Windward Monthly Stay
New
Villa
5 Bedrooms
5 Baths
10 Guests
20000 ft²
Private Pool
Oceanfront
Pool
Ocean View
US $6,160/Night
7 Nights - US $43,118
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
US $679/Night
7 Nights - US $4,750
New
Villa
7 Bedrooms
7 Baths
14 Guests
10000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $5,342/Night
7 Nights - US $37,395
House
9.6(8 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $191/Night
7 Nights - US $1,334
New
Villa
5 Bedrooms
5 Baths
10 Guests
3000 ft²
- Private Pool
- Oceanfront
Hot Tub- Pool
US $4,300/Night
7 Nights - US $30,098
Villa
9.3(40 Reviews)
13 Bedrooms
13 Baths
26 Guests
1453.13 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $489/Night
7 Nights - US $3,423
Villa
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,848/Night
7 Nights - US $26,936
Apartment
9.0(31 Reviews)
1 Bedroom
1 Bath
2 Guests
505.9 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
US $287/Night
7 Nights - US $2,008
New
Villa
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $3,726/Night
7 Nights - US $26,084
Apartment
7.9(30 Reviews)
1 Bedroom
1 Bath
2 Guests
430.56 ft²
- Pool
- Balcony/Terrace
Pet Friendly
Parking
US $304/Night
7 Nights - US $2,127
Villa
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,358/Night
7 Nights - US $23,508
House
7.9(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
645.83 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $434/Night
7 Nights - US $3,036
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
Anse de Toiny
Grand Cul-de-Sac
Barriere des Quatres Vents
Camaruche
Mont Morne de Vitet
Petit Cul-de-Sac
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Windward Monthly Stay Frequently Asked Questions
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:
2. How many Monthly Stays are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 131 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
Villa
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $2,752/Night
7 Nights - US $19,262
Villa
3 Bedrooms
3 Baths
6 Guests
4306 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
US $2,305/Night
7 Nights - US $16,137
Villa
1 Bedroom
1 Bath
2 Guests
- Private Pool
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US $2,242/Night
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New
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4 Bedrooms
4 Baths
8 Guests
4000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $2,004/Night
7 Nights - US $14,026
US $1,721/Night
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Villa
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,607/Night
7 Nights - US $11,248
US $1,588/Night
7 Nights - US $11,115
Villa
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,588/Night
7 Nights - US $11,115
Villa
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,553/Night
7 Nights - US $10,873
US $1,533/Night
7 Nights - US $10,733
US $1,454/Night
7 Nights - US $10,179
Villa
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,370/Night
7 Nights - US $9,587
