Title: Scuba Diving Vacations in Roosevelt Roads 2025/2026 | 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 Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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. ![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 $1,291 per person Nov 15 - Nov 22 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (485 reviews) Staff was amazing and attentive. My girls and I enjoyed our stay Reviewed on Oct 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-15/2025-11-22/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&HotelClass=40&dealMarker=EPwHEExh2brC5bS9pHFRHsg88I1eo_ETkltmlDHlWofHp1kuoJNmNKTAZM6YlaHs) ![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 $1,585 per person Nov 15 - Nov 22 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (266 reviews) Construction going on while we were there. Only negative of our stay. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-15/2025-11-22/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&HotelClass=40&dealMarker=EPwHEExh2brC5bS9pHFRHvcYK8AKXqAa6iPhY3CAgIC_JT1vwFOF6GLCSDwoRaV-) ![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 $1,925 per person Nov 15 - Nov 22 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.4/10 Very Good! (1,958 reviews) Beautiful. Clean. Spacious. Tropical. Direct access to ocean & beach. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-15/2025-11-22/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1592&paandie=true&HotelClass=40&dealMarker=EPwHEExh2brC5bS9pHFRHmd0qG6Y8AL-lAzk6fjKR5XzNnO1fpW7zFhyPI_3P4tI) ![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 $2,669 per person Dec 18 - Dec 25 found 1 day ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 8.8/10 Excellent! (545 reviews) This hotel is very beautiful yet the cleaning staff only makes the bed. I’ve complained numerous times about the cleanliness of my room. The staff was amazing the manager Jay was very accommodating and the staff were all helpful and nice. Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-18/2025-12-25/?FromAirport=YHM&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&HotelClass=40&dealMarker=cfufaGy-MpODL6L50svJ0hTWXOccNqDszW19tw6YyFSxuI_zeE1U1ncocT_2exh6) ![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 $2,420 per person Nov 28 - Dec 5 found 23 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 7.6/10 Good! (125 reviews) Bianca and Melanie at the front desk were both very helpful and accommodating. Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-05/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64577147&paandie=true&HotelClass=40&dealMarker=1EdRzsPuihSR3a-mO5pkt60hd7VgyBK-rZiwhLKAV3EZGXfgbpszongP9FSlrgBk) 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/2025-11-16/2025-11-23/?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. ![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 $1,925 per person Nov 15 - Nov 22 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.4/10 Very Good! (1,958 reviews) Beautiful. Clean. Spacious. Tropical. Direct access to ocean & beach. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-15/2025-11-22/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1592&paandie=true&HotelClass=50&dealMarker=EPwHEExh2brC5bS9pHFRHmd0qG6Y8AL-lAzk6fjKR5XzNnO1fpW7zFhyPI_3P4tI) ![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 $2,420 per person Nov 28 - Dec 5 found 23 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 7.6/10 Good! (125 reviews) Bianca and Melanie at the front desk were both very helpful and accommodating. Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-05/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64577147&paandie=true&HotelClass=50&dealMarker=1EdRzsPuihSR3a-mO5pkt60hd7VgyBK-rZiwhLKAV3EZGXfgbpszongP9FSlrgBk) ![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 $1,943 per person Nov 15 - Nov 22 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (1,584 reviews) Every thing was wonderful Reviewed on Oct 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-15/2025-11-22/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=9105241&paandie=true&HotelClass=50&dealMarker=cdXjr3OgXk-jcS-sk2zTI-dgDVFqZ1dVO3yhIo4OcInoeSkEOYlXuyFSeS23m6SR) 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/2025-11-16/2025-11-23/?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 $976 per person Jan 11 - Jan 14 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to San Juan (SJU) 9/10 Wonderful! (498 reviews) We had a great time. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-14/?FromAirport=YOW&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&HotelClass=40&dealMarker=gWoCY9ybBvAlSa9__UL2RsyaHMI_XEyribLR3V9zisAReOqNNjrQ9JaZpTTfpXF3) ![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 $1,327 per person Jan 11 - Jan 14 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to San Juan (SJU) 9/10 Wonderful! (266 reviews) Construction going on while we were there. Only negative of our stay. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-11/2026-01-14/?FromAirport=YOW&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&HotelClass=40&dealMarker=P4s7Hbaa8Nha_LtxlR1gc6Qx4BCehGBhvsWfrrWWUeO7iRtHCo3A7pv_ZUlBiN1C) ![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 $1,649 per person Nov 28 - Dec 1 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 8.8/10 Excellent! (545 reviews) This hotel is very beautiful yet the cleaning staff only makes the bed. I’ve complained numerous times about the cleanliness of my room. The staff was amazing the manager Jay was very accommodating and the staff were all helpful and nice. Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-01/?FromAirport=YUL&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&HotelClass=40&dealMarker=KgpMqfncTYz4QjK7s9NyBxIfIat5OM-9BC22nZRZ_Xk32k6ahOwVazfzLoqBCY2G) 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/2025-11-16/2025-11-23/?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. ![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 $1,113 per person Dec 22 - Dec 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (36 reviews) Everything very nice and clean. There is no permanent staff manning the front desk, but they are a call and a couple of minutes away. The area, Puerta de Tierra, is very safe and within walkable distance to El Viejo San Juan. Only complaint: at arriving, on Thursday, I let the front desk to know that it was my wife birthday the following Saturday, and ask for their help to prepare a small surprise for my wife (that I was going to pay for). The following day I was told that the owners, due to their religion, do not celebrate birthdays. I found that a weird reason. It is their religion, not mine, and I didn’t want them to celebrate anything, I was the one celebrating my wife birthday. Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-26/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107083384&paandie=true&dealMarker=cnEzPXNCoF5zc6B5aXxn3eCx--Tcu7nTNNPPxNt1_78TIdM68-tvUEK8quqg13Ow) ![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 $1,225 per person Dec 22 - Dec 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (498 reviews) We had a great time. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-26/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&dealMarker=cnEzPXNCoF5zc6B5aXxn3eCx--Tcu7nTNNPPxNt1_7-F59U4R_r0hQfzPo6_Ff2u) ![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 $1,458 per person Dec 10 - Dec 14 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.8/10 Excellent! (545 reviews) This hotel is very beautiful yet the cleaning staff only makes the bed. I’ve complained numerous times about the cleanliness of my room. The staff was amazing the manager Jay was very accommodating and the staff were all helpful and nice. Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-10/2025-12-14/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&dealMarker=cdXjr3OgXk-jcS-sk2zTI0lNaEegA4UtH1VAE9a8ojktgR0nt9PB_uSf_jiU9pwW) 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/2025-11-16/2025-11-23/?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. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)