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

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

Photo by Shannon Willitts 

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## 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 $894

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 $2,048

per person

Feb 13 - Feb 20

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

He staff was extremely friendly! Great neighborhood. Rooms and bathroom clean! Quiet area. The rooms we had were nice and big to fit us all! It was great they made everything so convenient!

Reviewed on Dec 9, 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 $2,639

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to San Juan (SJU)

9/10 Wonderful! (328 reviews)

Yes the beach was across from the hotel.

Reviewed on Dec 8, 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 $2,819

per person

Jan 19 - Jan 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (126 reviews)

Everything was great

Reviewed on Dec 4, 2025

![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 $2,764

per person

Mar 1 - Mar 8

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (645 reviews)

Tatiana was a great host who helped us out tremendously.

Reviewed on Nov 30, 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/2026-01-09/2026-01-16/?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 $3,083

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to San Juan (SJU)

9.2/10 Wonderful! (1,616 reviews)

What they do well, they do really well. Staff was incredible across the board. Commodore suite was beautiful. The overall grounds are very well maintained. Only complaint i have is that the butler service was advertised as 24/7 but were only there part of the day, were hard to get ahold of, and changed daily. Other guests that we attended a tour with seemed to get much better service so perhaps we just got a dud, but it was disappointing. Overall a terrific stay though.

Reviewed on Dec 9, 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 $3,467

per person

Feb 10 - Feb 15

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) 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 $3,829

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to San Juan (SJU)

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

Beautiful resort. Sad we only had one night to stay as we were traveling through to another island.

Reviewed on Dec 8, 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/2026-01-09/2026-01-16/?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 $1,244

per person

Mar 6 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

He staff was extremely friendly! Great neighborhood. Rooms and bathroom clean! Quiet area. The rooms we had were nice and big to fit us all! It was great they made everything so convenient!

Reviewed on Dec 9, 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 $1,982

per person

Jan 16 - Jan 19

found 2 hours ago

Roundtrip non-stop flight included

Montreal (YUL) 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

![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 $1,793

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to San Juan (SJU)

9/10 Wonderful! (645 reviews)

Tatiana was a great host who helped us out tremendously.

Reviewed on Nov 30, 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/2026-01-09/2026-01-16/?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.

![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 $821

per person

Feb 22 - Feb 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

He staff was extremely friendly! Great neighborhood. Rooms and bathroom clean! Quiet area. The rooms we had were nice and big to fit us all! It was great they made everything so convenient!

Reviewed on Dec 9, 2025

![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 $959

per person

Feb 22 - Feb 26

found 1 day ago

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

![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 $1,346

per person

Feb 22 - Feb 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (328 reviews)

Yes the beach was across from the hotel.

Reviewed on Dec 8, 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/2026-01-09/2026-01-16/?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 2,118 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.

## More vacations you might like

![](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)

## 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.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app