Title: Adventure Vacations in Roosevelt Roads 2026 | Expedia.ca ![](https://images.trvl-media.com/place/6360451/3441fe46-31f2-46bc-b307-613f9edf876d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Roosevelt Roads Adventure Vacations ## 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 ## Flight and Adventure hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Ola Boutique Hotel](https://images.trvl-media.com/lodging/105000000/104220000/104217200/104217135/7963308f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ola Boutique Hotel Condado CA $834 per person May 2 - May 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Everything was great thanks to the wonderful staff. Reviewed on Feb 8, 2026 ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/0dc1a939_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,595 per person Apr 18 - Apr 25 found 10 hours ago Roundtrip non-stop flight included Montreal Metropolitan Airport (YHU) to San Juan (SJU) 9/10 Wonderful! (500 reviews) Staff was extremely friendly and helpful Reviewed on Feb 7, 2026 ![Aire de O:live](https://images.trvl-media.com/lodging/1000000/530000/527600/527599/8d4c39ed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aire de O:live Isla Verde CA $2,165 per person Apr 18 - Apr 25 found 10 hours ago Roundtrip non-stop flight included Montreal Metropolitan Airport (YHU) to San Juan (SJU) 9/10 Wonderful! (328 reviews) The room was exactly like The photo, very spacious and comfortable. The staff is friendly. I would stay again because of the room and location, food : the restaurants are pretty fancy and there is no room service or breakfast options ,I think if they had some sort of food service like they offered on the beach it would make the stay even better. Reviewed on Feb 9, 2026 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/29ce7de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $1,137 per person May 2 - May 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) Great experience, restaurant was amazing, the music from the roof top is a bit loud but the shut it down at 11pm Reviewed on Feb 10, 2026 ![Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)](https://images.trvl-media.com/lodging/6000000/5200000/5196300/5196263/66510c0c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only) Condado CA $1,575 per person Apr 25 - Apr 30 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (645 reviews) Room was nice but small with a curious layout. Whole facility was nice and staff were very courteous and efficient. Sister property next door has a nice restaurant Reviewed on Jan 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Condado Vanderbilt Hotel](https://images.trvl-media.com/lodging/10000000/9110000/9105300/9105241/2628fada_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Condado Vanderbilt Hotel Condado CA $1,496 per person May 2 - May 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Everything was perfect Reviewed on Feb 8, 2026 ![Fairmont El San Juan Villa Experience](https://images.trvl-media.com/lodging/65000000/64580000/64577200/64577147/f326ce2d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont El San Juan Villa Experience Isla Verde CA $2,014 per person May 1 - May 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 7.6/10 Good! (128 reviews) One of the best hotels in PR Reviewed on Jan 2, 2026 ![Fairmont El San Juan Hotel](https://images.trvl-media.com/lodging/1000000/10000/1600/1592/99d8d575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont El San Juan Hotel Isla Verde CA $2,198 per person Apr 28 - May 5 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 8.4/10 Very Good! (2,051 reviews) Overall stay was great, and the staff was very friendly. My one complaint would be the resort fee. I’ve never seen this at any other hotel, but it appears to be variable based on the room rate (I believe about 20%). As a result, the daily resort fee for my stay including tax was $142…that’s outrageous considering it barely includes anything (no breakfast or parking). I think other hotels in San Juan are similarly outrageous with the resort fees, but I’ve never seen that anywhere else. Reviewed on Feb 10, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)](https://images.trvl-media.com/lodging/6000000/5200000/5196300/5196263/66510c0c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only) Condado CA $1,221 per person Apr 29 - May 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (645 reviews) Room was nice but small with a curious layout. Whole facility was nice and staff were very courteous and efficient. Sister property next door has a nice restaurant Reviewed on Jan 24, 2026 ![Ola Boutique Hotel](https://images.trvl-media.com/lodging/105000000/104220000/104217200/104217135/7963308f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ola Boutique Hotel Condado CA $1,263 per person Mar 23 - Mar 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Everything was great thanks to the wonderful staff. Reviewed on Feb 8, 2026 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/29ce7de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $1,417 per person Mar 23 - Mar 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) Great experience, restaurant was amazing, the music from the roof top is a bit loud but the shut it down at 11pm Reviewed on Feb 10, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Coral by the Sea Hotel](https://images.trvl-media.com/lodging/2000000/1090000/1082600/1082589/5fc3c0fb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Coral by the Sea Hotel Isla Verde CA $560 per person May 2 - May 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 6.2/10 (1,951 reviews) Room was clean but outdated. Staff were very nice. Reviewed on Feb 11, 2026 ![Ola Boutique Hotel](https://images.trvl-media.com/lodging/105000000/104220000/104217200/104217135/7963308f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ola Boutique Hotel Condado CA $834 per person May 2 - May 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Everything was great thanks to the wonderful staff. Reviewed on Feb 8, 2026 ![The Oliver Hotel](https://images.trvl-media.com/lodging/108000000/107090000/107083400/107083384/2b5683ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Oliver Hotel San Juan Antiguo CA $732 per person May 2 - May 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (50 reviews) Great location to San Juan Old town. Hotel staff very helpful and room a nice size and clean. Had 2 night here before a cruise and would certainly recommend it. Reviewed on Feb 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Roosevelt Roads [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-11/2026-03-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## More Vacations Ideas [Flights to Roosevelt Roads ](https://expedia.ca/Cheap-Flights-To-Roosevelt-Roads.d6360451.Travel-Guide-Flights)[ Roosevelt Roads Hotels ](https://expedia.ca/Roosevelt-Roads-Hotels.d6360451.Travel-Guide-Hotels)[ Roosevelt Roads Vacation Rentals ](https://expedia.ca/Roosevelt-Roads-Vacation-Rentals.d6360451.Travel-Guide-VacationRentals)[ Roosevelt Roads Car Rentals ](https://expedia.ca/Car-Rentals-In-Roosevelt-Roads.d6360451.Car-Rental-Guide)[ Roosevelt Roads Vacations ](https://expedia.ca/Roosevelt-Roads.d6360451.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. 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