Title: Scuba Diving Vacations in Roosevelt Roads 2026/2026 | 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 Scuba Diving 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 Scuba Diving hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Romeo Gay Hotel](https://images.trvl-media.com/lodging/105000000/104580000/104571300/104571256/c3574a90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Romeo Gay Hotel San Juan Antiguo CA $870 per person Jan 25 - Jan 30 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (121 reviews) Super convenient location, bar across the street, convenience store and liquor across the street The bar “5” across the street has pool table and Jenna games, super cool. All entrances with gate security codes, common area to work and leave suitcase before and after check in/out Very close to port and old San Juan. Isla verde and condado 10 minute drive ( if that far) We had an amazing time. We travel with family Reviewed on Dec 6, 2025 ![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 $1,253 per person Jan 25 - Jan 30 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Very welcoming & clean Reviewed on Dec 8, 2025 ![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 $894 per person Jan 25 - Jan 30 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (500 reviews) Really nice apartment with a great view, we could live there. 5-10 minute walk to old town shops and restaurants, as well as cruise terminal. Reviewed on Dec 8, 2025 ![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 $2,639 per person Jan 11 - Jan 18 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Yes the beach was across from the hotel. Reviewed on Dec 8, 2025 ![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 $2,764 per person Mar 1 - Mar 8 found 1 hour ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (645 reviews) Tatiana was a great host who helped us out tremendously. Reviewed on Nov 30, 2025 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/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Scuba Diving 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 $3,083 per person Jan 11 - Jan 18 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) Staff was fantastic and the service was great. We also had a very comfortable stay. The only negatives were that the AC in our room did not work very well (It kept turning off in the middle of the night) and there was a wedding reception on the 2nd floor that was so loud that we could hear the music all night long on the 5th floor. There were 4 weddings while we were there, I think the DJ for that one just had the music way too loud, because we were not bothered on other nights. The property is beautiful and the restaurants are great. The gym is also very nice and the spa is top notch. We will stay here again. Reviewed on Dec 6, 2025 ![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 $3,467 per person Feb 10 - Feb 15 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to San Juan (SJU) 7.6/10 Good! (128 reviews) Bianca and Melanie at the front desk were both very helpful and accommodating. Reviewed on Sep 28, 2025 ![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 $3,829 per person Jan 11 - Jan 18 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to San Juan (SJU) 8.4/10 Very Good! (2,051 reviews) Beautiful resort. Sad we only had one night to stay as we were traveling through to another island. Reviewed on Dec 8, 2025 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/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Scuba Diving holidays 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 $1,244 per person Mar 6 - Mar 9 found 8 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Very welcoming & clean Reviewed on Dec 8, 2025 ![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 $1,793 per person Feb 27 - Mar 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (645 reviews) Tatiana was a great host who helped us out tremendously. Reviewed on Nov 30, 2025 ![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 $1,694 per person Mar 6 - Mar 9 found 8 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again. Reviewed on Dec 6, 2025 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/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Scuba Diving holidays 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 $821 per person Feb 22 - Feb 26 found 9 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) Very welcoming & clean Reviewed on Dec 8, 2025 ![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 $959 per person Feb 22 - Feb 26 found 9 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (50 reviews) Hotel was quit ,and clean on arrival but you need to ask to clean the room, asked for towels and cream for coffee. Got the towels an hour later never got cream . No one at front desk, need to call for assistance Reviewed on Dec 8, 2025 ![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 $1,346 per person Feb 22 - Feb 26 found 9 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (328 reviews) Yes the beach was across from the hotel. Reviewed on Dec 8, 2025 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/2026-01-09/2026-01-16/?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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