Roosevelt Roads Adventure Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Shannon Willitts
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Adventure hotel deals in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
El Oasis Hotel
Price was CA $1,911, price is now CA $1,256 per person
CA $1,256
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
9.4/10 Exceptional! (203 reviews)
Perfect place to disconnect and relax. Friendly staff, and clean facilities. The food at the restaurant was ok but nothing memorable. Will definitely book again.
Reviewed on May 17, 2026
Hotel Puerto Valdes
San Juan Antiguo
Price was CA $2,792, price is now CA $1,773 per person
CA $1,773
per person
Jul 22 - Jul 27
just found
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
8.8/10 Excellent! (662 reviews)
Staff were wonderful. So helpful and gave great suggestions on things to do and places to eat! Clean and well stocked kitchen. Nice rooftop area with hot tub. The hot tub could use an update or just cleaning. A few of the floor planks were loose and sticking up but this didn’t really cause any issues. Could use better pillows and maybe directions on how to use the coffee maker. Other than that would definitely recommend staying here.
Reviewed on May 20, 2026
Ocean Breeze Villa
San Juan Antiguo
Price was CA $2,325, price is now CA $1,593 per person
CA $1,593
per person
Jul 8 - Jul 13
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
8.8/10 Excellent! (13 reviews)
Clean, communicative host, great location. All you need.
Reviewed on May 21, 2026
OLV Fifty Five - Adults Only
Condado
Price was CA $3,066, price is now CA $2,111 per person
CA $2,111
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (664 reviews)
Place is excellent! Staff amazing and location 5 Stars
Reviewed on May 20, 2026
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all trips5* Adventure holidays in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Hotel
Isla Verde
Price was CA $1,735, price is now CA $1,310 per person
CA $1,310
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (2,090 reviews)
The staff was exceptional, night life was great, pools are beautiful and service around the pool is a plus. We love the Banyon Tree so that is an attraction. Only drawbacks were the room does not have a lot of lighting but that is really the vibe of the whole hotel. The halls were noisy after 10 pm at night, certainly not the hotel’s fault. Overall, truly a very special place and I can’t wait to come back!
Reviewed on May 16, 2026
Fairmont El San Juan Villa Experience
Isla Verde
Price was CA $2,356, price is now CA $1,748 per person
CA $1,748
per person
Jul 31 - Aug 4
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
7.6/10 Good! (143 reviews)
Room had some stains on the carpet that h
Reviewed on May 20, 2026
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all trips3 Night Adventure holidays in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Hotel
Isla Verde
Price was CA $1,984, price is now CA $1,570 per person
CA $1,570
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
8.6/10 Excellent! (2,090 reviews)
The staff was exceptional, night life was great, pools are beautiful and service around the pool is a plus. We love the Banyon Tree so that is an attraction. Only drawbacks were the room does not have a lot of lighting but that is really the vibe of the whole hotel. The halls were noisy after 10 pm at night, certainly not the hotel’s fault. Overall, truly a very special place and I can’t wait to come back!
Reviewed on May 16, 2026
Margaritaville Vacation Club by Wyndham - Rio Mar
Mameyes II
Price was CA $2,280, price is now CA $1,884 per person
CA $1,884
per person
Jun 25 - Jun 28
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
9/10 Wonderful! (291 reviews)
The room was very clean and staff was great.
Reviewed on May 17, 2026
El Conquistador Resort
Cabezas
Price was CA $2,119, price is now CA $1,760 per person
CA $1,760
per person
Jun 25 - Jun 28
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
9/10 Wonderful! (3,410 reviews)
Property was well maintained, pool bar was great with great music, friendly bartenders. Restaurants were ok but expensive. Drinks also at all the bars were expensive. It’s a great resort just come ready to SPEND. The restaurants outside of the resort were GREAT!!! Great authentic puerto rican at a fraction of the cost. An uber cost max. Of $12 to any restaurant.
Palomino beach was great with food and drinks available.
Reviewed on May 19, 2026
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all trips4 Night Adventure holidays in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Hotel Puerto Valdes
San Juan Antiguo
Price was CA $1,544, price is now CA $1,066 per person
CA $1,066
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.8/10 Excellent! (662 reviews)
Staff were wonderful. So helpful and gave great suggestions on things to do and places to eat! Clean and well stocked kitchen. Nice rooftop area with hot tub. The hot tub could use an update or just cleaning. A few of the floor planks were loose and sticking up but this didn’t really cause any issues. Could use better pillows and maybe directions on how to use the coffee maker. Other than that would definitely recommend staying here.
Reviewed on May 20, 2026
Isla Verde Beachfront Retreat With Parking
Isla Verde
Price was CA $2,398, price is now CA $1,419 per person
CA $1,419
per person
Jul 31 - Aug 4
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
10/10 Exceptional! (1 review)
The room was clean and spacious!
Reviewed on Mar 24, 2026
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt Roads
View all tripsMore vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
