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.
Ola Boutique Hotel

Ola Boutique Hotel

Condado
CA $918
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (925 reviews)
My stay at the Ola Boutique was absolutely amazing. The staff was very accommodating to our every need and request. The hotel was clean and the breakfast was great. Customer service provided by Elliott and the staff was phenomenal. I truly enjoyed Elliott's courtesy, recommendations, kindness, professionalism and hospitality. Elliott gave us insight on Puerto Rico's rich history and culture. I wish I could have spent more time in Puerto Rico just due to the service at the beautiful hotel. The vibe from the bar and outside lounge was definitely on point. Our rooms were cleaned promptly and we appreciated having access to cold water, tasty coffee and a variety of sodas and adult drinks. My hope is to return to Puerto Rico. And when I do, my first choice of lodging will be the Ola Boutique. If Elliott and the current staff are still employed there, that will definitely be an additional bonus to our stay.

Reviewed on Aug 18, 2026

Hotel Puerto Valdes

Hotel Puerto Valdes

Puerta de Tierra
CA $1,111
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
8.8/10 Excellent! (713 reviews)
OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

Condado
CA $1,411
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
8.8/10 Excellent! (727 reviews)
The room was exactly as pictured. All the staff were friendly and our housekeeper did an exceptional job cleaning the room each day. The property is in a walkable area and walking distance to the beach.

Reviewed on Aug 18, 2026

Aire de O:live

Aire de O:live

Isla Verde
CA $1,380
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
9.2/10 Wonderful! (736 reviews)
One of the BEST hotels in San Juan!

Reviewed on Aug 17, 2026

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5* Pet-friendly holidays in Roosevelt Roads

Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

Isla Verde
CA $1,278
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
8.6/10 Excellent! (2,152 reviews)
Fairmont El San Juan Villa Experience

Fairmont El San Juan Villa Experience

Isla Verde
CA $1,720
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
7.6/10 Good! (150 reviews)
Exceeded our expectations in cleanliness, staff was courteous went out of their way to make sure our stay was memorable.

Reviewed on Aug 14, 2026

Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

Condado
CA $1,443
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
9.4/10 Exceptional! (1,795 reviews)
Great staff

Reviewed on Aug 18, 2026

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3 Night Pet-friendly holidays in Roosevelt Roads

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

Hotel Puerto Valdes

Puerta de Tierra
CA $878
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to San Juan (SJU)
8.8/10 Excellent! (713 reviews)
Beach Front  Amapola SeaSide Apt

Beach Front Amapola SeaSide Apt

Isla Verde
CA $1,585
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
10/10 Exceptional! (7 reviews)
Beautiful ocean view. Easy access to beach.

Reviewed on Jul 26, 2026

Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

Isla Verde
CA $1,039
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to San Juan (SJU)
8.6/10 Excellent! (2,152 reviews)
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4 Night Pet-friendly holidays in Roosevelt Roads

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

Hotel Puerto Valdes

Puerta de Tierra
CA $926
per person
Nov 9 - Nov 13
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.8/10 Excellent! (713 reviews)
Isla Verde Beachfront Retreat With Parking

Isla Verde Beachfront Retreat With Parking

Isla Verde
CA $1,022
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
10/10 Exceptional! (2 reviews)
Casa Ciana

Casa Ciana

Santurce
CA $1,342
per person
Nov 5 - Nov 9
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9.6/10 Exceptional! (513 reviews)
The rooms were nice and it was clean.

Reviewed on Aug 8, 2026

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Pet-friendly Hotels in Roosevelt Roads

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

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 El Conquistador Golf Course and Ceiba Ferry Terminal ...
8/10 Very good! (6 reviews)
"The house was beautiful but it was way overpriced for how difficult it was to find it and get to it. It also smells terrible there because of the sarragassum. We were notified a couple days in advance of how bad it smelled but you could tell that there was weeks of horribly smelly sarragassum rotting ..."

Reviewed on Aug 1, 2026

Mami Ana Beach House.10min ferry Vieques/Culebra. Beautifull, excelent location
See all 2,256 properties in Roosevelt Roads
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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