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.

![DUNA by DW](https://images.trvl-media.com/lodging/79000000/78740000/78739700/78739626/83641b59_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### DUNA by DW

Santurce

CA $2,030

per person

Mar 24 - Mar 31

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to San Juan (SJU)

9.6/10 Exceptional! (58 reviews)

Beautiful room, super clean, very accommodating.

Reviewed on Jan 28, 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 $2,345

per person

Apr 16 - Apr 22

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Room was clean and spacious. Hotel employees were friendly and helpful. Parking is really tight and limited.

Reviewed on Jan 29, 2026

![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 $3,921

per person

Mar 21 - Mar 26

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to San Juan (SJU)

9.2/10 Wonderful! (126 reviews)

The room was gorgeous and staff went above and beyond their regular duties, at our beck and call. I will definitely return.

Reviewed on Jan 24, 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 $2,107

per person

Apr 16 - Apr 22

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to San Juan (SJU)

9/10 Wonderful! (328 reviews)

Great location, nice accommodations.

Reviewed on Jan 28, 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 $3,218

per person

Mar 22 - Mar 29

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to San Juan (SJU)

9/10 Wonderful! (645 reviews)

Room was nice but small with a curious layout. Whole facility was nice and staff were very courteous and efficient. Sister property next door has a nice restaurant

Reviewed on Jan 24, 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/2026-02-28/2026-03-07/?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.

![Hugo's Rental](https://images.trvl-media.com/lodging/109000000/108770000/108768900/108768837/75f55ce2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hugo's Rental

Old San Juan

CA $1,460

per person

Mar 21 - Mar 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.4/10 Exceptional! (241 reviews)

Great service, Marilu was incredibly attentive with our needs. Beautiful and clean place. Great location. Thank you

Reviewed on Jan 28, 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 $2,917

per person

Apr 9 - Apr 16

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

7.6/10 Good! (128 reviews)

One of the best hotels in PR

Reviewed on Jan 2, 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 $2,977

per person

Apr 18 - Apr 25

found 19 hours ago

Roundtrip flight included

Hamilton (YHM) to San Juan (SJU)

9.2/10 Wonderful! (1,616 reviews)

The overall experience was amazing. The amenities were so perfect and it was the best choice for my friends and I when staying in PR. Only complaint is the cleaning crew wasn’t as on top of it.

Reviewed on Jan 28, 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/2026-02-28/2026-03-07/?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 $1,054

per person

Apr 17 - Apr 20

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Room was clean and spacious. Hotel employees were friendly and helpful. Parking is really tight and limited.

Reviewed on Jan 29, 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 $1,378

per person

Apr 17 - Apr 20

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

9/10 Wonderful! (645 reviews)

Room was nice but small with a curious layout. Whole facility was nice and staff were very courteous and efficient. Sister property next door has a nice restaurant

Reviewed on Jan 24, 2026

![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 $1,057

per person

Mar 10 - Mar 13

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

8.6/10 Excellent! (577 reviews)

The staff was great, the area was great and property was great

Reviewed on Jan 28, 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/2026-02-28/2026-03-07/?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.

![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 $1,144

per person

Apr 13 - Apr 17

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (328 reviews)

Great location, nice accommodations.

Reviewed on Jan 28, 2026

![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 $1,341

per person

Apr 13 - Apr 17

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

8.6/10 Excellent! (577 reviews)

The staff was great, the area was great and property was great

Reviewed on Jan 28, 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/2026-02-28/2026-03-07/?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)

This property was truly a beach house. It was exactly what we wanted. Close enough to areas with great restaurants and beaches to visit, but secluded enough to feel like you were on a private island. The hosts were always quick to respond to questions or concerns. We will definitely stay here again ...

Reviewed on Jan 21, 2026

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

[See all 2,203 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)[

Roosevelt Roads Vacations

](https://expedia.ca/Roosevelt-Roads.d6360451.Destination-Travel-Guides)

\* 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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