Title: Roosevelt Roads Vacation Packages & Trips 2025/2026 from CA $1,284 | Expedia.ca [Roosevelt Roads Travel Guide](https://expedia.ca/Roosevelt-Roads.dx6360451)[Hotels in Roosevelt Roads](https://expedia.ca/Roosevelt-Roads-Hotels.d6360451.Travel-Guide-Hotels)[Vacation Rentals in Roosevelt Roads](https://expedia.ca/Roosevelt-Roads-Vacation-Rentals.d6360451.Travel-Guide-VacationRentals)[Flights to Roosevelt Roads](https://expedia.ca/Cheap-Flights-To-Roosevelt-Roads.d6360451.Travel-Guide-Flights)[Roosevelt Roads Car Rentals](https://expedia.ca/Car-Rentals-In-Roosevelt-Roads.d6360451.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6360451/3441fe46-31f2-46bc-b307-613f9edf876d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Roosevelt Roads Vacation Packages ## 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 ## Top Roosevelt Roads Vacation Deals 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 $1,284 per person Feb 7 - Feb 14 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 18/10 Exceptional! (50 reviews) Excelente habitación!!! Muy espaciosa y cómoda. Muy buena localización. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-07/2026-02-14/?FromAirport=YMQ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107083384&paandie=true&dealMarker=iYhdhD_L5JGO8BheaqG_E3R5sw8d_0GtWpAbIqY4LlMhWlEBFAWRiHr0kwc5kM5r) ![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 $1,895 per person Feb 12 - Feb 18 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 18.4/10 Exceptional! (589 reviews) The hotel had a great location, super close to great restaurants. Staff was really friendly and the welcome drinks were a great start to our vacation. Breakfast was delicious! Very happy with our choice to stay here! Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-18/?FromAirport=YMQ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&dealMarker=i2NCFDq3dHYBg0WMrKyNUVXGTiDTVCZ02HSsqJACJcwaw5Hev6ZBswH20wAdDG5Y) ![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 $1,979 per person Feb 7 - Feb 14 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 17.2/10 Exceptional! (577 reviews) Excellent, was a wonderfull stay Reviewed on Nov 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-07/2026-02-14/?FromAirport=YMQ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&dealMarker=i2NCFDq3dHYBg0WMrKyNUcugR3dsv4pL2csiWnR5naml0acHqYbbfcjiLXvkWUhy) ![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 $1,775 per person Feb 7 - Feb 14 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 18/10 Exceptional! (500 reviews) Everything about my stay was wonderful. The staff were friendly and welcoming, and the room was spotless. The view was incredible—I could even see when the cruise ships came in. The food at the restaurant was delicious; I had the salmon, and it was cooked perfectly. They also have a great selection for dinner. The neighborhood felt safe and quiet, and it’s easy to walk around and explore. Overall, a 10/10 stay. Highly recommend! Reviewed on Nov 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-07/2026-02-14/?FromAirport=YMQ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&dealMarker=iYhdhD_L5JGO8BheaqG_E-2xcxjx7fz2ewv3vbhX_NumOqLSMj9aQF_iy2euVtLr) ![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 $2,173 per person Feb 7 - Feb 14 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 18/10 Exceptional! (328 reviews) The room was spotless and the staff were very attentive. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-07/2026-02-14/?FromAirport=YMQ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&dealMarker=i2NCFDq3dHYBg0WMrKyNUcugR3dsv4pL2csiWnR5nan_-o4fp1oX-RsUF1KQGgXj) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_6360451) ## Ready to book your vacation to Roosevelt Roads? Choose your dates ## Roosevelt Roads Hotel Deals ![Hyatt Regency Grand Reserve Puerto Rico](https://images.trvl-media.com/lodging/1000000/980000/979700/979694/08d6d09c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Grand Reserve Puerto Rico 200 Coco Beach Blvd. Highway 955-I Río Grande CA $329 CA $423 total Dec 2 - Dec 3 includes taxes & fees 8.8/10 Excellent! (2,778 reviews) Everything was great Reviewed on Nov 20, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F12%2F2025&endDate=03%2F12%2F2025&selected=979694&PinnedHotelID=979694&HadPinnedHotel=true®ionId=6360451) ![El Conquistador Resort](https://images.trvl-media.com/lodging/1000000/450000/447600/447559/926a31f3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### El Conquistador Resort 1000 Conquistador Avenue Fajardo Fully refundableReserve now, pay when you stay CA $430 CA $569 total Dec 1 - Dec 2 includes taxes & fees 9/10 Wonderful! (3,211 reviews) Definitely going to visit again Reviewed on Nov 21, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=447559&PinnedHotelID=447559&HadPinnedHotel=true®ionId=6360451) ![Wyndham Grand Rio Mar Rainforest Beach and Golf Resort](https://images.trvl-media.com/lodging/1000000/50000/41700/41642/0558d37f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham Grand Rio Mar Rainforest Beach and Golf Resort 6000 Rio Mar Boulevard Río Grande Fully refundableReserve now, pay when you stay CA $494 CA $668 total Dec 18 - Dec 19 includes taxes & fees 8.4/10 Very Good! (2,213 reviews) Pool excelente y el cuarto super comodo. Reviewed on Nov 20, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=41642&PinnedHotelID=41642&HadPinnedHotel=true®ionId=6360451) [See all 2,120 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F11%2F2025&endDate=27%2F11%2F2025®ionId=6360451) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](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) ## Explore a world of travel with Expedia - 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[Vieques Ferry Terminal](https://www.expedia.ca/Vieques-Ferry-Terminal-Vieques.d553248622519827039.Vacation-Attraction) - [Vieques Island Vacations](https://www.expedia.ca/Vieques-Island.d3734.Destination-Travel-Guides) - [Vieques Vacations](https://www.expedia.ca/Vieques.d6139918.Destination-Travel-Guides) - [Yunke Zipline Adventures](https://www.expedia.ca/Yunke-Zipline-Adventures-Mata-de-Platano.d553248621532873320.Vacation-Attraction) ### Cars - [Car rentals near Ceiba Ferry Terminal](https://www.expedia.ca/Car-Rentals-In-Ceiba-Ferry-Terminal.d553248635974547356.Car-Rental-Guide) - [Car rental Ceiba](https://www.expedia.ca/Car-Rentals-In-Ceiba.d6025615.Car-Rental-Guide) - [Car rental Fajardo](https://www.expedia.ca/Car-Rentals-In-Fajardo.d1191.Car-Rental-Guide) - [Car rental Luquillo](https://www.expedia.ca/Car-Rentals-In-Luquillo.d500171.Car-Rental-Guide) - [Enterprise Rental Cars in Ceiba](https://www.expedia.ca/Enterprise-Car-Rentals-In-Ceiba.d6025615-c15.Car-Rental-Guide-Suppliers) ### Vacation Rental - [Luquillo Vacation Rentals](https://www.expedia.ca/Luquillo-Vacation-Rentals.d500171.Travel-Guide-VacationRentals) ### Other - [Things to do in Ceiba](https://www.expedia.ca/Things-To-Do-In-Ceiba.d6025615.Travel-Guide-Activities) - [Things to do in Fajardo](https://www.expedia.ca/Things-To-Do-In-Fajardo.d1191.Travel-Guide-Activities) - [Things to do in Luquillo](https://www.expedia.ca/Things-To-Do-In-Luquillo.d500171.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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