Title: All inclusive 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 All inclusive 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 All inclusive hotel deals in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Romeo Gay Hotel](https://images.trvl-media.com/lodging/105000000/104580000/104571300/104571256/c3574a90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Romeo Gay Hotel San Juan Antiguo CA $1,234 per person Jan 8 - Jan 15 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to San Juan (SJU) 9/10 Wonderful! (100 reviews) The property is perfect to couples and relaxing days Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-15/?FromAirport=YHM&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104571256&paandie=true&HotelClass=40&dealMarker=nXxKQN86CE5GVUah-AZkOkfm3vWq8pbK1uwfr5jXFUQ4V8sTjFSlQfex18BQCYBX) ![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 $1,638 per person Jan 8 - Jan 15 found 1 day ago Roundtrip non-stop 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/2026-01-08/2026-01-15/?FromAirport=YHM&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&HotelClass=40&dealMarker=k361K6qHdSeaxaRnh0KGlUBM6MNWtR0HxYK1rtlIco7hl7VvvryaUCntbNqanCFY) ![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 $2,092 per person Jan 8 - Jan 15 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to San Juan (SJU) 9/10 Wonderful! (290 reviews) Lovely hotel &services Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-15/?FromAirport=YHM&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=527599&paandie=true&HotelClass=40&dealMarker=nXxKQN86CE5GVUah-AZkOrvHllRbq_FiwUe1xzS9IqfkfPno0UZ1HjEZlJJcNmsx) ![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 $2,175 per person Jan 9 - Jan 16 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) 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/2026-01-09/2026-01-16/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5196263&paandie=true&HotelClass=40&dealMarker=OYZjp4K4FCHo9jEFTVVIkojhSgU88Z2vBUnCEw5o6jTbWQ-NwPF-CDfg2Tvf0wcT) ![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 $2,432 per person Jan 4 - Jan 11 found 6 hours ago Roundtrip 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/2026-01-04/2026-01-11/?FromAirport=YUL&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23155605&paandie=true&HotelClass=40&dealMarker=nfOcTDgRHwg5SXuwSNlv9PR-7jbIPDyD70tzb7_sEUjVRKo6zQBHNLIO25DbFeZv) 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/2025-11-23/2025-11-30/?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 $1,664 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (1,602 reviews) Amazing and kind staff , breathtaking pool , great location Reviewed on Oct 21, 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=9105241&paandie=true&HotelClass=50&dealMarker=Yz0FwWILdLN1BHM2sIaeGvIvZlc3LWIsOmm3Ev2SDjlAlxrWXTNAD8ocx7Hf29US) ![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 $1,963 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.4/10 Very Good! (2,018 reviews) Everything excellent Reviewed on Oct 22, 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=1592&paandie=true&HotelClass=50&dealMarker=Yz0FwWILdLN1BHM2sIaeGvIvZlc3LWIsOmm3Ev2SDjmzayXHesix1Q8DaDzlLOGz) ![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 $32,472 per person Jan 9 - Jan 16 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 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6668065&paandie=true&HotelClass=50&dealMarker=VQOyAN7p_xUUaMfVEk5jc5DSgMDJ_2s6ppuL5njA3unC9duZgZGftMExbFI7N60S) 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/2025-11-23/2025-11-30/?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. ![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 $830 per person Dec 11 - Dec 14 found 11 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (12 reviews) Mary property was simply gorgeous. The ambience is amazing. The beautiful showers located inside and outside are just to die for. Great for a couples retreat. There is a 24 hour grocery with affordable prices just one block away. The party area La Placita is just a 6 min Uber ride away and only costs 8 bucks or less. The beach is a few blocks away but easily walkable. My partner and I love this space and area. We will definitely return and recommend. Thanks for letting us stay. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-11/2025-12-14/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=112174847&paandie=true&HotelClass=40&dealMarker=hEcxEAl0cQr8TKY7Kq7rzh2vqyBXiGXc9AWF3ENZwfsvQJdiiTZyi4gjCfbLfF48) ![Romeo Gay Hotel](https://images.trvl-media.com/lodging/105000000/104580000/104571300/104571256/c3574a90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Romeo Gay Hotel San Juan Antiguo CA $1,050 per person Dec 4 - Dec 7 found 1 hour ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9/10 Wonderful! (100 reviews) The property is perfect to couples and relaxing days Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-07/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=104571256&paandie=true&HotelClass=40&dealMarker=gypK47YNEr6o8HBfjoQztVOd3T2iWgHNHYQN90kknlnUYs_RkvE4ck0j9bL0aYFN) ![APT by DW](https://images.trvl-media.com/lodging/92000000/91290000/91280100/91280057/d4050922_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### APT by DW Santurce CA $1,279 per person Dec 5 - Dec 8 found 21 hours ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.8/10 Exceptional! (72 reviews) Loved this property! Owner was so nice and very responsive. Whatever we needed they were able to help us. Would definitely book again. The area is walkable for all Your needs from groceries to restaurants. Reviewed on Jun 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-05/2025-12-08/?FromAirport=YYZ&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=91280057&paandie=true&HotelClass=40&dealMarker=hEcxEAl0cQr8TKY7Kq7rzs1s6h0Go_W3nIzvdrwPRfWuTZy9p3agfLxX-FWGl0VS) 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/2025-11-23/2025-11-30/?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 $1,097 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) 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/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=69371387&paandie=true&dealMarker=QXQ5CKBEfcG08VxKG3nPxx9wBkxD2UuC6h2F6T_zJleUAXZ6I5_3b5lSu2SoYct_) ![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 $1,163 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 10/10 Exceptional! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-02/2025-12-06/?FromAirport=YTO&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&hotelId=116013898&paandie=true&dealMarker=zsdb7AqbqTyQd7e-XzjFS-AZZPthP0HH7ZljJUkc37bKJimQyzATju2HdZDP55aW) ![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 $1,173 per person Dec 2 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (290 reviews) Lovely hotel &services Reviewed on Oct 21, 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=527599&paandie=true&dealMarker=O9iEKakaAYnqtbuvshxqYnVmD7JV_Tu39Kre2LCJn5pnbB1XrCUoGR_do-1EKVle) 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/2025-11-23/2025-11-30/?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 39. #### 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 $830. By booking your accommodations and flight together, you may be able to enjoy savings of up to 39. 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 Sosúa](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/601998/Sosua) > - [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. 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