Cottage
10.0(103 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Parking
Pool
Ocean View
R7,316/Night
7 Nights - R51,204
Windward Cottage Rentals
10.0
Cottage
2 Bedrooms
1 Bath
4 Guests
538 ft²
Oceanfront- Parking
- Ocean View
Balcony/Terrace
R5,715/Night
7 Nights - R40,008
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R11,195/Night
7 Nights - R78,375
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
R7,747/Night
7 Nights - R54,227
R37,170/Night
7 Nights - R260,199
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R15,256/Night
7 Nights - R106,796
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
Hot Tub- Parking
- Ocean View
R15,279/Night
7 Nights - R106,959
Villa
10.0(27 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
Breakfast
R37,265/Night
7 Nights - R260,865
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
R21,417/Night
7 Nights - R149,925
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
R4,488/Night
7 Nights - R31,412
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
R19,703/Night
7 Nights - R137,916
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
R19,181/Night
7 Nights - R134,276
People Visiting Windward Also Like
Why Choose Rent By Owner for your Windward Cottage Rentals?
What makes our Cottage Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windward
How to Book Your Windward Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Windward
Quartier Lorient
Morne Criquet
Pointe Milou
Grand Cul-de-Sac
Anse de Toiny
Barriere des Quatres Vents
Gouverneur
Camaruche
Petit Cul-de-Sac
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Frequently Asked Questions About Windward Rental Cottages
1. What are the top Cottages in Windward?
There are a lot of options in Windward. If you plan on staying in the Windward area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Windward:
- Hotel Les Ondines Sur La Plage
- BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
- Villa Tiwa 2 Bed-2 Bath Pointe Milou
- Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
- grand appartement, vue ocean
- Amazing swimming pool. La Roche dans l'Eau.
- Lagon Jaune, amazing sea view, direct owner, credit card, 3 or 4 bedrooms rate
- Bungalow CAZ A Saline N°2
- Villa Roy - Lagoon & Ocean Breathtaking View
- Villa Anakao - Great Central Location
2. How many Cottages are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 2 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Windward.
More Rentals You May Like Near Windward
Villa
9.8(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
75.35 ft²
- Parking
- Balcony/Terrace
- View
Air Conditioner
R16,086/Night
7 Nights - R112,598
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
R17,999/Night
7 Nights - R125,988
House
10.0(15 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
R3,989/Night
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Villa
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
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- Parking
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R28,794/Night
7 Nights - R201,551
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Parking
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R17,313/Night
7 Nights - R121,194
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R50,307/Night
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Villa
10.0(11 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R16,086/Night
7 Nights - R112,598
Villa
10.0(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
1475 ft²
- Private Pool
- Parking
- Pool
- Kitchen
R13,358/Night
7 Nights - R93,504
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
R20,927/Night
7 Nights - R146,496
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
R20,228/Night
7 Nights - R141,588
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
R16,076/Night
7 Nights - R112,533
