Title: Luxury 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 Luxury 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 Luxury 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/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,534 per person May 1 - May 7 found 2 days ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 8.8/10 Excellent! (594 reviews) Room had ample space, bed was very comfortable, appreciated the 24/7 access to coffee and filtered water. Staff was super friendly Reviewed on Mar 25, 2026 ![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 $1,871 per person Jun 15 - Jun 21 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (741 reviews) Breakfast was good and fresh Reviewed on Mar 27, 2026 ![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 $1,829 per person May 1 - May 7 found 2 days ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9.2/10 Wonderful! (469 reviews) Great beach place. Walk right out to beach. Waited service on beach. Staff opens the door for you. Foods good. What else do you need?… Reviewed on Mar 22, 2026 ![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 $2,095 per person May 1 - May 7 found 2 days ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 9/10 Wonderful! (662 reviews) The noise is unbearable. We were on the third floor and had small windows connected a metal stairway that is so loud and it was like they were having a party up on the roof all night. We had to be up at 1am to catch a flight and couldn’t sleep at all. Between the paper thin walls where we hear everything the other rooms in our hall were doing and the loud party, we couldn’t sleep. At $500 a night this was unacceptable. The place is clean and comfortable, but you can’t relax at night with all the noise. Reviewed on Mar 9, 2026 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/4da8a2f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $1,943 per person May 1 - May 7 found 2 days ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 8.6/10 Excellent! (622 reviews) The pool and upstairs lounge area was great, but the rooms did not match the cost. They need to replace several fixtures in the bedroom but the balcony view was nice this felt like a 3-star but charged 4 star prices. Reviewed on Mar 16, 2026 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/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Fairmont El San Juan Hotel](https://images.trvl-media.com/lodging/1000000/10000/1600/1592/863801f3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont El San Juan Hotel Isla Verde CA $1,999 per person Jun 2 - Jun 9 found 7 hours ago Roundtrip non-stop flight included Montreal (YUL) to San Juan (SJU) 8.6/10 Excellent! (2,069 reviews) Pool and beach were awesome. Staff overall was average. Some were nice & friendly while others hospitality skills were lacking. Resort is beautiful. Reviewed on Mar 27, 2026 ![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 $2,760 per person Jun 15 - Jun 21 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to San Juan (SJU) 7.6/10 Good! (138 reviews) The beach was nice but the lounge chair cushions were filthy …. The casino customer service was mediocre Reviewed on Mar 24, 2026 ![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 $2,447 per person Jun 14 - Jun 21 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.4/10 Exceptional! (1,702 reviews) We had a great stay here. Great room and pool area. Reviewed on Mar 26, 2026 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/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,379 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8.8/10 Excellent! (594 reviews) Room had ample space, bed was very comfortable, appreciated the 24/7 access to coffee and filtered water. Staff was super friendly Reviewed on Mar 25, 2026 ![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 $1,629 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 9.2/10 Wonderful! (469 reviews) Great beach place. Walk right out to beach. Waited service on beach. Staff opens the door for you. Foods good. What else do you need?… Reviewed on Mar 22, 2026 ![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/4da8a2f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OLV Fifty Five - Adults Only Condado CA $1,635 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to San Juan (SJU) 8.6/10 Excellent! (622 reviews) The pool and upstairs lounge area was great, but the rooms did not match the cost. They need to replace several fixtures in the bedroom but the balcony view was nice this felt like a 3-star but charged 4 star prices. Reviewed on Mar 16, 2026 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/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Roosevelt Roads Price found within the past 48 hours. Click for updated prices. ![Lazy Parrot Inn](https://images.trvl-media.com/lodging/1000000/910000/900400/900306/d84e57b2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lazy Parrot Inn CA $1,073 per person Jun 14 - Jun 18 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9.2/10 Wonderful! (1,007 reviews) Loved this room. Clean and comfortable- quiet yet accessible. Highly recommend. Reviewed on Mar 23, 2026 ![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Puerto Valdes San Juan Antiguo CA $1,232 per person May 27 - May 31 found 2 hours ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 8.8/10 Excellent! (594 reviews) Room had ample space, bed was very comfortable, appreciated the 24/7 access to coffee and filtered water. Staff was super friendly Reviewed on Mar 25, 2026 ![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 $1,204 per person Jun 14 - Jun 18 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to San Juan (SJU) 9/10 Wonderful! (741 reviews) Breakfast was good and fresh Reviewed on Mar 27, 2026 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/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury Roosevelt Roads vacation with Expedia #### What are some benefits when booking luxury Roosevelt Roads vacations? When you book a luxury Roosevelt Roads vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. #### How can I find all-inclusive luxury vacations in Roosevelt Roads? If you're looking for something luxurious in Roosevelt Roads, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. #### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,073, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 40\. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. #### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in Roosevelt Roads. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. #### What should I look for in a luxury family vacation in Roosevelt Roads? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Roosevelt Roads. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in Roosevelt Roads. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. #### What can help me find the best luxury vacation deals in Roosevelt Roads? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Roosevelt Roads or travelling to more obscure destinations altogether can often lead to lower prices. #### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in Roosevelt Roads. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. #### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## 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 Luxury Vacation Destinations > - [Luxury vacations in India ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## 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