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

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Check availability on Windward Side Hotels with a Pool

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul

Our top choices for Windward Side hotels with a pool

Outdoor pool, sun 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 AED 458
AED 491 total
includes taxes & fees
22 Jun - 23 Jun
Talk of the Town Inn & Suites
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 AED 496
AED 583 total
includes taxes & fees
22 Jun - 23 Jun
Saba Arawak Hotel
Exterior

Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (28 reviews)
The price is AED 622
AED 671 total
includes taxes & fees
25 Jun - 26 Jun
Quill Gardens Boutique Hotel
Outdoor pool, sun 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 AED 697
AED 746 total
includes taxes & fees
25 Jun - 26 Jun
The Old Gin House
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

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Frequently asked questions

What are some accommodations with pools in Windward Side?
Saba Arawak Hotel: Features complimentary 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 complimentary wireless internet access, a pool, and kitchens. Spyglass is a Private Villa With 360 View Near Windwardside.: Offers kitchens, a pool, and televisions. 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, check out 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 into account the local weather in Windward Side is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually September and October with an average temp of 83°F, while the coldest months are February and March with an average of 78°F. Average annual precipitation for Windward Side is 36 inches.