Hotels with Pool & Resorts in Cudjoe Head

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Best Cudjoe Head Hotels with Pool

Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

What are some accommodation options with pools in Cudjoe Head?
Secluded Villa with scenic views of the Atlantic ocean: Features sunloungers, an outdoor pool and kitchens.
What is there to see and do in Cudjoe Head?
Take a walk along the waterfront at Woodlands Beach and Lime Kiln Beach. During your stay, visit sights such as Montserrat Volcano Observatory, Montserrat National Trust and Soufriere Hills Volcano.
When is the best time to book a hotel with a pool in Cudjoe Head?
Taking the local weather in Cudjoe Head into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually September and August, with an average temperature of 28°C, while the coldest months are February and January, with an average of 26°C. Average annual precipitation for Cudjoe Head is 886 mm.