Title: Cheap Vacations in Roosevelt Roads 2025/2026 | 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 Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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. ![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 $1,734 per person Dec 2 - Dec 6 found 15 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (643 reviews) This has to be my #1 hotel experience ever. The staff was so great, environment very private and just awesome place and views. I will be back., Reviewed on Sep 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5196263&paandie=true&HotelClass=40&dealMarker=T5O_T8hQemw9aH9wDC3MZOPyr2izNS5F5rR9F1Imfe26QwDqawam8M18k4eLDTHl) ![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 $1,776 per person Jan 3 - Jan 9 found 1 day ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 9.2/10 Wonderful! (542 reviews) Very nice staff people, maybe the breakfast will be different every day, no always the same Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-03/2026-01-09/?FromAirport=YHM&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&HotelClass=40&dealMarker=l8stBhYiF08rqXVsw4uO8HY6UlDTyXLiIE00bfkRXvPscwysS6UOLN0vqBZl54Nz) ![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 $2,969 per person Jan 3 - Jan 9 found 19 hours ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 8.6/10 Excellent! (563 reviews) I absolutely LOVED this hotel. My stay was relaxing. It was peaceful, clean, the staff (front desk, housekeeping and restaurant staff) were kind. Hotel was 20mins or less to different locations I visited. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-03/2026-01-09/?FromAirport=YHM&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&HotelClass=40&dealMarker=6nD0Ijiq-hni4ULFn01xr64YaOKF2EXUTLIRwu0aQnZHfFc7nHq9ZVGkddq6MagN) ![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 $2,321 per person Jan 3 - Jan 9 found 1 day ago Roundtrip flight included Hamilton (YHM) to San Juan (SJU) 9/10 Wonderful! (489 reviews) Staff was amazing and attentive. My girls and I enjoyed our stay Reviewed on Oct 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-03/2026-01-09/?FromAirport=YHM&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&HotelClass=40&dealMarker=BxEtY3cKretVoaB3JZPhU2mBaw7v4D5wtoII3B7h9rYDJvCbk35TMOkY8w4hY23p) ![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 $3,905 per person Dec 10 - Dec 16 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 10/10 Exceptional! (8 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-10/2025-12-16/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=76319249&paandie=true&HotelClass=40&dealMarker=pKcOZOtltrHSlckQ4uUUDGk-oj3VTA4WOvhVTuVmURwGahbN53v1gomLKHPRlaEA) 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/2025-11-19/2025-11-26/?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. ![Condado Vanderbilt Hotel](https://images.trvl-media.com/lodging/10000000/9110000/9105300/9105241/2628fada_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Condado Vanderbilt Hotel Condado CA $1,632 per person Nov 20 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (1,602 reviews) Every thing was wonderful Reviewed on Oct 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-20/2025-11-24/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=9105241&paandie=true&HotelClass=50&dealMarker=py-Fj_2SrylB10S0FD4SFngk5PUcUuSVUsdYdvEs_BWx90jnpZsi04OozONraH4y) ![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 $1,838 per person Nov 20 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.4/10 Very Good! (2,018 reviews) I dont like to pay extra for use the parking lot Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-20/2025-11-24/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1592&paandie=true&HotelClass=50&dealMarker=py-Fj_2SrylB10S0FD4SFqrKt4A4f5tz-mhHNIIM7HzCcoNeU5iD7z39yGAIWlcl) ![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 $2,088 per person Nov 20 - Nov 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 7.6/10 Good! (127 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/2025-11-20/2025-11-24/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64577147&paandie=true&HotelClass=50&dealMarker=py-Fj_2SrylB10S0FD4SFpCTsp8nBQtdv5o0_l6vII3AAZPeBQEmdIQqRT5EL8y3) 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/2025-11-19/2025-11-26/?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. ![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 $1,626 per person Nov 28 - Dec 1 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 8.6/10 Excellent! (563 reviews) I absolutely LOVED this hotel. My stay was relaxing. It was peaceful, clean, the staff (front desk, housekeeping and restaurant staff) were kind. Hotel was 20mins or less to different locations I visited. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-01/?FromAirport=YUL&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&HotelClass=40&dealMarker=ATMUgjs41LG2rwO1MsSPdKKwJd9CQM7HLouRrdHvK06LKGXEh6MPowhP9vf1zxIr) ![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 $2,414 per person Dec 30 - Jan 2 found 16 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (542 reviews) Very nice staff people, maybe the breakfast will be different every day, no always the same Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-02/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&HotelClass=40&dealMarker=YrECUntz0aYVWoR8SqwNHZn2c-cRR47KGmH5TrOjxiWTZ3ttH6wDO5ycUGd3xUKG) ![Don Rafa Boutique Hotel & Residences](https://images.trvl-media.com/lodging/85000000/84360000/84351100/84351100/fa3a024b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Don Rafa Boutique Hotel & Residences Santurce CA $2,622 per person Dec 30 - Jan 2 found 16 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.4/10 Exceptional! (319 reviews) Great little hotel with fun interiors. Could use a light over the bathroom sink and better quality TP. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-02/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=84351100&paandie=true&HotelClass=40&dealMarker=2QMUqcKqEk04zqrBrXtSy2SuTip2-i4WHbL6ObugVSJqN_k_HDX_8SuhhYv7ygi7) 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/2025-11-19/2025-11-26/?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. ![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 $1,201 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 10/10 Exceptional! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=116013898&paandie=true&dealMarker=AHInqYT5nUKkZuSpv67nuUSap6SYCc3GQti6sfGEnCiNgpy9HZWA13fIRfaCXFzj) ![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 $2,811 per person Dec 30 - Jan 3 found 16 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.2/10 Wonderful! (542 reviews) Very nice staff people, maybe the breakfast will be different every day, no always the same Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-03/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104217135&paandie=true&dealMarker=YrECUntz0aYVWoR8SqwNHSnhOLAxiuCF-DjLCXhsJXRDpYMgLZBZ3gWGy4aCtJrC) ![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 $2,171 per person Dec 24 - Dec 28 found 15 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8.6/10 Excellent! (563 reviews) I absolutely LOVED this hotel. My stay was relaxing. It was peaceful, clean, the staff (front desk, housekeeping and restaurant staff) were kind. Hotel was 20mins or less to different locations I visited. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-28/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&dealMarker=ipk84oAnQL1UQuicwCTT4LtH8q5P9LTCo8geyE2F-B-k-kO5SOHCRqavePjN1VMM) 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/2025-11-19/2025-11-26/?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 ![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAE6UlEQVR4Xu3bMXIjNxBGYbAUMPQReJQ5GnQ0HYVHcKhAZVj9o4EeDIcsd7AOpPeSJcEGvskg7mpL+x8qx4U/EUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBS7ZCvcuhmq+/lr/aPL+ymLq19jKnvpdr+9plZjZNBQEBAejdbBQEBOSA13jVHWt++tU/7Y54o5NoHYmm2ngUCAgJigcTSDATEZ9W1I+cnnjSnlG+cgRwCASkgIB7IIRCfLd9fsefwY63d7Q8QkAIyhh8DsUD6IkgffgzEckT5UrETZ/pL73UKRIHEMAgIyJgCUSAxfEQi3/7e73htnxd6IOsdPwMBaSAgxw9AeiAg7Yis3fqstn/Yia+XDtU4GeRk6VCNk0FOlg7VOBnkZOlQjZNBTpYO1TgZ5GTpUI2TQU6WDtU4eYc8SycqO7Htrv1rXxbyKpAG8iSQCKSBPAkk+snI+PJsf7zZicp/vVpLa/flQtfULT5VINHdVut4B6JAFEh0t9U63oEoEPVTETvxMm/ve0d0oa9T+v/GW383p/R0pf89+PooICANBAQEBGTXDvmyiZgt5bZb8jteS7XPr4+i5k8CZXftgygQEJACMvIpC6SBzBPLYfu49u2TN/tk/5feXmycUzMQEJAeCMiYmoGAOKI+5+ba9Jtbm4bLzaZ8aeaPMvKz6jgXBASkgID0/Kw6zgUBccQvdJ9VutBPlvQord07ojt+G0/3NkctEBAQkMcTT5ZAQH4j0mxWiLbv0tJ3/rY2v+OvjxtPA1EgILupx0AUCMhu6rGfi+iqVvb+y07Ub1xvfeDuH9qJHwPRDwf6bq4ln7CNHghIAwEpICAg/UNrh+jE+PJcyq2v60LfbMmnVkRfsX2q7NzaX1kgICAgICAg/wFZlwZivdlPAmqzCXuUmFLTnYFoqYGAgICAgPRWxL8p9096c/t1Lnl7ty2P4m4cFS9BQPRJDwQEBMQCsXTHf/aruszZD0NsyU+MnwQ0dUxTMxAQkDg6AgFpICCeX+jqZm7tS9twY7tcm/L0z9APUxZIA7FAGggIyNn2X474iRff7ksn37qtccdPxJ/ON66BgID0FyAgD4GACIl8+/s40W/v0qd0oSu/0IXojvdsygMBAQGxQEBARkckZue6rn3l7jxRS/sT9cOBTa0PDAICAgICAvIcOfZmd7z+v/Gm4V5tcccv499d47wIBARkCQQkAgE56WueqO2l3MYnWopsqvkd39rdnm4XCMhJICAgFgjI17rPThSyfuvWlK59uXZi6VMXQ3zjGggIiL0CAdHGNRAQnRjtZg8nWvsTY6MvlZd3fI13ID0QkAYCAvK7EV3oOtG3Wxf7+HNuf++vnmWPAgLSQF4GYh+DNJCX/WrEloTYcLj7qWauvnVv/VF84wwEBMQ+AQEBARm9Rlrfrj7t9taUdfHv03O30pJXYxkEBGSXlrwayyAgILu05NVY/rlI5Ejr7jaWXyIKBGSsxEuQYyAgYyVeghz7PcjazVbf++vN7nhb0pS+T/tPArPnLggIyAikgayBgPy5QFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZLq5yD/AnBGx77jsrxyAAAAAElFTkSuQmCC)