Title: Windward Side Vacation Home Rentals from CA $159: Search Top Private Vacation Homes for Rent | Expedia.ca

[Hotels in Windward Side](https://expedia.ca/Windward-Side-Hotels.d11638.Travel-Guide-Hotels)[Vacation Rentals in Windward Side](https://expedia.ca/Windward-Side-Vacation-Rentals.d11638.Travel-Guide-VacationRentals)[Things to do in Windward Side](https://expedia.ca/Things-To-Do-In-Windward-Side.d11638.Travel-Guide-Activities)[Windward Side Car Rentals](https://expedia.ca/Car-Rentals-In-Windward-Side.d11638.Car-Rental-Guide)[Windward Side Vacation Packages](https://expedia.ca/Windward-Side.d11638.Destination-Travel-Guides)

![The beautiful island of Saba](https://images.trvl-media.com/place/11638/bec9a351-370d-430b-b191-7beddd830e10.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Stills 'n' stories

![](https://images.trvl-media.com/place/11638/bec9a351-370d-430b-b191-7beddd830e10.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=11638&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Windward Side

![Outdoor pool](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d45b92b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/121cb9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d8a26561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; Caribbean cuisine, pool views ](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/2e08764f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Saba Arawak Hotel

[](https://www.expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information)

Windward Side

8.4/10

Very good

(83 reviews)

"Friendly Staff "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Trilochan

[](https://www.expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information)

![On the beach, scuba diving](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/f062af63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/5cea60f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/e4b10408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/13552485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Old Gin House

[](https://www.expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information)

Oranjestad

8.4/10

Very good

(58 reviews)

"Very awesome hotel, great history and staff was excellent, great job."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael

CA $249

CA $266 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/1d1cb7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/4c62066a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms | Private kitchenette](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/2c07626c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/19000000/18640000/18637300/18637272/f67596c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palm Spring Inn

[](https://www.expedia.ca/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information)

Oranjestad

8.6/10

Excellent

(14 reviews)

"Great place lovely staff"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dameon

CA $156

CA $173 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Oranjestad-Hotels-Palm-Spring-Inn.h18637272.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/499a6edb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/e2cedb25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/7f149889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/cdab380d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Quill Gardens Boutique Hotel

[](https://www.expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information)

Oranjestad

9.6/10

Exceptional

(26 reviews)

"It was great time to stay with comfortable "

![American Samoa](https://a.travel-assets.com/egds/marks/flags/as.svg)

YONG

[](https://www.expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information)

![Premium Bungalow, Non Smoking | Living area](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/ecfb3641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Bungalow, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/1153cce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/638aa03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32820000/32813200/32813162/c48f0519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Talk of the Town Inn & Suites

[](https://www.expedia.ca/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information)

Oranjestad

9.2/10

Wonderful

(13 reviews)

"Great location, nice people, clean."

![Netherlands](https://a.travel-assets.com/egds/marks/flags/nl.svg)

Nadine

CA $148

CA $159 total

includes taxes & fees

Mar 20 - Mar 21

[](https://www.expedia.ca/Oranjestad-Hotels-Talk-Of-The-Town.h32813162.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/23cae97a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/416dcc8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/4e0d4adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/d5b575ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information)

Oranjestad

7.0/10

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](https://a.travel-assets.com/egds/marks/flags/nl.svg)

sytske m.

CA $183

CA $218 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/ed6c9c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment | Living area](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/7b2b7164.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/26c7ebbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment | Terrace/patio](https://images.trvl-media.com/lodging/86000000/85540000/85535700/85535622/6e9f669e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Barrel House St. Eustatius

[](https://www.expedia.ca/Oranjestad-Hotels-Barrel-House-St-Eustatius.h85535622.Hotel-Information)

Oranjestad

8.0/10

Very good

(1 review)

"Ce n’est pas un hôtel, comme indiqué sur Expédia : pas de réception, pas de piscine, mais une simple maison. La propriétaire a « manqué notre réservation » : donc logement pas préparé à notre arrivée. Puis elle parle de vérifier si nous avons réservé la formule avec petit déjeuner, alors qu’Expedia affiche que le petit déjeuner est compris… A noter aussi que la terrasse devant la maison ( côté mer) est celle du restaurant voisin."

![France](https://a.travel-assets.com/egds/marks/flags/fr.svg)

Valérie

[](https://www.expedia.ca/Oranjestad-Hotels-Barrel-House-St-Eustatius.h85535622.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/112b37fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/268182e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/c0dd92a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125410000/125407400/125407386/f1a67479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Oranjestad-Hotels-Spacious-2-Bedroom-Apartment-In-Sint-Eustatius-With-Beautiful-Sunset-Views.h125407386.Hotel-Information)

Sint Eustatius

CA $181

CA $262 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Oranjestad-Hotels-Spacious-2-Bedroom-Apartment-In-Sint-Eustatius-With-Beautiful-Sunset-Views.h125407386.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/c6a9a19c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/a91d2951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/1b2b92a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112810000/112808500/112808442/9e2c7c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic 1-bedroom apartment with AC, WiFi in fabulous Oranjestad

[](https://www.expedia.ca/Oranjestad-Hotels-Chic-1-Bedroom-Apartment-With-AC.h112808442.Hotel-Information)

Oranjestad

CA $183

CA $218 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Oranjestad-Hotels-Chic-1-Bedroom-Apartment-With-AC.h112808442.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22&regionId=11638&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Windward+Side%2C+Saba%2C+Bonaire%2C+Sint+Eustatius+and+Saba&regionId=11638&latLong=17.628452%2C-63.231205&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Windward+Side%2C+Saba%2C+Bonaire%2C+Sint+Eustatius+and+Saba&regionId=11638&latLong=17.628452%2C-63.231205&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=COTTAGE)

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## Top Windward Side Hotel Reviews

![The Old Gin House](https://images.trvl-media.com/lodging/9000000/8280000/8273400/8273394/f062af63_y.jpg)

### The Old Gin House

8/10 Good

"My room has a great view of the ocean and quite comfortable. The room comes with a small refrigerator and a coffee machine. A/C is sound is soft. There is not much of a beach since this is a volcanic island. Location is excellent. Scubaqua is 2 doors down, Barrel House restaurant is next door and Nats Boardwalk is a minute or two walk towards the dock. Old Gin House also has its own restaurant. The path up hill to town is next to the Old Gin House."

[](https://expedia.ca/Oranjestad-Hotels-The-Old-Gin-House.h8273394.Hotel-Information)

![Saba Arawak Hotel](https://images.trvl-media.com/lodging/74000000/73670000/73660700/73660604/d45b92b0_y.jpg)

### Saba Arawak Hotel

10/10 Excellent

"Well organised very clean room, nice balcony. Good wifi. the room had more kitchen equipment than expected, very convenient."

[](https://expedia.ca/Windward-Side-Hotels-Saba-Arawak-Hotel.h73660604.Hotel-Information)

![ Quill Gardens Boutique Hotel](https://images.trvl-media.com/lodging/86000000/85540000/85534600/85534552/499a6edb_y.jpg)

###  Quill Gardens Boutique Hotel

10/10 Excellent

"Great space and wonderful staff "

[](https://expedia.ca/Oranjestad-Hotels-Quill-Gardens-Estate.h85534552.Hotel-Information)

![Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!](https://images.trvl-media.com/lodging/79000000/78390000/78382900/78382857/43320e37_y.jpg)

### Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!

10/10 Excellent

"My husband and I enjoyed a wonderful stay in this comfortable, well situated and historic cottage. Our host, Jeff, was extraordinary, providing an excellent orientation to beautiful Saba and informing us about everything we needed to know to maximize our brief time on the island. His referrals to restaurants and activities were perfect. We look forward to returning as soon as we can!"

[](https://expedia.ca/Windward-Side-Hotels-Historic-Saban-Cottage-In-Windwardside.h78382857.Hotel-Information)

![Flamboyant Cottage - Spectacular View & Pool](https://images.trvl-media.com/lodging/35000000/34010000/34006200/34006194/cbfa65db_y.jpg)

### Flamboyant Cottage - Spectacular View & Pool

10/10 Excellent

"Lovely cabin with incredible view. "

[](https://expedia.ca/Windward-Side-Hotels-Beautiful-Gingerbread-Cottage-Spectacular-View-Pool.h34006194.Hotel-Information)

![Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad](https://images.trvl-media.com/lodging/118000000/117520000/117519900/117519865/23cae97a_y.jpg)

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

6/10 Okay

"The staff was ok but they came late to open for me. While the property was generally up to standards there was not toilet tissue neither bathing soap. Did not.know i had to provide these myself."

[](https://expedia.ca/Oranjestad-Hotels-Charming-1-Bedroom-Apartment-With-AC.h117519865.Hotel-Information)

![El Momo Cottages](https://images.trvl-media.com/lodging/12000000/11950000/11944600/11944556/59c43c6c_y.jpg)

### El Momo Cottages

10/10 Excellent

"The staff is fantastic! Cabins are simple, clean and comfortable. Breakfast was delicious.The views are amazing! Be prepared to climb to enjoy the views. Lots of stairs but worth it!"

[](https://expedia.ca/Windward-Side-Hotels-El-Momo-Cottages.h11944556.Hotel-Information)

![Peter Hytte is close to everything at great price!](https://images.trvl-media.com/lodging/90000000/89690000/89687400/89687379/c3956cf7_y.jpg)

### Peter Hytte is close to everything at great price!

10/10 Excellent

"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?"

[](https://expedia.ca/Windward-Side-Hotels-Peter-Hytte-Is-Close-To-Everything-At-Great-Price.h89687379.Hotel-Information)

![Home a way from home in the Unspoiled queen of the Caribbean.](https://images.trvl-media.com/lodging/74000000/73240000/73234400/73234367/762dffce_y.jpg)

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

10/10 Excellent

"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."

[](https://expedia.ca/Windward-Side-Hotels-Home-A-Way-From-Home-In-The-Unspoiled-Queen-Of-The-Caribbean.h73234367.Hotel-Information)

## Find out more about Windward Side

## Windward Side Vacation Homes information

| Number of reviews | 184              |
| ----------------- | ---------------- |
| Accommodation     | 2 Vacation Homes |
| Lowest Price      | CA $159          |
| Highest Price     | CA $266          |