Title: Adventure 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 Adventure Vacations

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## Flight and Adventure hotel deals in Roosevelt Roads

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

![Romeo Gay Hotel](https://images.trvl-media.com/lodging/105000000/104580000/104571300/104571256/c3574a90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Romeo Gay Hotel

San Juan Antiguo

CA $1,163

per person

Feb 22 - Mar 1

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to San Juan (SJU)

9/10 Wonderful! (121 reviews)

Super convenient location, bar across the street, convenience store and liquor across the street The bar “5” across the street has pool table and Jenna games, super cool. All entrances with gate security codes, common area to work and leave suitcase before and after check in/out Very close to port and old San Juan. Isla verde and condado 10 minute drive ( if that far) We had an amazing time. We travel with family

Reviewed on Dec 6, 2025

![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 $1,358

per person

Feb 22 - Mar 1

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Clean roon staff friendly and professional

Reviewed on Dec 15, 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 $1,727

per person

Feb 15 - Feb 22

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to San Juan (SJU)

9/10 Wonderful! (500 reviews)

The hotel was really cute but our room was not thoroughly cleaned. Table had grease stain and crumbs. Mucus in sink and toilet not clean. We were too tired to go down and say something.

Reviewed on Dec 14, 2025

![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/29ce7de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### OLV Fifty Five - Adults Only

Condado

CA $2,275

per person

Feb 4 - Feb 11

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

8.6/10 Excellent! (577 reviews)

Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again.

Reviewed on Dec 6, 2025

![Las Casitas Village at El Conquistador](https://images.trvl-media.com/lodging/92000000/91570000/91562100/91562080/7e550371_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Las Casitas Village at El Conquistador

Cabezas

CA $3,533

per person

Mar 8 - Mar 14

found 5 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

9.2/10 Wonderful! (126 reviews)

Everything was great

Reviewed on Dec 4, 2025

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/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Adventure holidays in Roosevelt Roads

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

![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 $2,561

per person

Feb 4 - Feb 11

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

9.2/10 Wonderful! (1,616 reviews)

Room, staff, service, ambiance, location were perfect! I'll be back!

Reviewed on Dec 14, 2025

![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 $4,080

per person

Feb 15 - Feb 22

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to San Juan (SJU)

7.6/10 Good! (128 reviews)

Bianca and Melanie at the front desk were both very helpful and accommodating.

Reviewed on Sep 28, 2025

![The St. Regis Bahia Beach Resort, Puerto Rico](https://images.trvl-media.com/lodging/4000000/3810000/3800200/3800119/f088cdb4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The St. Regis Bahia Beach Resort, Puerto Rico

Herreras

CA $7,188

per person

Mar 8 - Mar 14

found 5 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

9.4/10 Exceptional! (450 reviews)

Beautiful resort. We loved every minute.

Reviewed on Oct 25, 2025

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/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Adventure holidays in Roosevelt Roads

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

![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/0dc1a939_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Puerto Valdes

San Juan Antiguo

CA $633

per person

Mar 8 - Mar 11

found 7 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

9/10 Wonderful! (500 reviews)

The hotel was really cute but our room was not thoroughly cleaned. Table had grease stain and crumbs. Mucus in sink and toilet not clean. We were too tired to go down and say something.

Reviewed on Dec 14, 2025

![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 $782

per person

Feb 16 - Feb 19

just found

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Clean roon staff friendly and professional

Reviewed on Dec 15, 2025

![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/29ce7de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### OLV Fifty Five - Adults Only

Condado

CA $1,152

per person

Feb 16 - Feb 19

just found

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.6/10 Excellent! (577 reviews)

Very beautiful place . Classy and sexy environment . I LOVED the room with the barn door I felt rich or something and don’t get me started on the shower in there. I could not get my man out of there he loves the amenities so much LOL. Def in a good location close to shopping areas and the strip . I would def book again.

Reviewed on Dec 6, 2025

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/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Adventure holidays in Roosevelt Roads

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

![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 $889

per person

Mar 7 - Mar 11

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (50 reviews)

Nothing really close by, no front staff ever on site to help with local restaurants etc no stores nearby have to Uber everywhere. Rooms have no windows no water , ice machines etc..

Reviewed on Dec 14, 2025

![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 $1,063

per person

Feb 16 - Feb 20

found 22 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Clean roon staff friendly and professional

Reviewed on Dec 15, 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 $983

per person

Jan 24 - Jan 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

9/10 Wonderful! (500 reviews)

The hotel was really cute but our room was not thoroughly cleaned. Table had grease stain and crumbs. Mucus in sink and toilet not clean. We were too tired to go down and say something.

Reviewed on Dec 14, 2025

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/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

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## 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)

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