
As described. Central location .

Reviewed on Nov 5, 2026

Ready to book your vacation to Roosevelt Roads?

 

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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 $369 per night from Nov 10 to Nov 11
CA $369
CA $475 total
Nov 10 - Nov 11
includes taxes & fees
Hyatt Regency Grand Reserve Puerto Rico
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 $466 per night from Nov 8 to Nov 9
CA $466
CA $607 total
Nov 8 - Nov 9
includes taxes & fees
9.2/10 Wonderful! (3,686 reviews)
"Water park"

Reviewed on Nov 6, 2026

El Conquistador Resort
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 $799 per night from Nov 10 to Nov 11
CA $799
CA $1,100 total
Nov 10 - Nov 11
includes taxes & fees
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
See all 2,260 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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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?
See properties

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 $1,280. 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.

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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.