Title: Fishing 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 Fishing 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 Fishing hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,228 per person May 9 - May 13 found 4 hours ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 8.8/10 Excellent! (623 reviews) Great staff! Very nice and willing to be flexible Reviewed on Apr 3, 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 $1,395 per person Jun 19 - Jun 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (758 reviews) I enjoyed my stay with Ola Boutique. The staff was very helpful snd accommodating. The location was just perfect snd central for what I needed. Reviewed on Apr 6, 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 $1,682 per person May 15 - May 20 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (498 reviews) Great stay, great service, great staff, great view! Reviewed on Apr 7, 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 $1,799 per person May 15 - May 20 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (662 reviews) Very attentive staff, cozy rooms well designed for small spaces. Reviewed on Apr 4, 2026 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/b19a94ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $2,025 per person May 15 - May 20 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 8.6/10 Excellent! (634 reviews) The pool and upstairs lounge area was great, but the rooms did not match the cost. They need to replace several fixtures in the bedroom but the balcony view was nice this felt like a 3-star but charged 4 star prices. Reviewed on Mar 16, 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/2026-05-07/2026-05-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Fishing holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Hugo's Rental](https://images.trvl-media.com/lodging/109000000/108770000/108768900/108768837/ee9f8bbb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hugo's Rental Old San Juan CA $1,614 per person Jun 14 - Jun 21 found 2 hours ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (318 reviews) The price was good. The room was clean and A/C worked well. We chose to stay both before and after our cruise and both rooms were very comfortable. On return, we had requested a 1st floor room for ease and it was greatly appreciated when this was provided. We would recommend staying here especially if going on a cruise since it's so close to the port and theire is tons of shopping/dinig options available. Reviewed on Apr 7, 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 $2,596 per person May 15 - May 20 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 7.6/10 Good! (138 reviews) The beach was nice but the lounge chair cushions were filthy …. The casino customer service was mediocre Reviewed on Mar 24, 2026 ![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 $2,045 per person May 7 - May 12 found 19 hours ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (1,694 reviews) Property is very well taken care of, staff is lovely, lots of food options. Would book again. Gym is excellent. Great spa too! Reviewed on Apr 5, 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/2026-05-07/2026-05-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Fishing holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $960 per person May 9 - May 12 found 18 hours ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 8.8/10 Excellent! (623 reviews) Great staff! Very nice and willing to be flexible Reviewed on Apr 3, 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 $1,380 per person May 15 - May 18 found 20 hours ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 9.2/10 Wonderful! (498 reviews) Great stay, great service, great staff, great view! Reviewed on Apr 7, 2026 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/b19a94ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $1,678 per person Jun 25 - Jun 28 found 1 day ago Roundtrip flight included Toronto (YYZ) to San Juan (SJU) 8.6/10 Excellent! (634 reviews) The pool and upstairs lounge area was great, but the rooms did not match the cost. They need to replace several fixtures in the bedroom but the balcony view was nice this felt like a 3-star but charged 4 star prices. Reviewed on Mar 16, 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/2026-05-07/2026-05-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Fishing holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,228 per person May 9 - May 13 found 4 hours ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 8.8/10 Excellent! (623 reviews) Great staff! Very nice and willing to be flexible Reviewed on Apr 3, 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 $1,395 per person Jun 19 - Jun 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (758 reviews) I enjoyed my stay with Ola Boutique. The staff was very helpful snd accommodating. The location was just perfect snd central for what I needed. Reviewed on Apr 6, 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 $1,723 per person May 27 - May 31 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (498 reviews) Great stay, great service, great staff, great view! Reviewed on Apr 7, 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/2026-05-07/2026-05-14/?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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