Title: Roosevelt Roads Vacation Packages & Trips 2026 from CA $1,601 | Expedia.ca

[Roosevelt Roads Travel Guide](https://expedia.ca/Roosevelt-Roads.dx6360451)[Hotels in Roosevelt Roads](https://expedia.ca/Roosevelt-Roads-Hotels.d6360451.Travel-Guide-Hotels)[Vacation Rentals in Roosevelt Roads](https://expedia.ca/Roosevelt-Roads-Vacation-Rentals.d6360451.Travel-Guide-VacationRentals)[Flights to Roosevelt Roads](https://expedia.ca/Cheap-Flights-To-Roosevelt-Roads.d6360451.Travel-Guide-Flights)[Roosevelt Roads Car Rentals](https://expedia.ca/Car-Rentals-In-Roosevelt-Roads.d6360451.Car-Rental-Guide)

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# Roosevelt Roads Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
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Better together  
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## Top Roosevelt Roads Vacation Deals

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 $1,601

per person

Jun 6 - Jun 12

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

8.8/10 Excellent! (594 reviews)

The staff service, and cleanliness and spaciousness of the unit we rented were excellent.

Reviewed on Mar 24, 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 $1,906

per person

Jun 15 - Jun 21

found 18 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

9/10 Wonderful! (741 reviews)

What the website advertised and what we got were two completely different things, it states there was a spa and showed pictures of a beautiful spa setting which was a big reason as to why we stayed there but really there is no spa. The spa is a whole different business and we would have to pay to use it. There are no shower curtains therefore you bathroom ends up completely flooded, fall risk needles to say the breakfast was one maybe a young child would eat, the walls are thin so you can hear the neighbors, parking you have to pay for ontop of the room rental each day tou stay its a fee, the parking area is small and hard to get in and out of. The positive found was the amazing staff member who checked us in and the mere fact we were in Puerto Rico

Reviewed on Mar 23, 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 $1,731

per person

May 1 - May 7

found 1 day 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

![Enjoy our Luxurious Penthouse in Condado](https://images.trvl-media.com/lodging/121000000/120050000/120044800/120044729/b71982f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Enjoy our Luxurious Penthouse in Condado

Santurce

CA $2,812

per person

Jun 10 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

No reviews

![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 $1,752

per person

May 7 - May 12

found 1 day 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

## Ready to book your vacation to Roosevelt Roads?

Choose your dates

## Roosevelt Roads Hotel Deals

![El Conquistador Resort](https://images.trvl-media.com/lodging/1000000/450000/447600/447559/d7e2f092_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

El Conquistador Resort

1000 Conquistador Avenue Fajardo 

CA $457

CA $596 total

Mar 30 - Mar 31

includes taxes & fees

9/10 Wonderful! (3,317 reviews)

I loved the hotel and beach. The perssonal were very polite at all the time. My only disappointment is that I saw two cucarachas in my room

Reviewed on Mar 25, 2026

[](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=447559&PinnedHotelID=447559&HadPinnedHotel=true&regionId=6360451)

![Hyatt Regency Grand Reserve Puerto Rico](https://images.trvl-media.com/lodging/1000000/980000/979700/979694/19acd880_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt Regency Grand Reserve Puerto Rico

200 Coco Beach Blvd. Highway 955-I Río Grande 

Fully refundableReserve now, pay when you stay

CA $508

CA $653 total

Apr 11 - Apr 12

includes taxes & fees

9/10 Wonderful! (2,961 reviews)

Room was updated. clean and quite spacious. Very high ceilings throughout and updated bathroom with a rainfall shower with great water pressure. The grounds were stunning and spread out so nothing felt crowded. We never had an issue getting beach chairs or chairs at the pool in the height of spring ...

Reviewed on Mar 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F04%2F2026&endDate=12%2F04%2F2026&selected=979694&PinnedHotelID=979694&HadPinnedHotel=true&regionId=6360451)

![Wyndham Grand Rio Mar Rainforest Beach and Golf Resort](https://images.trvl-media.com/lodging/1000000/50000/41700/41642/07f69518_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

6000 Rio Mar Boulevard Río Grande 

Fully refundableReserve now, pay when you stay

CA $582

CA $801 total

Mar 27 - Mar 28

includes taxes & fees

8.6/10 Excellent! (2,226 reviews)

Would love to stay again

Reviewed on Mar 25, 2026

[](https://expedia.ca/Hotel-Search?startDate=27%2F03%2F2026&endDate=28%2F03%2F2026&selected=41642&PinnedHotelID=41642&HadPinnedHotel=true&regionId=6360451)

[See all 2,115 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&regionId=6360451)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

![](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)

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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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