Windward Cottage Rentals
Cottage
10.0(101 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Pool
Ocean View
Balcony/Terrace
R6,456/Night
7 Nights - R45,192
Cottage
2 Bedrooms
1 Bath
4 Guests
538 ft²
Oceanfront- Ocean View
- Balcony/Terrace
View
R5,207/Night
7 Nights - R36,458
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
R10,077/Night
7 Nights - R70,534
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R11,225/Night
7 Nights - R78,573
R37,837/Night
7 Nights - R264,866
Villa
10.0(39 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R6,948/Night
7 Nights - R48,633
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
R23,324/Night
7 Nights - R163,267
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R19,238/Night
7 Nights - R134,666
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R21,801/Night
7 Nights - R152,614
Villa
10.0(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
R12,792/Night
7 Nights - R89,540
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R15,595/Night
7 Nights - R109,175
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
Pet Friendly
R13,568/Night
7 Nights - R94,983
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.
Explore and book the perfect rental in Windward
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
Barriere des Quatres Vents
Anse de Toiny
Petit Cul-de-Sac
Camaruche
Gouverneur
Morne de Depoudre
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 Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View
- Villa Whalhalla-4 bed-4 bath-POINTE MILOU
- Sea view, very private
- Villa Tiwa 2 Bed-2 Bath Pointe Milou
- Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
- Blue Lagoon Villa, 4 to 7 bedrooms and 1 pool
- grand appartement, vue ocean
- Amazing swimming pool. La Roche dans l'Eau.
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
9.7(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
75.35 ft²
- Balcony/Terrace
- View
Parking
Air Conditioner
R14,864/Night
7 Nights - R104,048
Villa
10.0(26 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R33,170/Night
7 Nights - R232,196
Apartment
9.6(19 Reviews)
1 Bedroom
1 Bath
2 Guests
64.58 ft²
- Pool
- Balcony/Terrace
- View
- Parking
R4,317/Night
7 Nights - R30,222
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R57,714/Night
7 Nights - R403,999
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
R3,868/Night
7 Nights - R27,079
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
R17,537/Night
7 Nights - R122,756
Villa
10.0(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R6,683/Night
7 Nights - R46,780
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R57,714/Night
7 Nights - R403,999
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R57,714/Night
7 Nights - R403,999
Villa
10.0(15 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
R14,479/Night
7 Nights - R101,351
House
10.0(15 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R4,090/Night
7 Nights - R28,634
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R15,593/Night
7 Nights - R109,142
