Title: Mountain 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 Mountain 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 Mountain 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 $868 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (542 reviews) Clean room, helpful and friendly staff Reviewed on Oct 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&HotelClass=40&dealMarker=QXQ5CKBEfcG08VxKG3nPx5wfHyHj-yp_zBLvmMz2U_kiLW3FuMXtcmTz_CZu4stl) ![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 $1,159 per person Dec 5 - Dec 12 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (100 reviews) The property is perfect to couples and relaxing days Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-05/2025-12-12/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104571256&paandie=true&HotelClass=40&dealMarker=t774Nf__cBaUv00nPoSZb2GpwPlphUaoon6y94bev9P7WtRstX7HR43RQz4JZjIT) ![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 $1,097 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (489 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/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&HotelClass=40&dealMarker=QXQ5CKBEfcG08VxKG3nPx6dCzV9kHwEK93Fl30t2GVavzs8LFGFSpxiCQhki4KCc) ![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 $1,173 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (290 reviews) Lovely hotel &services Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&HotelClass=40&dealMarker=QXQ5CKBEfcG08VxKG3nPxzJZbbtFMXxXHg9ohhFfY0ORErmyOkQMBR7ttnoLrxdm) ![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 $2,097 per person Jan 4 - Jan 10 found 1 hour ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.6/10 Excellent! (563 reviews) I absolutely LOVED this hotel. My stay was relaxing. It was peaceful, clean, the staff (front desk, housekeeping and restaurant staff) were kind. Hotel was 20mins or less to different locations I visited. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-10/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&HotelClass=40&dealMarker=n_CuX-7g8R0k4RH8HZ7Lql1lYXlm4-qDpLrw_8cXPrwklPxjGLtSdxorRw1qcSKJ) 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/2025-11-23/2025-11-30/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Wyndham Grand Rio Mar Rainforest Beach and Golf Resort](https://images.trvl-media.com/lodging/1000000/50000/41700/41642/dbe15866_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Rio Mar Rainforest Beach and Golf Resort Mameyes II CA $2,567 per person Jan 12 - Jan 19 found 7 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.6/10 Excellent! (2,201 reviews) Overall good experience Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-19/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=41642&paandie=true&HotelClass=50&dealMarker=yNB2h_pFxDRldb2Q2f4szvCjhHMzMVPHIolI7D54rl412g0UsQb0NY8GJrZS8Jxi) ![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 $3,761 per person Jan 12 - Jan 19 found 7 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 7.6/10 Good! (127 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/2026-01-12/2026-01-19/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64577147&paandie=true&HotelClass=50&dealMarker=yNB2h_pFxDRldb2Q2f4szvX_E8cJLWA22xWLHS5MsOqtziTtTBnlbIw644UhvbEj) ![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 $3,246 per person Jan 12 - Jan 19 found 7 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.4/10 Very Good! (2,018 reviews) Lovely place,I will be back. Only thing I would change is being able to have separate tickets at the Meat Market Reviewed on Oct 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-19/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1592&paandie=true&HotelClass=50&dealMarker=yNB2h_pFxDRldb2Q2f4sztFGVG952IeAvWtXHaDs63_JZH6q8xzA8BPmGMgarNzY) 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/2025-11-23/2025-11-30/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain 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 $605 per person Dec 9 - Dec 12 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.2/10 Wonderful! (542 reviews) Clean room, helpful and friendly staff Reviewed on Oct 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-09/2025-12-12/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&HotelClass=40&dealMarker=yNB2h_pFxDRldb2Q2f4szgq97RJR-lEa0NHyr3j9EgTGcLWDkrJ4wTDOMJ5tqbt9) ![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 $871 per person Dec 6 - Dec 9 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (489 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/2025-12-06/2025-12-09/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&HotelClass=40&dealMarker=PgggDa00rBNrdIRQy1luJVJeyres2N2t8BOyrz-eQv5vlHBj1I0kqRgl_zCw01gs) ![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 $1,056 per person Jan 13 - Jan 16 found 4 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8.6/10 Excellent! (563 reviews) I absolutely LOVED this hotel. My stay was relaxing. It was peaceful, clean, the staff (front desk, housekeeping and restaurant staff) were kind. Hotel was 20mins or less to different locations I visited. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-13/2026-01-16/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&HotelClass=40&dealMarker=Xo0JhbY9uCDArxz_s4jPfFHO7H8-HjEk_-ZXPR1MrJrVwzuwnz63TxSeA0XcVqlu) 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/2025-11-23/2025-11-30/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/0dc1a939_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,097 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (489 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/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&dealMarker=QXQ5CKBEfcG08VxKG3nPx6dCzV9kHwEK93Fl30t2GVavzs8LFGFSpxiCQhki4KCc) ![Dorado Beach 5 Bedroom Villa](https://images.trvl-media.com/lodging/117000000/116020000/116013900/116013898/413e7713_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dorado Beach 5 Bedroom Villa Higuillar CA $1,163 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 10/10 Exceptional! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=116013898&paandie=true&dealMarker=zsdb7AqbqTyQd7e-XzjFS_dNWlq6udjY_7zZafkPltC1ON5gtZt6e3xYlk8bidSJ) ![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 $1,173 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (290 reviews) Lovely hotel &services Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&dealMarker=QXQ5CKBEfcG08VxKG3nPxzJZbbtFMXxXHg9ohhFfY0ORErmyOkQMBR7ttnoLrxdm) 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/2025-11-23/2025-11-30/?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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)