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.
3 Bedroom Oceanfront Beach House

3 Bedroom Oceanfront Beach House

3.5 out of 5
Price was CA $2,591, price is now CA $1,632 per person
CA $1,632
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to San Juan (SJU)
9.6/10 Exceptional! (40 reviews)
The whole experience was just perfect I would definitely book again

Reviewed on Oct 27, 2026

Hotel Puerto Valdes

Hotel Puerto Valdes

4 out of 5
Puerta de Tierra
Save 100% on your flight
Price was CA $2,898, price is now CA $1,637 per person
CA $1,637
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)
Staff super friendly. Room is clean but property has no curtains or blinds in living room - and some flimsy curtains in bedroom. Air con is not best either.

Reviewed on Nov 12, 2026

Castillo Caribe by Otium

Castillo Caribe by Otium

2 out of 5
Condado
Price was CA $4,544, price is now CA $2,829 per person
CA $2,829
per person
Jan 20 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
No reviews

SELVA by DW

SELVA by DW

4 out of 5
Pitahaya
Price was CA $8,197, price is now CA $5,136 per person
CA $5,136
per person
Jan 29 - Feb 3
found 18 hours 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

WALD HAUS by DW

WALD HAUS by DW

4 out of 5
Price was CA $5,876, price is now CA $3,741 per person
CA $3,741
per person
Feb 4 - Feb 9
found 24 hours ago
Roundtrip non-stop 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

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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 $373 per night from Nov 30 to Dec 1
CA $373
CA $480 total
Nov 30 - Dec 1
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 $497 per night from Dec 7 to Dec 8
CA $497
CA $643 total
Dec 7 - Dec 8
includes taxes & fees
9.2/10 Wonderful! (3,681 reviews)
"."

Reviewed on Nov 11, 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
The price is CA $782 per night from Dec 13 to Dec 14
CA $782
CA $1,076 total
Dec 13 - Dec 14
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 $1,632. 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.