Title: Roosevelt Roads Vacation Packages & Trips 2026 from CA $873 | 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://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Roosevelt Roads Vacation Packages

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

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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 $873

per person

Mar 18 - Mar 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (1,000 reviews)

Great room with view of the property and sunset. The Thai restaurant was fantastic! The property was very well managed, cared for and cleaned, the grounds keeper does an amazing job. The clean pool and hot tub were winderful ways to end your day in Rincon. We'll be back!

Reviewed on Jan 11, 2026

![Mata e' Platano Guesthouse](https://images.trvl-media.com/lodging/107000000/106070000/106061900/106061892/a720b844_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Mata e' Platano Guesthouse

Mata de Plátano

CA $2,236

per person

Feb 19 - Feb 26

found 16 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to San Juan (SJU)

8.8/10 Excellent! (103 reviews)

We believe it would benefit you to have a little variety for your breakfast. Would also suggest you have a small shelf area in the breakfast room where you put towels so people can swap them out every few days. The shower in Unit six has water coming out of the drain so it doesn't all come out the shower head. The water was never very hot but it was warm. Even with these issues we would stay there again because the staff was so nice.

Reviewed on Jan 9, 2026

![Placid Suites](https://images.trvl-media.com/lodging/31000000/30040000/30037000/30036979/9696d4e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Placid Suites

Condado

CA $1,055

per person

Mar 7 - Mar 14

found 2 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to San Juan (SJU)

8/10 Very Good! (1,002 reviews)

A convenient location near everything.

Reviewed on Jan 15, 2026

![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 $1,157

per person

Mar 18 - Mar 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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

![Ocean Breeze Villa](https://images.trvl-media.com/lodging/122000000/121510000/121501200/121501175/771233e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ocean Breeze Villa

San Juan Antiguo

CA $1,538

per person

Mar 7 - Mar 14

found 2 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to San Juan (SJU)

No reviews

## 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 $360

CA $463 total

Feb 1 - Feb 2

includes taxes & fees

9/10 Wonderful! (2,880 reviews)

The amenities were one of the best ones for a luxury resort, the staff were very hospitable. Rooms were clean and with modern furniture and design.

Reviewed on Jan 12, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%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 $436

CA $574 total

Jan 27 - Jan 28

includes taxes & fees

9/10 Wonderful! (3,215 reviews)

Everything was perfect. Really nice staff and the island was amazing

Reviewed on Jan 14, 2026

[](https://expedia.ca/Hotel-Search?startDate=27%2F01%2F2026&endDate=28%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 

CA $750

CA $1,054 total

Feb 7 - Feb 8

includes taxes & fees

8.4/10 Very Good! (2,269 reviews)

Very nice stay. Great staff. Quite expensive.

Reviewed on Jan 12, 2026

[](https://expedia.ca/Hotel-Search?startDate=07%2F02%2F2026&endDate=08%2F02%2F2026&selected=41642&PinnedHotelID=41642&HadPinnedHotel=true&regionId=6360451)

[See all 2,180 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F01%2F2026&endDate=18%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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