Photo by Meghan Watters

Hotels with Pool & Resorts in Windward Side from NZ$180

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Best Windward Side Hotels with Pool

El Momo Cottages
3.0 star property
8.6 out of 10, Excellent, (47)
"I had a wonderful visit at El Momo. I was in Saba for hiking and the cottages were nestled into the woods, giving the perfect setting for enjoying the natural surroundings. The view from the cottages was amazing, the pool was a perfect spot to relax after a day out. The staff was helpful and friendly. "
The price is NZ$180
includes taxes & fees
24 Nov - 25 Nov
El Momo Cottages
Juliana's Hotel
Juliana's Hotel
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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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's it like visiting Windward Side?
If lounging by a pool is your idea of the perfect getaway, you might want to think about scenic Windward Side, which has 6 places to stay with pools. During your visit, you can explore sights such as Dutch Museum of Saba and Mt Scenery, and then unwind poolside at one of the accommodation options in Windward Side that guests like for their pools.
What are some accommodation options with pools in Windward Side?
Saba Arawak Hotel: Features complimentary high-speed (wired) Internet access, an outdoor pool and free self parking. El Momo Cottages: Offers complimentary wireless Internet access, an outdoor pool and a restaurant. Flamboyant Cottage - Spectacular View & Pool: Provides kitchens, a pool and televisions. Spyglass is a Private Villa With 360 View Near Windwardside.: Features complimentary wireless Internet access, an outdoor pool and kitchens. Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!: Provides complimentary wireless Internet access, an outdoor pool and kitchens.
How many hotels with pools will I be able to find in Windward Side?
Expedia has 6 hotels in Windward Side for your poolside break.
What is there to see and do in Windward Side?
Take in the natural beauty with a stop at Mt Scenery. During your stay, visit sights such as Dutch Museum of Saba, Saba Heritage Center and Harry L Johnson Museum.
When is the best time to book a hotel with a pool in Windward Side?
Taking the local weather in Windward Side 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 October, with an average temperature of 28°C, while the coldest months are February and March, with an average of 26°C. Average annual precipitation for Windward Side is 921 mm.