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.

![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 $1,221

per person

Feb 15 - Feb 22

found 23 hours ago

Roundtrip flight included

Montreal Metropolitan Airport (YHU) 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 $1,301

per person

Jan 25 - Feb 1

found 16 hours ago

Roundtrip flight included

Hamilton (YHM) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Just overall a great place… close to everything. Very friendly staff..

Reviewed on Dec 13, 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 $1,751

per person

Feb 15 - Feb 22

found 23 hours ago

Roundtrip flight included

Montreal Metropolitan Airport (YHU) to San Juan (SJU)

9/10 Wonderful! (500 reviews)

Staff were very helpful keeping us from getting a parking ticket. The room we stayed in was very clean and met our need for one night but unfortunately we would not return. This building is a renovated storage building in the Old San Juan port area. The area does not feel safe for walking after dark. Additionally, if you’re a light sleeper you may find the noise keeping you up into the wee hours.

Reviewed on Dec 13, 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 $2,230

per person

Feb 15 - Feb 22

found 23 hours ago

Roundtrip flight included

Montreal Metropolitan Airport (YHU) 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 $2,275

per person

Feb 4 - Feb 11

found 11 hours 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

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/2026-01-14/2026-01-21/?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 $2,703

per person

Feb 15 - Feb 22

found 23 hours ago

Roundtrip flight included

Montreal Metropolitan Airport (YHU) to San Juan (SJU)

9.2/10 Wonderful! (1,616 reviews)

Beach view was excellent.

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 $3,608

per person

Feb 4 - Feb 10

found 14 hours ago

Roundtrip non-stop flight included

Calgary (YYC) 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 $8,946

per person

Feb 13 - Feb 20

found 1 day 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/2026-01-14/2026-01-21/?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 $849

per person

Jan 28 - Jan 31

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Just overall a great place… close to everything. Very friendly staff..

Reviewed on Dec 13, 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 $867

per person

Jan 28 - Jan 31

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9/10 Wonderful! (500 reviews)

Staff were very helpful keeping us from getting a parking ticket. The room we stayed in was very clean and met our need for one night but unfortunately we would not return. This building is a renovated storage building in the Old San Juan port area. The area does not feel safe for walking after dark. Additionally, if you’re a light sleeper you may find the noise keeping you up into the wee hours.

Reviewed on Dec 13, 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 $1,602

per person

Jan 23 - Jan 26

found 15 hours 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

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/2026-01-14/2026-01-21/?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.

![Lazy Parrot Inn](https://images.trvl-media.com/lodging/1000000/910000/900400/900306/77384e02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Lazy Parrot Inn

CA $631

per person

Mar 7 - Mar 11

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (1,000 reviews)

Nice rooms, relaxing environment and great staff. The Lazy Parrot Inn location allows easy and quick access to everything needed for a great stay/vacation.

Reviewed on Dec 13, 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

found 24 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to San Juan (SJU)

9.2/10 Wonderful! (589 reviews)

Just overall a great place… close to everything. Very friendly staff..

Reviewed on Dec 13, 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 $967

per person

Feb 16 - Feb 20

found 24 hours 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

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/2026-01-14/2026-01-21/?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

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