1. St. Barthelemy
  2. Windward
  3. Monthly Stay

Windward Monthly Stay

10.0
Exceptional
(1 Review)
8 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Villa
  • Private Pool
  • Pool
  • Balcony/Terrace
AU $5,093/Night For 7 Nights AU $35,652
10.0
Exceptional
(2 Reviews)
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
10.0
Exceptional
(1 Review)
4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Private Pool
  • Pool
  • Kitchen
AU $2,548/Night For 7 Nights AU $17,837
9.6
Exceptional
(8 Reviews)
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
10.0
Exceptional
(1 Review)
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
9.0
Exceptional
(42 Reviews)
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
New
13455 ft² 20 Guests 10 Bedrooms 10 Bathrooms
Family Friendly Villa
  • Private Pool
  • Pool
  • Balcony/Terrace
Unlock the Best Price
9.0
Exceptional
(31 Reviews)
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
New
5920 ft² 12 Guests 6 Bedrooms 6 Bathrooms
Family Friendly Villa
  • Private Pool
  • Hot Tub
  • Pool
Unlock the Best Price
7.9
Very Good
(14 Reviews)
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
New
10 Guests 5 Bedrooms 5 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Hot Tub
AU $12,477/Night For 7 Nights AU $87,336
New
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?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Windward

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.

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
Barriere des Quatres Vents
Grand Cul-de-Sac
Petit Cul-de-Sac
Morne de Depoudre
Grand Cul de Sac

Frequently Asked Questions About Windward Monthly Stays

1. What are 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 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

New
8 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Villa
  • Private Pool
  • Pool
  • Balcony/Terrace
AU $11,011/Night For 7 Nights AU $77,076
New
8 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Villa
  • Pool
  • Kitchen
  • Air Conditioner
AU $9,333/Night For 7 Nights AU $65,332
New
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
New
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
New
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
New
8 Guests 4 Bedrooms 4 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Pool
AU $4,986/Night For 7 Nights AU $34,903
New
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
New
6 Guests 3 Bedrooms 5 Bathrooms
Family Friendly Villa
  • Pool
  • Balcony/Terrace
  • Kitchen
AU $4,413/Night For 7 Nights AU $30,892
New
6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Pool
AU $4,273/Night For 7 Nights AU $29,913
New
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
New
6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Villa
  • Pool
  • Ocean View
  • Balcony/Terrace
AU $3,905/Night For 7 Nights AU $27,333
New
6 Guests 3 Bedrooms 3 Bathrooms
Family Friendly Villa
  • Private Pool
  • Pool
  • Balcony/Terrace
AU $3,873/Night For 7 Nights AU $27,108