Title: Roosevelt Roads Vacation Packages & Trips 2025/2026 from CA $708 | 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. ![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 $708 per person Nov 10 - Nov 14 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (498 reviews) Had an excellent stay at Ola boutique- I can not say enough about the hospitality we received. We would absolutely stay again ! Reviewed on Oct 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-10/2025-11-14/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&dealMarker=ergcRkbvQ132oav0knEnnLTAKokG_tv97JZieY6W-wYo2gVwOEz5hwmJ040-TVH5) ![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 $1,368 per person Nov 9 - Nov 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-15/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=116013898&paandie=true&dealMarker=6G4VshBxpt1VGdnGDnuoqges1TEw8ieqeWKZrqZFJs_z7mCe8HZ-tz_ZDUGib6kZ) ![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 $1,496 per person Nov 9 - Nov 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.8/10 Excellent! (545 reviews) Beautiful rooms. Grsat amenities. Amazing hot tub Reviewed on Sep 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-15/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&dealMarker=ergcRkbvQ132oav0knEnnCSpQpi6cHYTGf5aOyzbp-yIYY9dQAZtFZOwJY1OPK0H) ![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 $956 per person Nov 9 - Nov 15 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/2025-11-09/2025-11-15/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107083384&paandie=true&dealMarker=sUw9dzxM8YgHgyVbJGebj_M6XlicagYptOJmBPMjXYn7MXaQljTHX4rxNijPPM20) ![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 $1,215 per person Nov 9 - Nov 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (485 reviews) Beautiful intimate hotel in a great location. Staff was great and super helpful at all times. Definitely would stay here again. Reviewed on Sep 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-09/2025-11-15/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&dealMarker=sUw9dzxM8YgHgyVbJGebj1NAKL_iEHkY3RZWww_ZSvwSziGXYDTteTha5wpCeayG) ## 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 $361 CA $464 total Oct 5 - Oct 6 includes taxes & fees 8.8/10 Excellent! (2,659 reviews) "Great view" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%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 $400 CA $535 total Oct 5 - Oct 6 includes taxes & fees 9/10 Wonderful! (3,200 reviews) "This is hands down the most beautiful and spectacular hotel in all of Puerto" Reviewed on Sep 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%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/dbe15866_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham Grand Rio Mar Rainforest Beach and Golf Resort 6000 Rio Mar Boulevard, Río Grande CA $640 CA $866 total Oct 19 - Oct 20 includes taxes & fees 8.4/10 Very Good! (2,191 reviews) "I had a wonderful stay" Reviewed on Sep 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=41642&PinnedHotelID=41642&HadPinnedHotel=true®ionId=6360451) [See all 2,108 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F10%2F2025&endDate=04%2F10%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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