
Roosevelt Roads Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Photo by Shannon Willitts
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Roosevelt Roads Vacation Deals
Price found within the past 48 hours. Click for updated prices.


The Oliver Hotel
San Juan Antiguo
Price was CA $1,922, price is now CA $935 per person
CA $935
per person
Nov 5 - Nov 12
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (33 reviews)
El hotel por dentro es muy bonito, el staff amable. Pero, como es nuevo necesitan estar mas al día con el mantenimiento (aires, inodoros, agua caliente, etc). También mejorar el manejo de los empleados de limpieza (debe hacer menos escándalo) y mejorar la comunicación con las personas de mantenimiento (horarios para hacerlo y si hay huéspedes en la habitación o no).
Reviewed on Aug. 9, 2025

San Agustin Apartments
San Juan Antiguo
Price was CA $2,476, price is now CA $1,224 per person
CA $1,224
per person
Nov 5 - Nov 12
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (370 reviews)
La propiedad en excelentes condiciones y ubicación perfecta
Reviewed on Aug. 23, 2025


Urbana Hotel
San Juan Antiguo
Price was CA $1,633, price is now CA $883 per person
CA $883
per person
Oct 8 - Oct 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (328 reviews)
The front desk staff was amazing, they welcomed us with champagne
Reviewed on Aug. 22, 2025
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
The price is CA $358 per night from Aug 26 to Aug 27
CA $358
CA $461 total
Aug 26 - Aug 27
includes taxes & fees
8.8/10 Excellent! (2,522 reviews)
"This property was beautiful. Grounds were well kept, staff always friendly. Bring your walking shoes oops I mean flip flops or sandals ( LOL), and if not no worries there- you can call for the fun golf cart rides at anytime. It is a fun, but quite place with everything you need right there. I traveled ..."
Reviewed on Aug. 23, 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard, Río Grande
Fully refundableReserve now, pay when you stay
The price is CA $413 per night from Aug 29 to Aug 30
CA $413
CA $560 total
Aug 29 - Aug 30
includes taxes & fees
8.4/10 Very Good! (2,143 reviews)
"The most beautiful place to stay especially if you plan on doing activities in the rainforest! 10/10 experience!"
Reviewed on Aug. 23, 2025

El Conquistador Resort
1000 Conquistador Avenue, Fajardo
Fully refundableReserve now, pay when you stay
The price is CA $347 per night from Aug 28 to Aug 29
CA $347
CA $476 total
Aug 28 - Aug 29
includes taxes & fees
9/10 Wonderful! (3,165 reviews)
"Needs more breakfast and lunch options in the Marina area. Love to stay at El Conquistador."
Reviewed on Aug. 24, 2025
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.
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
- Puerto Rico Island All Inclusive Resorts and Hotels
- Grand Cayman All Inclusive Resorts and Hotels
- Best Hotels in Puerto Rico Island
- Best Hotels in Grand Cayman
- Best Hotels in Antigua
- San Juan All Inclusive Resorts and Hotels
- Best Hotels in San Juan
- Puerto Rico Island Adults Only Resorts & Hotels
- Puerto Rico Island Mountain Hotels
- Hotels in Old San Juan
Cruises
Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.