The Best Hotels with a Pool in Windward Side from SAR 422 in 2026

Q: 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 a restaurant. The Cottage Club Hotel : Provides free self parking, an outdoor pool, and complimentary wireless internet access. Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away! : Features kitchens, a pool, and televisions. Flamboyant Cottage - Spectacular View & Pool : Features complimentary wireless internet access, a pool, and kitchens.

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Our top choices for Windward Side hotels with a pool

Saba Arawak Hotel

Windward Side

SAR 596 total

includes taxes & fees

14 Apr - 15 Apr

El Momo Cottages

Windward Side

SAR 422 total

includes taxes & fees

19 Apr - 20 Apr

Quill Gardens Boutique Hotel

Oranjestad

SAR 618 total

includes taxes & fees

13 Apr - 14 Apr

Talk of the Town Inn & Suites

Oranjestad

SAR 433 total

includes taxes & fees

7 May - 8 May

The Old Gin House

Oranjestad

SAR 736 total

includes taxes & fees

18 Apr - 19 Apr

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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

8/10 Good

"There is no shuttle. Someone at the airport got us a taxi. The hotel did not help in any way in us getting to the hotel. Important to know.....you are on your own to and from the hotel. Heads up hotel.com would not let me post this"

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. "

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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 a restaurant. The Cottage Club Hotel: Provides free self parking, an outdoor pool, and complimentary wireless internet access. Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!: Features kitchens, a pool, and televisions. Flamboyant Cottage - Spectacular View & Pool: Features complimentary wireless internet access, a pool, and kitchens.

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 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 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.

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