Find Hotels with a Pool in Windward Side from CA $141

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Check prices for these dates

Tonight
Nov 7 - Nov 8
Tomorrow
Nov 8 - Nov 9
Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Our top choices for Windward Side hotels with a pool

A rectangular swimming pool with a white tiled deck, surrounded by white railings and lounge chairs.

1. Saba Arawak Hotel

Saba Arawak Hotel
3.0 star property
Windward Side
8.2 out of 10, Very good, (109 reviews)
The price is CA $189
CA $223 total
includes taxes & fees
Nov 8 - Nov 9
Saba Arawak Hotel
A pool surrounded by lush greenery and a view of the ocean.

2. El Momo Cottages

El Momo Cottages
3.0 star property
Windward Side
8.6 out of 10, Excellent, (63 reviews)
The price is CA $191
CA $203 total
includes taxes & fees
Nov 14 - Nov 15
El Momo Cottages
A pool area with lounge chairs, a pergola, and a view of a mountain.

3. Scenery Hotel Saba

Scenery Hotel Saba
3.5 star property
Windward Side
The price is CA $362
CA $431 total
includes taxes & fees
Nov 18 - Nov 19
Scenery Hotel Saba
A pool with lounge chairs and a stone patio, surrounded by lush greenery and overlooking a hilly landscape.

4. Home a way from home in the Unspoiled queen of the Caribbean.

Home a way from home in the Unspoiled queen of the Caribbean.
Saba
10.0 out of 10, Exceptional, (4 reviews)
The price is CA $565
CA $615 total
includes taxes & fees
Dec 1 - Dec 2
Home a way from home in the Unspoiled queen of the Caribbean.
A multi-story building with a pool, outdoor seating, and a covered area with a sign reading 'Café à vins.'

5. The Old Gin House

The Old Gin House
3.0 star property
Oranjestad
8.4 out of 10, Very good, (65 reviews)
The price is CA $223
CA $238 total
includes taxes & fees
Nov 25 - Nov 26
The Old Gin House
A swimming pool with lounge chairs, a wooden deck, and a building with a red roof.

6. Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
3.0 star property
Oranjestad
8.2 out of 10, Very good, (20 reviews)
The price is CA $141
CA $151 total
includes taxes & fees
Dec 2 - Dec 3
Talk of the Town Inn & Suites
A pool with lounge chairs and umbrellas, overlooking a clear blue sea.

7. Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
4.0 star property
Oranjestad
9.6 out of 10, Exceptional, (32 reviews)
The price is CA $231
CA $247 total
includes taxes & fees
Dec 4 - Dec 5
Quill Gardens Boutique 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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Choose what matters most at hotels with a pool in Windward Side

Breakfast included
4 stars

Top Windward Side Hotel Reviews

A pool surrounded by lush greenery and a view of the ocean.
El Momo Cottages

El Momo Cottages

El Momo Cottages
Windward Side

10/10 Excellent

Was exactly as described, remote location with lots of stairs - well worth the walk, scenery was beautiful.
Canada
Georgina
Reviewed July 20, 2025
El Momo Cottages

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. Scenery Hotel Saba: Provides free self parking, an outdoor pool, and complimentary wireless internet access. Flamboyant Cottage - Spectacular View & Pool: Features complimentary wireless internet access, a pool, and kitchens. Spyglass is a Private Villa With 360 View Near Windwardside.: Offers kitchens, a pool, and televisions.

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, Harry L Johnson Museum, and Saba Heritage Center.

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.