Title: Roosevelt Roads Vacation Packages & Trips 2026 from CA $638 | 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)

![](https://images.trvl-media.com/place/6360451/3441fe46-31f2-46bc-b307-613f9edf876d.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Roosevelt Roads Vacation Packages

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

Photo by Shannon Willitts 

- ##  
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Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
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## Top Roosevelt Roads Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Lazy Parrot Inn](https://images.trvl-media.com/lodging/1000000/910000/900400/900306/77384e02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lazy Parrot Inn

CA $638

per person

Mar 1 - Mar 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (1,000 reviews)

Very Clean and equipped.

Reviewed on Jan 5, 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 $1,438

per person

Apr 2 - Apr 9

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

The room is HUGE. Great location! Breakfast was delicious. Wonderful stay

Reviewed on Jan 10, 2026

![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 $3,206

per person

Feb 27 - Mar 6

found 21 hours ago

Roundtrip flight included

Montreal (YUL) to San Juan (SJU)

10/10 Exceptional! (1 review)

Space, location, private accommodations, modern kitchen, washer dryer

Reviewed on Nov 27, 2025

![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 $1,453

per person

Mar 23 - Mar 28

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to San Juan (SJU)

9/10 Wonderful! (500 reviews)

Hector, the receptionist was awesome. Referred us to restaurants and went out of his way to find some friends a room when their Airbnb was canceled. The apartment is nice and spacious. We had a great day.

Reviewed on Jan 10, 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 $2,313

per person

Feb 22 - Feb 28

found 22 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to San Juan (SJU)

9/10 Wonderful! (645 reviews)

We had a great stay at O:live boutique hotel. I’m sorry we didn’t have more time to explore the restaurant, pool, etc but this was a one night stay pre-cruise and we already had dinner reservations off-property. Check in was quick and efficient, the front desk staff was very pleasant. The lobby is cozy and intimate - as is the whole hotel. Our room 203 was a nice surprise - it had a big private courtyard with lounge seating, cafe table and chairs, and a really cool outdoor tub/shower. The bedding was very comfortable, the bathroom clean and modern. I would definitely stay here again and I would set aside some time to experience the pool, restaurant, etc.

Reviewed on Jan 10, 2026

## Ready to book your vacation to Roosevelt Roads?

Choose your dates

## Roosevelt Roads Hotel Deals

![Hyatt Regency Grand Reserve Puerto Rico](https://images.trvl-media.com/lodging/1000000/980000/979700/979694/08d6d09c_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 $626

CA $805 total

Jan 20 - Jan 21

includes taxes & fees

8.8/10 Excellent! (2,860 reviews)

The stay was very enjoyable. Able to relax and enjoy the amenities. Service was good, everyone was friendly

Reviewed on Jan 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=20%2F01%2F2026&endDate=21%2F01%2F2026&selected=979694&PinnedHotelID=979694&HadPinnedHotel=true&regionId=6360451)

![El Conquistador Resort](https://images.trvl-media.com/lodging/1000000/450000/447600/447559/926a31f3_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

El Conquistador Resort

1000 Conquistador Avenue Fajardo 

Fully refundableReserve now, pay when you stay

CA $437

CA $575 total

Jan 15 - Jan 16

includes taxes & fees

9/10 Wonderful! (3,202 reviews)

Very clean. Excellent staff. We love it

Reviewed on Jan 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F01%2F2026&endDate=16%2F01%2F2026&selected=447559&PinnedHotelID=447559&HadPinnedHotel=true&regionId=6360451)

![Wyndham Grand Rio Mar Rainforest Beach and Golf Resort](https://images.trvl-media.com/lodging/1000000/50000/41700/41642/0558d37f_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 $877

CA $1,206 total

Feb 5 - Feb 6

includes taxes & fees

8.4/10 Very Good! (2,274 reviews)

Clean room, good service

Reviewed on Jan 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=41642&PinnedHotelID=41642&HadPinnedHotel=true&regionId=6360451)

[See all 2,076 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F01%2F2026&endDate=13%2F01%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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