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/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Puerto Valdes

San Juan Antiguo

CA $1,055

per person

May 4 - May 9

found 11 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to San Juan (SJU)

8.8/10 Excellent! (594 reviews)

The staff here were very friendly and helping whenever needed. Best part is how close it is to San Juan. The neighborhood it's in can be sketch for some people, but try to believe me, you are good. The condition of the room could've been better. Spots on the couch, unkept rug, floor tiles lifting, ceiling peeling. None of it was eggrecious to a point we didn't feel comfortable, but more so details missed that can be improved. You also don't have a view out to anytign but an empty lot with graffiti on an abandoned building. BUT if you're looking for somewhere to simply sleep and change clothes, this is perfect. Lol honestly it's a very ok, 3/5, 5-6/10 place. You'll only be disappointed thinking you're staying at a Marriott. BRING YOUR OWN WASH CLOTHS AND TOWELS. Lol they run out fast.

Reviewed on Mar 19, 2026

![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 $1,546

per person

Jun 1 - Jun 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to San Juan (SJU)

9.2/10 Wonderful! (469 reviews)

We stayed a week and had a wonderful experience. The hotel is located near everything you need and the beach view was memorable. The shower! The shower! The shower! We have been trying to figure out how to make our shower at home, like the hotel shower.

Reviewed on Mar 20, 2026

![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/4da8a2f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### OLV Fifty Five - Adults Only

Condado

CA $2,133

per person

May 4 - May 9

found 4 hours ago

Roundtrip flight included

Hamilton (YHM) to San Juan (SJU)

8.6/10 Excellent! (622 reviews)

The pool and upstairs lounge area was great, but the rooms did not match the cost. They need to replace several fixtures in the bedroom but the balcony view was nice this felt like a 3-star but charged 4 star prices.

Reviewed on Mar 16, 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 $1,993

per person

Apr 23 - Apr 26

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

9/10 Wonderful! (662 reviews)

The noise is unbearable. We were on the third floor and had small windows connected a metal stairway that is so loud and it was like they were having a party up on the roof all night. We had to be up at 1am to catch a flight and couldn’t sleep at all. Between the paper thin walls where we hear everything the other rooms in our hall were doing and the loud party, we couldn’t sleep. At $500 a night this was unacceptable. The place is clean and comfortable, but you can’t relax at night with all the noise.

Reviewed on Mar 9, 2026

![DUNA by DW](https://images.trvl-media.com/lodging/79000000/78740000/78739700/78739626/74df8840_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### DUNA by DW

Santurce

CA $1,697

per person

May 22 - May 27

found 7 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.4/10 Exceptional! (76 reviews)

We stayed in the Romance Room at Duna by DW and overall had a wonderful experience. The room was nicely sized, well-ventilated, and decorated with a beautiful rustic tropical style. It was also very clean and comfortable, which made our stay especially enjoyable. One small drawback was the bathroom door—it’s an older sliding door that was very loud and could definitely use an upgrade. The room could also benefit from additional hangers and drawers so guests have more space to unpack their clothing. Customer service was excellent. We had minor issues with the TV and hot water, and both were addressed immediately. The responsiveness of the staff was greatly appreciated. One suggestion would be to include room cleaning during the stay—it would be a nice added touch. The location felt very safe and is close to a scenic, clean beach. It’s also within easy walking distance of several great restaurants, which was very convenient. Overall, we really enjoyed our stay and would recommend Duna by DW. It

Reviewed on Mar 11, 2026

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/2026-04-21/2026-04-28/?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.

![Fairmont El San Juan Hotel](https://images.trvl-media.com/lodging/1000000/10000/1600/1592/863801f3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Fairmont El San Juan Hotel

Isla Verde

CA $1,531

per person

Jun 14 - Jun 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.6/10 Excellent! (2,069 reviews)

The service at the beach was atrocious.

Reviewed on Mar 17, 2026

![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 $2,832

per person

Apr 26 - May 2

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to San Juan (SJU)

7.6/10 Good! (138 reviews)

Room was good but dated, toilet wouldn't stop running.. asked front dest to sweep my patio and get rid of some ants as well as clean cat hair off my lounge chair on Saturday, never seen anyone and i left on Tuesday

Reviewed on Feb 26, 2026

![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 $2,577

per person

May 4 - May 9

found 4 hours ago

Roundtrip flight included

Hamilton (YHM) to San Juan (SJU)

9.4/10 Exceptional! (1,702 reviews)

A little pricey but excellent hotel and service. The actual beach is really small, which was a little disappointing based on the pictures i had seen. Had to wait almost an hour after check in time (4PM) and had already been waiting for over an hour, but lots of people were also on the same boat.

Reviewed on Mar 19, 2026

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/2026-04-21/2026-04-28/?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.

![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 $1,263

per person

Jun 3 - Jun 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to San Juan (SJU)

9/10 Wonderful! (741 reviews)

The spa is actually across the street and not in the building, the staff are lovely! I didn’t have a wash cloth my first night but who is washing with rags anyway? Other than that, no complaints.

Reviewed on Mar 18, 2026

![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 $1,817

per person

Apr 23 - Apr 26

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

9.2/10 Wonderful! (469 reviews)

We stayed a week and had a wonderful experience. The hotel is located near everything you need and the beach view was memorable. The shower! The shower! The shower! We have been trying to figure out how to make our shower at home, like the hotel shower.

Reviewed on Mar 20, 2026

![OLV Fifty Five - Adults Only](https://images.trvl-media.com/lodging/24000000/23160000/23155700/23155605/4da8a2f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### OLV Fifty Five - Adults Only

Condado

CA $1,658

per person

May 22 - May 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.6/10 Excellent! (622 reviews)

The pool and upstairs lounge area was great, but the rooms did not match the cost. They need to replace several fixtures in the bedroom but the balcony view was nice this felt like a 3-star but charged 4 star prices.

Reviewed on Mar 16, 2026

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/2026-04-21/2026-04-28/?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.

![Hotel Puerto Valdes](https://images.trvl-media.com/lodging/70000000/69380000/69371400/69371387/95ad4f15_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Puerto Valdes

San Juan Antiguo

CA $1,064

per person

May 11 - May 15

found 10 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

8.8/10 Excellent! (594 reviews)

The staff here were very friendly and helping whenever needed. Best part is how close it is to San Juan. The neighborhood it's in can be sketch for some people, but try to believe me, you are good. The condition of the room could've been better. Spots on the couch, unkept rug, floor tiles lifting, ceiling peeling. None of it was eggrecious to a point we didn't feel comfortable, but more so details missed that can be improved. You also don't have a view out to anytign but an empty lot with graffiti on an abandoned building. BUT if you're looking for somewhere to simply sleep and change clothes, this is perfect. Lol honestly it's a very ok, 3/5, 5-6/10 place. You'll only be disappointed thinking you're staying at a Marriott. BRING YOUR OWN WASH CLOTHS AND TOWELS. Lol they run out fast.

Reviewed on Mar 19, 2026

![Enjoy our Luxurious Penthouse in Condado](https://images.trvl-media.com/lodging/121000000/120050000/120044800/120044729/b71982f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Enjoy our Luxurious Penthouse in Condado

Santurce

CA $1,593

per person

Jun 1 - Jun 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

No reviews

![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 $1,316

per person

May 11 - May 15

found 10 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to San Juan (SJU)

9.2/10 Wonderful! (469 reviews)

We stayed a week and had a wonderful experience. The hotel is located near everything you need and the beach view was memorable. The shower! The shower! The shower! We have been trying to figure out how to make our shower at home, like the hotel shower.

Reviewed on Mar 20, 2026

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/2026-04-21/2026-04-28/?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/w1179h1813x0y16-f593ef9e_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 free WiFi, a beach locale, and patios. Popular attractions Ceiba Ferry Terminal and El Conquistador Golf Course ...

7.6/10 Good! (4 reviews)

Peaceful

Reviewed on Feb 12, 2026

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

[See all 2,124 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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## 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)[

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