A calm sea with a mountain in the distance.

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Check availability on Windward Side Hotels with a Pool

Tonight
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

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.
A coastal landscape with clear turquoise waters, rocky shoreline, and green hills.
A hotel with multiple balconies, outdoor seating, and a view of the sea.
A buffet table with various food items and a selection of wine bottles.

1. Saba Arawak Hotel

Saba Arawak Hotel
Windward Side
￥19,926
￥23,434 total
includes taxes & fees
Sep 18 - Sep 19
Saba Arawak Hotel
A pool area with lounge chairs, a pergola, and a view of a mountain.
A rooftop terrace with two lounge chairs under a large umbrella, surrounded by potted plants and a wooden fence.
A modern interior with a high ceiling, a sofa, ottomans, and potted plants.
A modern bathroom with a glass-enclosed shower, a toilet, and a sink with a stone basin.

2. Scenery Hotel Saba

Scenery Hotel Saba
Windward Side
￥47,894
￥55,151 total
includes taxes & fees
Sep 18 - Sep 19
Scenery Hotel Saba
A swimming pool with a stone border, surrounded by blue lounge chairs and a stone wall.
A covered outdoor seating area with blue chairs and a pool, overlooking a mountainous landscape.
A kitchen with a gas stove, microwave, toaster, and wooden cabinets.
A bedroom with a bed, a ceiling fan, an air conditioning unit, a window, and a door leading to another room.

3. 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
￥62,052
￥70,584 total
includes taxes & fees
Sep 30 - Oct 1
Home a way from home in the Unspoiled queen of the Caribbean.
A swimming pool with lounge chairs, a wooden deck, and a building with a red roof.
A bedroom with a large bed, a window with a view, a painting on the wall, and a wooden door.
A cozy room with a high ceiling, large windows, a sofa, two wicker chairs, and a wooden table.
A covered patio area with a table and chairs, a door labeled 207, and a window with curtains.

4. Talk of the Town Inn & Suites

Talk of the Town Inn & Suites
Oranjestad
￥15,378
￥16,454 total
includes taxes & fees
Oct 10 - Oct 11
Talk of the Town Inn & Suites
A multi-story building with a pool, balconies, and outdoor seating.
A beach with palm trees, a stone wall, and a building in the background.
A brick building with a balcony, green shutters, and a garden with various plants.
A room with a brick wall, wooden floor, a brown leather sofa, and two large arched windows with a view of greenery.

5. The Old Gin House

The Old Gin House
Oranjestad
￥26,225
￥28,157 total
includes taxes & fees
Sep 18 - Sep 19
The Old Gin House
A clear blue pool with a wooden deck, white railings, and a view of the ocean and mountains in the background.
A pathway lined with palm trees and tropical plants, leading to a building with a blue facade.
A hallway with tiled flooring, large vases with flowers, and a painting on the wall.
A breakfast table set with plates, cutlery, a vase of flowers, and a view of the ocean.

6. Quill Gardens Boutique Hotel

Quill Gardens Boutique Hotel
Oranjestad
￥25,578
￥27,368 total
includes taxes & fees
Sep 18 - Sep 19
Quill Gardens Boutique Hotel
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Choose what matters most at hotels with a pool in Windward Side

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Windward Side Hotel Reviews

El Momo Cottages

El Momo Cottages

10/10 Excellent
"El Momo Cottage is a simple basic place you will love, if you just want to take a break and go back to basic. The wooden cabin located in hill with an awesome view. I return home fully rested and recharged. Just by staying there. Definitely I'm going back. It's my retraer in the unspoiled queen called Saba"
Wendell 5-night trip
Posted 1 month ago
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. The Cottage Club Hotel: Provides free self parking, an outdoor pool, and complimentary wireless internet access. Scenery Hotel Saba: Features free self parking, an outdoor pool, and complimentary wireless internet access. Flamboyant Cottage - Spectacular View & Pool: Offers 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 Dutch Museum of Saba, Harry L Johnson Museum, and Jo Bean Glass Art Studio.
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.