Title: Roosevelt Roads Vacation Packages & Trips 2026 from CA $718 | 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 $718

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 6 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Staff was awesome, room was clean. Breakfast was the same every day, omelette, sausage/hot dogs, yogurt, strong coffee, and juice. Outside of the building didn’t match photos on website or Expedia. There were no amenities, rooftop was closed, no spa, no hot tub. Great access to everything in San Juan. No restaurant on site, no laundry, not in a nature reserve it’s in the middle of San Juan. No sauna, no banquet hall, elevator was questionable. For the price it was a great stay, but if you need a hot tub or spa you’ll have to drive. Check in wasn’t on time, but we got a similar room after waiting a few hours. No golf course nearby! We really enjoyed our stay water pressure and temperature was awesome!

Reviewed on Jan 3, 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 4 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

![The Oliver Hotel](https://images.trvl-media.com/lodging/108000000/107090000/107083400/107083384/2b5683ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Oliver Hotel

San Juan Antiguo

CA $1,417

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to San Juan (SJU)

9/10 Wonderful! (50 reviews)

Definitely a different experience to not have a ton of amenities or staff on site at all times as they manage multiple properties. That being said, they were always a quick text or phone call away and everyone was extremely friendly and helpful. Great location and very clean room. I would definitely recommend this spot for the next traveler looking for a great (and walkable) place to stay near Old San Juan and/or Condado.

Reviewed on Jan 5, 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 $2,557

per person

Mar 18 - Mar 24

found 1 day ago

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

## 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 $648

CA $834 total

Jan 14 - Jan 15

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=14%2F01%2F2026&endDate=15%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 $873

CA $1,202 total

Feb 6 - Feb 7

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=06%2F02%2F2026&endDate=07%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=11%2F01%2F2026&endDate=12%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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