Hotels with Pool & Resorts in Middlesex

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Best Middlesex Hotels with Pool

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

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

Frequently asked questions

What are some hotels with pools in Middlesex?
SeaGarden Beach Resort - All Inclusive: Property, 8-minute walk from Doctor’s Cave Beach. Features a children’s pool, an outdoor pool and 3 restaurants. S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel: Property steps from Doctor’s Cave Beach. Offers 2 restaurants, 2 outdoor swimming pools and a full-service spa. Grand Palladium Lady Hamilton Resort & Spa All Inclusive: Provides 5 outdoor swimming pools, a children’s pool and a private beach. Grand Palladium Jamaica Resort & Spa All Inclusive: Features 5 outdoor swimming pools, a children’s pool and a private beach. Hotel Riu Palace Tropical Bay - All Inclusive: Property, 4-minute walk from Jamaica Beaches. Offers 2 outdoor swimming pools, a children’s pool and 5 restaurants.
What is there to see and do in Middlesex?
Explore places such as Seven Mile Beach while you’re in the area. Make a point to visit attractions such as Bloody Bay and Kool Runnings Water Park.
When is the best time to book a hotel with a pool in Middlesex?
Taking the local weather in Middlesex into account can help you maximise your time at the pool during your trip. The hottest months are usually August and September, with an average temperature of 28°C, while the coldest months are February and January, with an average of 26°C. The rainiest months in Middlesex are May, October, September and August, with each month seeing an average of 214 mm of rainfall.