Title: Cheap Vacations in Roosevelt Roads 2026/2026 | 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 Cheap Vacations ## 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 ## Flight and Cheap hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Wyndham Palmas Beach and Golf Boutique Resort](https://images.trvl-media.com/lodging/31000000/30080000/30079000/30078988/42731778_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Palmas Beach and Golf Boutique Resort CA $1,271 per person Feb 10 - Feb 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.4/10 Very Good! (651 reviews) Would happily come again Reviewed on Nov 28, 2025 ![Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)](https://images.trvl-media.com/lodging/6000000/5200000/5196300/5196263/66510c0c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only) Condado CA $2,376 per person Feb 23 - Feb 28 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to San Juan (SJU) 9/10 Wonderful! (645 reviews) Tatiana was a great host who helped us out tremendously. Reviewed on Nov 30, 2025 ![MARU by DW](https://images.trvl-media.com/lodging/113000000/112180000/112174900/112174847/60d84c71_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### MARU by DW Condado CA $2,275 per person Feb 10 - Feb 16 found 5 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (15 reviews) Supermarket near by a late night bite truck near by was very convenient neighborhood safe Reviewed on Oct 28, 2025 ![WALD HAUS by DW](https://images.trvl-media.com/lodging/77000000/76320000/76319300/76319249/ee96ef1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### WALD HAUS by DW CA $3,957 per person Jan 15 - Jan 19 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 10/10 Exceptional! (9 reviews) The property was very clean and beautifully decorated! Reviewed on Nov 2, 2025 ![DUNA by DW](https://images.trvl-media.com/lodging/79000000/78740000/78739700/78739626/83641b59_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DUNA by DW Santurce CA $1,975 per person Jan 7 - Jan 13 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 9.6/10 Exceptional! (58 reviews) Very clean and spacious. Reviewed on Nov 26, 2025 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/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Cheap holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![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 $3,348 per person Feb 23 - Feb 28 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to San Juan (SJU) 7.6/10 Good! (128 reviews) Bianca and Melanie at the front desk were both very helpful and accommodating. Reviewed on Sep 28, 2025 ![Wyndham Grand Rio Mar Rainforest Beach and Golf Resort](https://images.trvl-media.com/lodging/1000000/50000/41700/41642/0558d37f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Rio Mar Rainforest Beach and Golf Resort Mameyes II CA $3,496 per person Feb 23 - Feb 28 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to San Juan (SJU) 8.6/10 Excellent! (2,206 reviews) The National Park Rainforest is less than a 5 minute drive away. Excellent resort with lots of amenities. 2 Championship golf courses, tennis and pickle ball courts. Reviewed on Dec 4, 2025 ![Residences at Dorado Beach, a Ritz-Carlton Reserve](https://images.trvl-media.com/lodging/7000000/6670000/6668100/6668065/w4000h2664x0y0-f6932a75_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residences at Dorado Beach, a Ritz-Carlton Reserve Higuillar CA $35,930 per person Jan 7 - Jan 14 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 10/10 Exceptional! (2 reviews) Outstanding experience staying at one of the Residences. Definitely the best hotel in the Caribbeans. Reviewed on Sep 1, 2025 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/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap 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 $1,250 per person Feb 18 - Feb 21 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) My family and I stood for one night and it was a great hotel. When we first walked in you can immediately smell how clean it is. The staff were super sweet ! We had breakfast there and it was small BUT PERFECT for my family. We had ham, eggs, toast, waffle sticks. Our room itself was big and there was 5 of us. Beautiful hotel. Loved it Reviewed on Dec 4, 2025 ![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 $1,531 per person Jan 17 - Jan 20 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) The staff was amazing, best hotel stay I’ve had in awhile Reviewed on Nov 30, 2025 ![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 $1,422 per person Jan 17 - Jan 20 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (328 reviews) When it rained, the ceiling of Room 505 was leaking! Reviewed on Dec 1, 2025 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/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![THE BUOY](https://images.trvl-media.com/lodging/110000000/109800000/109790600/109790521/e2ad7744_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### THE BUOY Santurce CA $872 per person Feb 11 - Feb 15 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 10/10 Exceptional! (27 reviews) This property is more than complete, it's cozy, it's technological, it has much more than you can expect in any place because you have all appliances available, accessories to go to the beach like portable chairs and cooler, it's an apartment totally modern I loved it a lot Reviewed on Dec 1, 2025 ![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 $902 per person Jan 25 - Jan 29 found 14 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (50 reviews) Centrico, comodo, perfecto para estar cerca de todo y tener tranquilidad Reviewed on Nov 28, 2025 ![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 $2,014 per person Jan 21 - Jan 25 found 1 day ago Roundtrip flight included Calgary (YYC) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) The staff was amazing, best hotel stay I’ve had in awhile Reviewed on Nov 30, 2025 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/2026-01-05/2026-01-12/?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