Windward Monthly Stay
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
AU $5,093/Night
For 7 Nights AU $35,652
753.47 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
AU $946/Night
For 7 Nights AU $6,625
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Kitchen
AU $2,548/Night
For 7 Nights AU $17,837
645.83 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Pool
- Ocean View
AU $266/Night
For 7 Nights AU $1,861
807 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
AU $1,061/Night
For 7 Nights AU $7,428
1453.13 ft²
26 Guests
13 Bedrooms
13 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
AU $682/Night
For 7 Nights AU $4,774
13455 ft²
20 Guests
10 Bedrooms
10 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
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505.9 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Ocean View
- Balcony/Terrace
AU $400/Night
For 7 Nights AU $2,801
5920 ft²
12 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
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645.83 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
AU $605/Night
For 7 Nights AU $4,234
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
AU $12,477/Night
For 7 Nights AU $87,336
2152.78 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Pool
AU $5,049/Night
For 7 Nights AU $35,341
Why Choose Rent By Owner for your Windward Monthly Stay?
What makes our Monthly Stay 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 Monthly Stay
What's our booking process?
Our platform allows you to browse a curated selection of monthly stay. 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 Monthly Stay Amenities
What amenities can you expect?
Our Monthly Stay 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
Barriere des Quatres Vents
Anse de Toiny
Grand Cul-de-Sac
Petit Cul-de-Sac
Gouverneur
Camaruche
Morne de Depoudre
Grand Cul de Sac
Frequently Asked Questions About Windward Monthly Stays
1. What are the top Monthly Stays 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 Monthly Stays in Windward:
- Exclusive Island Retreat
- Villa Laeti
- Villa Essenia - Vue Lagon avec Piscine
- Krystel (2/4 Rooms) Luxury villa
- Villa Les Basses by Fantasia Villas
- Krystel (1/4 Rooms) Luxury villa
- Exceptional villa with pool and spa, Saint-Barthélemy.
- Please Inquire Before Booking – Luxury Villa
- Beautiful Samsara Luxury villa
- Villa Claire by Fantasia Villas
2. How many Monthly Stays are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 124 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Monthly Stays in Windward.
More Rentals You May Like Near Windward
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
AU $11,011/Night
For 7 Nights AU $77,076
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Pool
- Kitchen
- Air Conditioner
AU $9,333/Night
For 7 Nights AU $65,332
4306 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
AU $8,120/Night
For 7 Nights AU $56,842
4000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
AU $7,457/Night
For 7 Nights AU $52,197
3000 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
AU $5,685/Night
For 7 Nights AU $39,796
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
AU $4,986/Night
For 7 Nights AU $34,903
3000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
AU $4,955/Night
For 7 Nights AU $34,683
6 Guests
3 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Kitchen
AU $4,413/Night
For 7 Nights AU $30,892
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
AU $4,273/Night
For 7 Nights AU $29,913
3000 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
AU $4,223/Night
For 7 Nights AU $29,559
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Pool
- Ocean View
- Balcony/Terrace
AU $3,905/Night
For 7 Nights AU $27,333
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
AU $3,873/Night
For 7 Nights AU $27,108
