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.
WALD HAUS by DW
Price was CA $5,412, price is now CA $3,581 per person
CA $3,581
per person
Dec 9 - Dec 15
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Don Rafa Boutique Hotel & Residences
Santurce
Price was CA $6,230, price is now CA $4,274 per person
CA $4,274
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to San Juan (SJU)
9.4/10 Exceptional! (568 reviews)
El hotel es precioso y los empleados super serviciales, lo único que cierran el acceso a la piscina a las 7pm cuando el check-in es a las 4pm, a lo que te acomodas pierdes 1 día de disfrutar en la piscina. El estacionamiento está demasiado caro, deberían de bajarlo, porque lo que cobran por noche es exagerado. Por lo demás todo excelente 😊
Reviewed on Nov 5, 2026
SELVA by DW
Pitahaya
Price was CA $5,967, price is now CA $4,270 per person
CA $4,270
per person
Dec 9 - Dec 15
found 1 hour 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
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.
Residences at Dorado Beach, a Ritz-Carlton Reserve
Higuillar
Save 100% on your flight
Price was CA $25,634, price is now CA $20,408 per person
CA $20,408
per person
Jan 7 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
10/10 Exceptional! (2 reviews)
Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans.
Reviewed on Sep 1, 2025
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.
Condado Ocean Club - Adults Only
Condado
Price was CA $1,597, price is now CA $1,317 per person
CA $1,317
per person
Jan 7 - Jan 10
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to San Juan (SJU)
9/10 Wonderful! (1,685 reviews)
Great staff! Bar and restaurant are worth it
Reviewed on Nov 3, 2026
San Juan Marriott Resort and Stellaris Casino
Condado
Price was CA $1,800, price is now CA $1,523 per person
CA $1,523
per person
Jan 7 - Jan 10
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to San Juan (SJU)
9/10 Wonderful! (1,783 reviews)
The ocean views from our Cabana side room were lovely. We enjoyed the staffed pool and hot tub almost every day. The location is great for catching quick rides to Old San Juan, or nearby beaches. Also great are all the beaches, restaurants and shops that are walkable.
Reviewed on Nov 5, 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.
Aquatika Paraiso Tropical
Medianía Alta
Price was CA $1,325, price is now CA $933 per person
CA $933
per person
Dec 7 - Dec 11
just found
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
8.4/10 Very good! (280 reviews)
The apartment was clean and spacious. The one issue I had was all of the bedding was dirty we had to wash all bedding before sleeping in it. The washer is small so washing bedding in it was a chore. Overall the pools and grounds were amazing!! Definitely recommend
Reviewed on Nov 2, 2026
Ocean Breeze Villa
Puerta de Tierra
Price was CA $2,222, price is now CA $1,618 per person
CA $1,618
per person
Jan 7 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.2/10 Wonderful! (40 reviews)
Everything was great !!! Wonderful stay !!!
Reviewed on Nov 4, 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.
