Title: Pet-friendly 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 Pet-friendly Vacations

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## Flight and Pet-friendly hotel deals 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 $802

per person

Jan 25 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (500 reviews)

Really nice apartment with a great view, we could live there. 5-10 minute walk to old town shops and restaurants, as well as cruise terminal.

Reviewed on Dec 8, 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 $936

per person

Jan 25 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

The overall stay was amazing . Quick check in and out . What concerned me was 1\. The room we had booked wasn’t exactly what we got. Not saying it was a huge issue , but a small clarification into why we getting a different room than what was booked 2\. Cleanliness was not top tier . I do highly appreciate the bed being made as we were all out but that’s about it . The floor remained the same with our hair from our flat irons and etc . Also having to go back downstairs to get more towels and a rug for the bathroom was a tad bit frustrating. Overall .. it’s a beautiful hotel . Nice and quiet

Reviewed on Dec 12, 2025

![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 $1,466

per person

Jan 25 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (328 reviews)

Staff was very friendly and helpful. Beach access was great. However the phone in the room did not work.

Reviewed on Dec 11, 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 $1,493

per person

Jan 25 - Jan 30

found 1 day ago

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

![Hyatt Regency Grand Reserve Puerto Rico](https://images.trvl-media.com/lodging/1000000/980000/979700/979694/08d6d09c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Regency Grand Reserve Puerto Rico

Zarzal

CA $1,406

per person

Jan 25 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (2,764 reviews)

Very clean room and helpful staff!

Reviewed on Dec 12, 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/2026-01-13/2026-01-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Pet-friendly 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 $1,667

per person

Jan 25 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (1,616 reviews)

One of the best of San Juan!!!!!

Reviewed on Dec 12, 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 $3,855

per person

Feb 15 - Feb 21

found 21 hours ago

Roundtrip flight included

Montreal (YUL) 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

![Fairmont El San Juan Hotel](https://images.trvl-media.com/lodging/1000000/10000/1600/1592/99d8d575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Fairmont El San Juan Hotel

Isla Verde

CA $1,957

per person

Jan 25 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.4/10 Very Good! (2,051 reviews)

We had a wonderful stay and will book again to spend more time in the next stay. Great location and great beach access along with pools, gym and bilingual staff.

Reviewed on Dec 13, 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/2026-01-13/2026-01-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Pet-friendly holidays in Roosevelt Roads

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

![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 $1,944

per person

Feb 13 - Feb 16

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

9/10 Wonderful! (328 reviews)

Staff was very friendly and helpful. Beach access was great. However the phone in the room did not work.

Reviewed on Dec 11, 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 $1,959

per person

Feb 13 - Feb 16

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) 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

![MARU by DW](https://images.trvl-media.com/lodging/113000000/112180000/112174900/112174847/60d84c71_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### MARU by DW

Condado

CA $1,993

per person

Feb 13 - Feb 16

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

9.2/10 Wonderful! (15 reviews)

Supermarket near by a late night bite truck near by was very convenient neighborhood safe

Reviewed on Oct 28, 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/2026-01-13/2026-01-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Pet-friendly 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 $967

per person

Feb 16 - Feb 20

just found

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (50 reviews)

Hotel was quit ,and clean on arrival but you need to ask to clean the room, asked for towels and cream for coffee. Got the towels an hour later never got cream . No one at front desk, need to call for assistance

Reviewed on Dec 8, 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 $1,067

per person

Feb 16 - Feb 20

just found

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

The overall stay was amazing . Quick check in and out . What concerned me was 1\. The room we had booked wasn’t exactly what we got. Not saying it was a huge issue , but a small clarification into why we getting a different room than what was booked 2\. Cleanliness was not top tier . I do highly appreciate the bed being made as we were all out but that’s about it . The floor remained the same with our hair from our flat irons and etc . Also having to go back downstairs to get more towels and a rug for the bathroom was a tad bit frustrating. Overall .. it’s a beautiful hotel . Nice and quiet

Reviewed on Dec 12, 2025

![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 $1,410

per person

Feb 16 - Feb 20

just found

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (328 reviews)

Staff was very friendly and helpful. Beach access was great. However the phone in the room did not work.

Reviewed on Dec 11, 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/2026-01-13/2026-01-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=SJU&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Pet-friendly Hotels in Roosevelt Roads

![Mami Ana Beach House.10min ferry Vieques/Culebra. Beautifull, excelent location](https://images.trvl-media.com/lodging/117000000/116230000/116226000/116225958/w905h683x59y0-5f02425f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Mami Ana Beach House.10min ferry Vieques/Culebra. Beautifull, excelent location

 Ceiba Puerto rico

- 9 min drive from Ceiba Ferry Terminal

Book a stay at this beach villa in Ceiba. Enjoy a beach locale, an in-room coffeemaker, and air conditioning. Popular attractions Ceiba Ferry Terminal and El ...

2/10 (1 review)

To start you have to park a distance away and transport all your things across a makeshift bridge that is leaning to one side. You have to beal with roosters all over the place. The kitchen is in main level with minimal amenities and no ac.The upstairs was ok but the ac can only ho down to 70 and ...

Reviewed on Aug 4, 2025

[](https://expedia.ca/Ceiba-Hotels-Mami-Ana-Beach-House10min-Ferry-ViequesCulebra-Beautifull.h116225958.Hotel-Information)

[See all 2,107 properties in Roosevelt Roads](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&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.

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[Flights to Roosevelt Roads

](https://expedia.ca/Cheap-Flights-To-Roosevelt-Roads.d6360451.Travel-Guide-Flights)[

Roosevelt Roads Hotels

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Roosevelt Roads Vacation Rentals

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Roosevelt Roads Car Rentals

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