Title: Roosevelt Roads Vacation Packages & Trips 2025/2026 from CA $799 | 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. ![Lazy Parrot Inn](https://images.trvl-media.com/lodging/1000000/910000/900400/900306/77384e02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lazy Parrot Inn CA $799 per person Feb 1 - Feb 8 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 18.4/10 Exceptional! (1,000 reviews) Staff were excellent. Room large with outside area. The rooster next door was a surprising early wake up about 5am but the coffee in the morning at 7.45am was very good . Reviewed on Nov 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-01/2026-02-08/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=900306&paandie=true&dealMarker=jkK0rioAJysPt6qNvRzaF0FajC5spMar07XhGOS25na2GYPxsATVJdxhp5YiPkvo) ![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 $2,345 per person Jan 1 - Jan 8 found 15 hours ago Roundtrip flight included Montreal (YMQ) to San Juan (SJU) 18.4/10 Exceptional! (589 reviews) There not that many options to choose from. Reviewed on Nov 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-01/2026-01-08/?FromAirport=YMQ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&dealMarker=aKz7sRAKaOzj6fIA5nQngwERPCNtjB6ICeJKIUSb0B_Pb9JnuP08j-PX5PTHbfqo) ![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 $1,091 per person Feb 4 - Feb 10 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 18/10 Exceptional! (50 reviews) Really was an easy check in/ out . Staff had no problem bringing new sheets or towels. No one really bothered. Reviewed on Oct 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-04/2026-02-10/?FromAirport=YMQ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107083384&paandie=true&dealMarker=jkK0rioAJysPt6qNvRzaF1MbUGo7kkVhcdV-0s7vTLS0yQsYzR7O75oApgKoXRlc) ![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 $1,738 per person Feb 7 - Feb 14 found 11 hours 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=i2NCFDq3dHYBg0WMrKyNUW9z_srPT_gMvVd8ULMbUnAcNqZ9o9q34Hwz2V5MLLWL) ![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 $1,809 per person Feb 4 - Feb 10 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 18/10 Exceptional! (326 reviews) The room was spotless and the staff were very attentive. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-04/2026-02-10/?FromAirport=YMQ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&dealMarker=jkK0rioAJysPt6qNvRzaF1MbUGo7kkVhcdV-0s7vTLRlwtkVI47Exol360ObM_o4) ![](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 Fully refundableReserve now, pay when you stay CA $319 CA $411 total Nov 30 - Dec 1 includes taxes & fees 8.8/10 Excellent! (2,778 reviews) Everything was great Reviewed on Nov 20, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%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 5 - Dec 6 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=05%2F12%2F2025&endDate=06%2F12%2F2025&selected=41642&PinnedHotelID=41642&HadPinnedHotel=true®ionId=6360451) [See all 2,107 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=24%2F11%2F2025&endDate=25%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 - Lodging - Flights - Packages - Cars - Vacation Rental - Other ### Lodging - [Cabezas Hotels](https://www.expedia.ca/Cabezas-San-Juan-Hotels.0-n553248635976173724-0.Travel-Guide-Filter-Hotels) - [Hotels near Carabali Rainforest Park](https://www.expedia.ca/Carabali-Rainforest-Park-Hotels.0-l553248621565183035-0.Travel-Guide-Filter-Hotels) - [Hotels near Ceiba Ferry Terminal](https://www.expedia.ca/Ceiba-Ferry-Terminal-Hotels.0-l553248635974547356-0.Travel-Guide-Filter-Hotels) - [Ceiba Hotels](https://www.expedia.ca/Ceiba-Hotels.d6025615.Travel-Guide-Hotels) - [Duque Hotels](https://www.expedia.ca/Duque-Hotels.d553248635976174171.Travel-Guide-Hotels) - [Hotels near El Yunque National Forest](https://www.expedia.ca/El-Yunque-National-Forest-Hotels.0-l6116646-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Fajardo](https://www.expedia.ca/Fajardo-Hotels-All-Inclusive-Hotel.0-0-d1191-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Fajardo Hotels](https://www.expedia.ca/Fajardo-Hotels.d1191.Travel-Guide-Hotels) - 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[Flights from Toronto (YYZ) to Vieques (VQS)](https://www.expedia.ca/lp/flights/yyz/vqs/toronto-to-vieques) ### Packages - [Azul Beach](https://www.expedia.ca/Azul-Beach-Mata-de-Platano.d6116648.Vacation-Attraction) - [Balneario de Carolina](https://www.expedia.ca/Balneario-De-Carolina-Isla-Verde.d553248635930543146.Vacation-Attraction) - [Baño Grande & Baño de Oro](https://www.expedia.ca/Bano-Grande-Bano-De-Oro-San-Juan.d553248621533158327.Vacation-Attraction) - [Bioluminescent Bay](https://www.expedia.ca/Bioluminescent-Bay-Puerto-Rico.d6116680.Vacation-Attraction) - [Black Sand Beach](https://www.expedia.ca/Black-Sand-Beach-Puerto-Rico.d6220312.Vacation-Attraction) - [Caguas Vacations](https://www.expedia.ca/Caguas.d6047341.Destination-Travel-Guides) - [Carolina Vacations](https://www.expedia.ca/Carolina.d180540.Destination-Travel-Guides) - [Coco Beach Golf and Country Club](https://www.expedia.ca/Coco-Beach-Golf-And-Country-Club-Zarzal.d553248635960526621.Vacation-Attraction) - [Condado Vacations](https://www.expedia.ca/Condado.d506189.Destination-Travel-Guides) - [Culebra Vacations](https://www.expedia.ca/Culebra.d912.Destination-Travel-Guides) - [El Yunque National Forest](https://www.expedia.ca/El-Yunque-National-Forest-Puerto-Rico.d6116646.Vacation-Attraction) - [Esperanza Vacations](https://www.expedia.ca/Esperanza.d6084481.Destination-Travel-Guides) - [Fajardo Vacations](https://www.expedia.ca/Fajardo.d1191.Destination-Travel-Guides) - [Visit Fajardo](https://www.expedia.ca/Fajardo.dx1191) - [Flamenco Beach](https://www.expedia.ca/Flamenco-Beach-Culebra.d6081849.Vacation-Attraction) - [Florida Vacations](https://www.expedia.ca/Florida.d6360440.Destination-Travel-Guides) - [Guaynabo Vacations](https://www.expedia.ca/Guaynabo.d6222271.Destination-Travel-Guides) - [Hiram Bithorn Stadium](https://www.expedia.ca/Hiram-Bithorn-Stadium-Hato-Rey-Norte.d502601.Vacation-Attraction) - [Isla Verde Vacations](https://www.expedia.ca/Isla-Verde.d6139938.Destination-Travel-Guides) - [La Chiva Beach](https://www.expedia.ca/La-Chiva-Beach-Puerto-Rico.d6116678.Vacation-Attraction) - [Visit Llave](https://www.expedia.ca/Llave.dx553248635976174103) - [Luquillo Beach](https://www.expedia.ca/Luquillo-Beach-San-Juan.d6081853.Vacation-Attraction) - [Luquillo Vacations](https://www.expedia.ca/Luquillo.d500171.Destination-Travel-Guides) - [Visit Luquillo](https://www.expedia.ca/Luquillo.dx500171) - [Museo de Arte de Puerto Rico](https://www.expedia.ca/Museo-De-Arte-De-Puerto-Rico-Santurce.d6081953.Vacation-Attraction) - [Palmas del Mar Beach](https://www.expedia.ca/Palmas-Del-Mar-Beach-Puerto-Rico.d6130038.Vacation-Attraction) - [Río Grande Vacations](https://www.expedia.ca/Rio-Grande.d500118.Destination-Travel-Guides) - [Visit Solimar](https://www.expedia.ca/San-Juan-Solimar.dx553248635976398783) - [Visit Vilomar](https://www.expedia.ca/San-Juan-Vilomar.dx553248635976398705) - [Visit Sector Los Ramos](https://www.expedia.ca/Sector-Los-Ramos.dx6360454) - [The Mall of San Juan](https://www.expedia.ca/The-Mall-Of-San-Juan-Oriente.d553248623748341398.Vacation-Attraction) - [University of Puerto Rico](https://www.expedia.ca/University-Of-Puerto-Rico-Rio-Piedras.d6116652.Vacation-Attraction) - [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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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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)