View of Saba and Statia (Sint Eustatius) in the Dutch Caribbean from the north coast of Saint Kitts

Hotels with Pool & Resorts in Windward Side from AU$163

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Check availability on Windward Side Hotels with Pool

Our top choices for Windward Side hotels with a pool

Exterior

Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (27 reviews)
The price is AU$231
includes taxes & fees
10 July - 11 July
Quill Gardens Boutique Hotel
Outdoor pool, pool loungers

The Old Gin House

The Old Gin House
3.0 star property
Oranjestad
8.4 out of 10, Very good, (62 reviews)
The price is AU$288
includes taxes & fees
20 June - 21 June
The Old Gin House
Outdoor pool

Saba Arawak Hotel

Saba Arawak Hotel
3.0 star property
Windward Side
8.4 out of 10, Very good, (92 reviews)
The price is AU$225
includes taxes & fees
21 June - 22 June
Saba Arawak Hotel
Outdoor pool, pool loungers

Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
3.0 star property
Oranjestad
8.6 out of 10, Excellent, (18 reviews)
The price is AU$163
includes taxes & fees
3 July - 4 July
Talk of the Town Inn & Suites
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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Choose what matters most at hotels with a pool in Windward Side

Breakfast included
4 stars

Top Windward Side Hotel Reviews

The Old Gin House

The Old Gin House

10/10 Excellent
"Excellent "
Christine 3-night trip
Posted 1 month ago
The Old Gin House
El Momo Cottages

El Momo Cottages

10/10 Excellent
"Loved this place as so simply beautiful and relaxed. Not suitable if struggle with mobility as located up a steep hill / steps ... But worth the view. "
lucy 2-night trip
Posted 4 months ago
El Momo Cottages

Frequently asked questions

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 laundry facilities. 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, a pool and kitchens. Peter Hytte is close to everything at great price!: Offers free self parking, an outdoor pool and complimentary wireless Internet access.
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 Saba Heritage Center, Dutch Museum of Saba 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.