Title: All inclusive Vacations in Roosevelt Roads 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 All inclusive 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 All inclusive hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![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 $811 per person Feb 22 - Feb 27 found 18 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (500 reviews) The room was clean and the staff polite but it wasn’t luxury. First off, we messaged the hotel a few days in advance for a late check and when I messaged on check in day I was told the hotel was full and that we couldn’t. Also, we booked the penthouse which seemed ok until you learn the restaurant is right next to your room and the restaurant thinks it’s a night club. Or when the fire alarm goes off from the kitchen smoke. It’s a shame because the people are nice and the location is good so we gave 3 stars for that Reviewed on Dec 20, 2025 ![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 $1,195 per person Jan 25 - Jan 31 found 15 hours ago Roundtrip non-stop flight included Hamilton (YHM) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) LOVED this property!! Staff was great and helpful with any questions or concerns we had. Breakfast was fresh and had a variety of selection. Location is super convenient, there was a 24 hr grocery store across the street and walkable to plenty of food & exploration options. Good location for getting around San Juan and to El Yunque. Would stay again! Reviewed on Dec 21, 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 $1,496 per person Jan 25 - Jan 30 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again. Reviewed on Dec 6, 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 $1,605 per person Jan 25 - Jan 30 just found Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (645 reviews) Tatiana was a great host who helped us out tremendously. 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 $2,129 per person Jan 25 - Jan 31 found 17 hours ago Roundtrip non-stop flight included Hamilton (YHM) to San Juan (SJU) 9/10 Wonderful! (328 reviews) The roooooommmm! The room is EVERYTHING! The staff is amazing. The rooftop restaurant has great food. But the room just took it over the top. I absolutely love this hotel. Will definitely be staying here again when I return Reviewed on Dec 17, 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/2026-01-21/2026-01-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive 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 $2,558 per person Jan 25 - Jan 31 found 15 hours ago Roundtrip non-stop flight included Hamilton (YHM) to San Juan (SJU) 9.2/10 Wonderful! (1,616 reviews) The stay was excellent. The staff was attentive, friendly and prompt. Reviewed on Dec 19, 2025 ![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 $4,199 per person Feb 21 - Feb 28 found 2 hours ago Roundtrip non-stop flight included Montreal (YUL) 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 ![The St. Regis Bahia Beach Resort, Puerto Rico](https://images.trvl-media.com/lodging/4000000/3810000/3800200/3800119/f088cdb4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The St. Regis Bahia Beach Resort, Puerto Rico Herreras CA $6,248 per person Feb 15 - Feb 20 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.4/10 Exceptional! (450 reviews) Beautiful resort. We loved every minute. Reviewed on Oct 25, 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/2026-01-21/2026-01-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive 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 $1,102 per person Mar 5 - Mar 8 found 17 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) LOVED this property!! Staff was great and helpful with any questions or concerns we had. Breakfast was fresh and had a variety of selection. Location is super convenient, there was a 24 hr grocery store across the street and walkable to plenty of food & exploration options. Good location for getting around San Juan and to El Yunque. Would stay again! Reviewed on Dec 21, 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 $1,490 per person Mar 5 - Mar 8 found 17 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (328 reviews) The roooooommmm! The room is EVERYTHING! The staff is amazing. The rooftop restaurant has great food. But the room just took it over the top. I absolutely love this hotel. Will definitely be staying here again when I return Reviewed on Dec 17, 2025 ![The Condado Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/7200/7143/e18049f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Condado Plaza Hotel Condado CA $1,168 per person Jan 23 - Jan 26 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8/10 Very Good! (1,814 reviews) Very clean, no issues, easy check in. Reviewed on Dec 19, 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/2026-01-21/2026-01-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![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 $717 per person Feb 23 - Feb 27 found 22 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (500 reviews) The room was clean and the staff polite but it wasn’t luxury. First off, we messaged the hotel a few days in advance for a late check and when I messaged on check in day I was told the hotel was full and that we couldn’t. Also, we booked the penthouse which seemed ok until you learn the restaurant is right next to your room and the restaurant thinks it’s a night club. Or when the fire alarm goes off from the kitchen smoke. It’s a shame because the people are nice and the location is good so we gave 3 stars for that Reviewed on Dec 20, 2025 ![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 $1,558 per person Mar 12 - Mar 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (589 reviews) LOVED this property!! Staff was great and helpful with any questions or concerns we had. Breakfast was fresh and had a variety of selection. Location is super convenient, there was a 24 hr grocery store across the street and walkable to plenty of food & exploration options. Good location for getting around San Juan and to El Yunque. Would stay again! Reviewed on Dec 21, 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 $1,729 per person Mar 13 - Mar 17 found 15 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8.6/10 Excellent! (577 reviews) Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again. Reviewed on Dec 6, 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/2026-01-21/2026-01-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Embark on an unforgettable all-inclusive trip to Roosevelt Roads including airfare with Expedia #### What are some benefits of booking an all-inclusive vacation? When you opt for an all-inclusive vacation to Roosevelt Roads, you can have everything you want to do planned out in advance. That means you get to simply coast through your vacation knowing exactly what's coming next. Plus, this helps you get a final tally on the costs beforehand, so it's much easier on your budget. #### Can I book all-inclusive packages with airfare and meals? Yes, all-inclusive vacation packages are readily available for Roosevelt Roads, and you can search for them simply by using the search filter for all-inclusivity. When you book your flight along with your accommodations, you may even find some savings, with the potential to save up to 43\. #### Why should I book Roosevelt Roads vacations that are all inclusive and adults only? Adults-only stays in Roosevelt Roads are good for travellers who are looking to relax in laid-back and easygoing surroundings. Everyone in the area will be looking to do much of the same without any kids to worry about, so you can truly take in some time for yourself in pampered bliss. Plus, you can filter for adults-only stays specifically in your search, so they're easy to find. #### Can I book all-inclusive packages? Yes, all-inclusive packages are fairly standard in Roosevelt Roads. You can easily find all-inclusive options by using the search filters, but that's just the beginning. If you're booking at the last minute, you may even find additional discounts as properties try to fill their last remaining spots for cheap vacations that are all inclusive. #### Can I book cheap all-inclusive trips to Roosevelt Roads? If you're looking to save, you'll find a wide range of prices available, ranging from CA $717\. By booking your accommodations and flight together, you may be able to enjoy savings of up to 43\. Be sure to sort your search results by price to list the cheapest options first. #### What should I look for when booking a 5-star all-inclusive vacation in Roosevelt Roads? If you've implemented the 5-star filter when searching for your all-inclusive vacation in Roosevelt Roads, there are a few factors to keep an eye out for. Spa access is particularly popular, as it's one of the best features you'll find in luxury accommodation options. Additionally, you should consider opting for an infinity pool and a luxury suite, especially if you're travelling with a relatively large group. #### What should I consider when booking Roosevelt Roads vacation packages that are all inclusive for the family? The most important thing to consider for all-inclusive family vacations to Roosevelt Roads is what your family is interested in. If your kids need access to a pool, you'll want to implement the search filter for that amenity. Kids' clubs can also be perfect for your family, as can babysitting services if the adults in your group plan on enjoying Roosevelt Roads's nightlife. #### How can I find the best deals on all-inclusive vacations in Roosevelt Roads? You can always sort your search results by price to automatically put the cheapest options at the top of your search while still considering all your implemented search filters. #### Can I book an all-inclusive package that is fully refundable? Yes, reservations that are fully refundable are available on some all-inclusive packages in . You can explore each package's cancellation policy in the policy section of their page, where you'll learn exactly how you can qualify. Sometimes, nothing is required to qualify. #### Why should I book an all-inclusive vacation with Expedia? Booking with Expedia makes it easy to find the ultimate all-inclusive vacation package. By offering accommodations and flights together, all-inclusive packages are easy for us to create and for you to enjoy. With benefits like being fully refundable and flexible dates on some packages, you can enjoy a more stree-free booking process. Expedia Rewards members can take that even further with the possibility of additional discounts. ## 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) ### Top All inclusive Vacation Destinations > - 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[All inclusive vacations in the Dominican Republic ](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic) ## 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