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Top Pet-friendly Caribbean Islands Hotels

Sunshine Suites Resort

1465 Esterley Tibbetts Seven Mile Beach Grand Cayman

44 hours drive from Windward Islands

Stay at this beach hotel in Seven Mile Beach. Enjoy breakfast (surcharge), room service and beach cabanas (surcharge). Our guests praise the restaurant and the ...

8.8/10 Excellent! (1,000 reviews)

Newly renovated. Clean rooms. Pool and restaurant wasn’t open but we had full access to the Westin facilities where we spent the day, which was great!

Reviewed on 8 Dec 2025

Rincon of the Seas - Grand Caribbean Hotel

Road 115 Km 12.2 Rincon

18 hours drive from Windward Islands

Stay at this beach hotel in Rincon. Enjoy free parking, a beach locale and a rooftop terrace. Our guests praise the pool and the helpful staff in their reviews. ...

9/10 Wonderful! (1,082 reviews)

Beautiful views and clean rooms!

Reviewed on 12 Dec 2025

Condado Vanderbilt Hotel

1055 Ashford Avenue San Juan

17 hours drive from Windward Islands

Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, 4 outdoor pools and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...

9.2/10 Wonderful! (1,654 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 ...

Reviewed on 9 Dec 2025

See all 84,879 properties in Caribbean Islands

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.