Photo by Staci Partlo

Hotels with Pool & Resorts in Leeward Settlement

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Best Leeward Settlement 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.

Frequently asked questions

What's it like visiting Leeward Settlement?
If taking it easy by the pool is your idea of a great holiday, you might want to think about Leeward Settlement, which has 60 places to stay with pools. While you’re visiting, you can explore sights such as Grace Bay Beach and Turtle Cove, and then unwind poolside at one of the accommodation options in Leeward Settlement that guests like for their pools.
What are some accommodation options with pools in Leeward Settlement?
Blue Haven Resort - All Inclusive: Property located near Grace Bay Beach. Features a private beach, an outdoor pool and 3 restaurants. The Atrium Resort: Aparthotel located near Grace Bay Beach. Offers a children’s pool, an outdoor pool and a full-service spa. Villa KendaraBK APRIL 5th ONPrivateGatedSeaFront GuestHouse~Panoramic View: Guest house located near Grace Bay Beach. Provides sunloungers, a pool and complimentary wireless Internet access. Checkers Vacation Homes: Aparthotel, 14-minute walk from Grace Bay Beach. Offers free self parking, an outdoor pool and complimentary wireless Internet access. Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2: Villa located near Grace Bay Beach. Features kitchens, a pool and televisions.
How many pool hotels will I find in Leeward Settlement?
Expedia’s 60 hotels in Leeward Settlement give you a great choice for your poolside getaway.
What is there to see and do in Leeward Settlement?
Explore places such as Grace Bay Beach while you’re in Leeward Settlement. Spend some time experiencing the great outdoors at Leeward Beach and Long Bay Beach.
When is the best time to book a hotel with a pool in Leeward Settlement?
Taking the local weather in Leeward Settlement 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 March and February, with an average of 25°C. Average annual precipitation for Leeward Settlement is 783 mm.