Windward Side Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Windward Side vacation rentals

A pool with lounge chairs and a stone patio, surrounded by lush greenery and overlooking a hilly landscape.

1. 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 house was amazing we will be back again… Thank you Michael!"
United States
Tim L.
The price is CA $571
CA $621 total
includes taxes & fees
Dec 15 - Dec 16
Home a way from home in the Unspoiled queen of the Caribbean.
A paved pathway flanked by palm trees and buildings with a clear sky above.

2. Palm Spring Inn

Palm Spring Inn
3.0 star property
Oranjestad
8.2 out of 10, Very good, (16 reviews)
"It not a place that have amenities to enjoy. For rest and go it is ok."
United States
Ivan W
The price is CA $205
CA $228 total
includes taxes & fees
Nov 18 - Nov 19
Palm Spring Inn
An outdoor patio with a table and chairs, a wicker sofa, and a view of the ocean.

3. Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views

Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
Sint Eustatius
8.0 out of 10, Very good, (1 review)
The price is CA $228
CA $304 total
includes taxes & fees
Nov 21 - Nov 22
Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views
A courtyard with a central paved area, surrounded by a white building with multiple floors and balconies.

4. Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad

Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
Oranjestad
7.0 out of 10, Good, (2 reviews)
"The appartment is spacious and has everything you need. It was very neat and clean and the host Davon fast in response. The location is a quiet neighbourhood, not far away from the center. Thanks for having us. "
Netherlands
sytske m.
The price is CA $228
CA $254 total
includes taxes & fees
Nov 20 - Nov 21
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
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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Top Windward Side Hotel Reviews

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

Saba Arawak Hotel

Saba Arawak Hotel
Windward Side

10/10 Excellent

Travelling to Saba was on our "bucket list". We knew where it was but not much else. This is a small island and not a resort experience. If you like to hike then this is the place. Same with diving. Leave your expectations at home. We stayed at the Arawak Hotel for 4 nights in late October. We had a one bedroom with a partial kitchen. The location was great, the view fantastic, and the Hotel quaint. The Arawak is being upgraded constantly but supplies are hard to get on Saba, so be...
Canada
Duane
Reviewed December 11, 2023
Saba Arawak Hotel

Find out more about Windward Side

Everything you need to know about Windward Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windward Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windward Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windward Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windward Side. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windward Side vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windward Side vacation rentals we have selected for you start as low as CA $205 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windward Side rentals

At Expedia, we put the best Windward Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windward Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windward Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windward Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Windward Side?

Yes, we give you a choice of vacation rentals near top local attractions in Windward Side, or you can go with a more secluded option if you're looking for a relaxing stay. Windward Side is known for its seaside and mountain views.

What are some of the best vacation rentals that Windward Side has to offer?

Home a way from home in the Unspoiled queen of the Caribbean.: This Windward Side vacation home rental is located in the city center and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a garden. Another good choice for your trip to Windward Side is Beautiful Traditional Saba Cottage With all the Modern Amenities.

How many vacation rentals are there in Windward Side?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Windward Side stay.

What’s there to see and do in Windward Side?

Cultural attractions include Dutch Museum of Saba and Harry L Johnson Museum, whereas Mt Scenery is one spot to enjoy nature. Other places in town to visit include Saba Heritage Center and Jo Bean Glass Art Studio.

What’s a vacation rental in Windward Side like?

A vacation rental is a private property where you can stay for several days or longer in Windward Side. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.