Title: Roosevelt Roads Vacation Packages & Trips 2025/2026 from CA $1,091 | 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. ![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 $1,091 per person Dec 14 - Dec 19 found 2 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2025-12-14/2025-12-19/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=116013898&paandie=true&dealMarker=73w_BNPqGYLQRy9HgIHmh2R1_1xmPpzI58bCDproLabhIX8-cX1BDxCzJBpV4WgA) ![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 $2,325 per person Nov 20 - Nov 27 found 1 day ago Roundtrip flight included Edmonton (YEG) 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/2025-11-20/2025-11-27/?FromAirport=YEG&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&dealMarker=DLHi-PMkVI7xxaZw0Dt0ThfPQPoDfSp-05hEMZEvEJAkcHTsCwdTCX--VmDDFLBr) ![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 $1,745 per person Nov 13 - Nov 20 found 1 day ago Roundtrip flight included Edmonton (YEG) to San Juan (SJU) 9/10 Wonderful! (266 reviews) Everything was excellent!! See you soon. Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-13/2025-11-20/?FromAirport=YEG&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&dealMarker=UyvDaWhSRqd9wriskB7tZB8buc2FKwXBGAxNAjndX-54EEICCBfM6FDyrLJ20sSk) ![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 $2,088 per person Nov 13 - Nov 20 found 1 day ago Roundtrip flight included Edmonton (YEG) to San Juan (SJU) 8.4/10 Very Good! (1,958 reviews) Service was great. Bartenders st the swim up bar were amazing Reviewed on Oct 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-13/2025-11-20/?FromAirport=YEG&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1592&paandie=true&dealMarker=UyvDaWhSRqd9wriskB7tZL9Q-jPte6dIj1LbQfWVrtAgDePcHJOpUw7bqAnY69Zx) ![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 $2,454 per person Dec 15 - Dec 22 found 12 hours ago Roundtrip non-stop flight included Montreal (YUL) 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/2025-12-15/2025-12-22/?FromAirport=YUL&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64577147&paandie=true&dealMarker=UjFOvCI3dKpOTUw1fr6A7QUaGJusD42idThnr54LZAhT_X9ud4GF1vcSVsiMOv7y) ## 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 $465 total Nov 3 - Nov 4 includes taxes & fees 8.8/10 Excellent! (2,664 reviews) "Ocean view was beautiful. Only thing we ran out of water for 3 hours but other than that it was pleasant staying there." Reviewed on Oct 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=03%2F11%2F2025&endDate=04%2F11%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 9/10 Wonderful! (3,188 reviews) "Super friendly staff and great hotel." Reviewed on Oct 7, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=23%2F10%2F2025&endDate=24%2F10%2F2025&selected=447559&PinnedHotelID=447559&HadPinnedHotel=true®ionId=6360451) [](https://expedia.ca/Hotel-Search?startDate=23%2F10%2F2025&endDate=24%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 Fully refundableReserve now, pay when you stay CA $576 CA $780 total Oct 13 - Oct 14 includes taxes & fees 8.4/10 Very Good! (2,189 reviews) "Great property! Very clean and staff was super friendly and helpful." Reviewed on Oct 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=41642&PinnedHotelID=41642&HadPinnedHotel=true®ionId=6360451) [See all 2,115 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F10%2F2025&endDate=11%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 - 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 to Luquillo](https://www.expedia.ca/Cheap-Flights-To-Luquillo.d500171.Travel-Guide-Flights) - [Flights from Antonio Rivera Rodriguez](https://www.expedia.ca/lp/airports/vqs/flights-from-antonio-rivera-rodriguez-airport) - [Flights from Anaa (AAA) to Vieques (VQS)](https://www.expedia.ca/lp/flights/aaa/vqs/anaa-to-vieques) - [Flights from Asheville (AVL) to Vieques (VQS)](https://www.expedia.ca/lp/flights/avl/vqs/asheville-to-vieques) - [Flights from Aguadilla (BQN) to Vieques (VQS)](https://www.expedia.ca/lp/flights/bqn/vqs/aguadilla-to-vieques) - [Flights from Culebra (CPX) to Vieques (VQS)](https://www.expedia.ca/lp/flights/cpx/vqs/culebra-to-vieques) - [Flights from Fajardo (FAJ) to Vieques (VQS)](https://www.expedia.ca/lp/flights/faj/vqs/fajardo-to-vieques) - [Flights from Indianapolis (IND) to Vieques (VQS)](https://www.expedia.ca/lp/flights/ind/vqs/indianapolis-to-vieques) - [Flights from La Ceiba (LCE) to Vieques (VQS)](https://www.expedia.ca/lp/flights/lce/vqs/la-ceiba-to-vieques) - 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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) - 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[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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