Windward Monthly Stay
Villa
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
Pool
Balcony/Terrace
Breakfast
Pet Friendly
CA $4,959/Night
7 Nights - CA $34,711
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
Oceanfront- Pool
Ocean View- Balcony/Terrace
CA $929/Night
7 Nights - CA $6,502
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
Private Pool- Pool
Kitchen
Parking
CA $1,286/Night
7 Nights - CA $9,000
House
9.6(8 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $261/Night
7 Nights - CA $1,826
Villa
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $839/Night
7 Nights - CA $5,870
Villa
9.3(40 Reviews)
13 Bedrooms
13 Baths
26 Guests
1453.13 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $669/Night
7 Nights - CA $4,685
Villa
10 Bedrooms
10 Baths
20 Guests
13455 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
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Apartment
9.0(31 Reviews)
1 Bedroom
1 Bath
2 Guests
505.9 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
CA $393/Night
7 Nights - CA $2,749
Villa
6 Bedrooms
6 Baths
12 Guests
5920 ft²
- Private Pool
Hot Tub- Pool
- Balcony/Terrace
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Apartment
7.9(30 Reviews)
1 Bedroom
1 Bath
2 Guests
430.56 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
CA $421/Night
7 Nights - CA $2,943
Villa
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
Fireplace/Heating
CA $10,037/Night
7 Nights - CA $70,256
House
7.9(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
645.83 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $594/Night
7 Nights - CA $4,156
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
Grand Cul-de-Sac
Anse de Toiny
Barriere des Quatres Vents
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 Tycia
- Charming villa with Outstanding View
- Please Inquire Before Booking – Luxury Villa
- Villa Laeti
- Villa Essenia - Vue Lagon avec Piscine
- Krystel (2/4 Rooms) Luxury villa
- Lurin's Finest Villa Close to Gustavia
- LA CORNICHE by WIMCO St. Barth Properties
- Krystel (1/4 Rooms) Luxury villa
2. How many Monthly Stays are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 130 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
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5 Bedrooms
5 Baths
10 Guests
5000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
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8 Guests
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Villa
4 Bedrooms
4 Baths
8 Guests
- Pool
- Kitchen
Air Conditioner
Internet
CA $5,351/Night
7 Nights - CA $37,455
Villa
5 Bedrooms
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10 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
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CA $5,349/Night
7 Nights - CA $37,445
Villa
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,894/Night
7 Nights - CA $34,256
Villa
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
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CA $4,655/Night
7 Nights - CA $32,586
Villa
4 Bedrooms
4 Baths
8 Guests
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- Private Pool
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- Hot Tub
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CA $4,655/Night
7 Nights - CA $32,586
Villa
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6 Guests
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7 Nights - CA $29,358
New
Villa
3 Bedrooms
5 Baths
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $4,089/Night
7 Nights - CA $28,626
