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Windward Side Holiday Rentals

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Check prices for these dates

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Holiday Rentals in Windward Side

Outdoor dining
Spyglass is a Private Villa With 360 View Near Windwardside.
Spyglass is a Private Villa With 360 View Near Windwardside.
9.8 out of 10, Exceptional, (69)
"This property is absolutely stunning! Views are amazing and just a really great place to stay. "
United States
Wendy N.
Spyglass is a Private Villa With 360 View Near Windwardside.
Property grounds
Flamboyant Cottage - Spectacular View & Pool
Flamboyant Cottage - Spectacular View & Pool
9.8 out of 10, Exceptional, (40)
"Great experience. Trisha and Michael were more than welcoming and helpful. Incredible location and views. "
United States
J Geoffrey O.
Flamboyant Cottage - Spectacular View & Pool
Property grounds
Peter Hytte is close to everything at great price!
Peter Hytte is close to everything at great price!
10.0 out of 10, Exceptional, (3)
"It's safe to say I could absolutely live here!!! This cottage is in the heart! Jeffery is amazing. He's helpful, laid back and kind LIKE EVERYONE here! I'm booking again soon. Where else can you sleep with all your doors and windows open in nature and be safe?"
United States
Gina
Peter Hytte is close to everything at great price!
Property grounds
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
10.0 out of 10, Exceptional, (11)
"Very pleased with the responsiveness of the owner, and location of the property. Exactly what we were looking for. Hope to stay again."
United States
Alan F.
Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
Terrace/patio
Home a way from home in the Unspoiled queen of the Caribbean.
Home a way from home in the Unspoiled queen of the Caribbean.
10.0 out of 10, Exceptional, (3)
"Iris House is cute, comfortable, great/walkable location and with everything we needed for a great stay. Owner and manager both very helpful - highly recommend."
United States
Margaret K.
Home a way from home in the Unspoiled queen of the Caribbean.
Front of property
Palm Spring Inn
Palm Spring Inn
3.0 star property
8.6 out of 10, Excellent, (14)
"Great place lovely staff"
United States
Dameon
The price is HK$894
HK$992 total
includes taxes & fees
24 Oct - 25 Oct
Palm Spring Inn
Outdoor pool
Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
10.0 out of 10, Exceptional, (4)
"Literally on the edge of runway to view planes taking off and excellent view of mountains/ocean."
United States
James
Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
Fridge, microwave, oven, stovetop
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
The price is HK$1,049
HK$1,246 total
includes taxes & fees
30 Oct - 31 Oct
Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad
Fridge, microwave, oven, stovetop
Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
The price is HK$1,049
HK$1,246 total
includes taxes & fees
30 Oct - 31 Oct
Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad
Terrace/patio
Cozy 2-bedroom apartment with AC, WiFi in fabulous Oranjestad
Cozy 2-bedroom apartment with AC, WiFi in fabulous Oranjestad
Cozy 2-bedroom apartment with AC, WiFi in fabulous Oranjestad
Exterior
Studio apartment in quiet neighborhood.
Studio apartment in quiet neighborhood.
Studio apartment in quiet neighborhood.
Pool
Welcome To Casa Sabean, a Paradise in Paramira! 4 Bedroom with Pool
Welcome To Casa Sabean, a Paradise in Paramira! 4 Bedroom with Pool
2.0 star property
Welcome To Casa Sabean, a Paradise in Paramira! 4 Bedroom with Pool
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

Saba Arawak Hotel

Saba Arawak Hotel

10/10 Excellent
"It was an amazing experience "
Shandelle 1-night trip
Posted 1 month ago
Saba Arawak Hotel

Find out more about Windward Side

Search for holiday rentals in Windward Side on Expedia! You can easily find your home rentals, villas, holiday apartments in Windward Side using one of the methods below:

  • View our selection of featured holiday rentals in Windward Side
  • Use the map to find apartments and other holiday homes in the Windward Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windward Side while they last

Look no further and take a look at our great range of rental properties in Windward Side!

Frequently asked questions

Are there holiday rentals in Windward Side?

Yes, there are holiday rentals close to the most popular sights in Windward Side, or you can select 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 holiday rentals that Windward Side has to offer?

Home a way from home in the Unspoiled queen of the Caribbean.: This highly rated holiday home rental in Windward Side is located in the city centre, and has an outdoor pool, a patio and a BBQ 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 holiday with amenities such as a garden.

How many holiday rentals are there in Windward Side?

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

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

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

What’s a holiday rental in Windward Side like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windward Side. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a small group gathering.