Windward Short Term Stay
Villa
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
Private Pool
Oceanfront
Pool
Ocean View
US $870/Night
7 Nights - US $6,091
Villa
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $692/Night
7 Nights - US $4,843
Villa
8.6(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
Kitchen
Parking
US $1,153/Night
7 Nights - US $8,074
Villa
1 Bedroom
1 Bath
1 Guest
- Private Pool
- Pool
Balcony/Terrace- Kitchen
US $636/Night
7 Nights - US $4,455
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1475 ft²
- Private Pool
Fireplace/Heating- Pool
Pet Friendly
US $775/Night
7 Nights - US $5,426
Villa
9.6(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
Hot Tub
Spa
US $1,013/Night
7 Nights - US $7,093
Villa
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
- Kitchen
Air Conditioner
US $2,305/Night
7 Nights - US $16,135
Villa
1 Bedroom
2 Baths
4 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $853/Night
7 Nights - US $5,973
Cottage
10.0(101 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $451/Night
7 Nights - US $3,155
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
US $2,287/Night
7 Nights - US $16,012
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $624/Night
7 Nights - US $4,371
People Visiting Windward Also Like
Why Choose Rent By Owner for your Windward Short Term Stay?
What makes our Short Term 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 Short Term Stay
What's our booking process?
Our platform allows you to browse a curated selection of short term 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 Short Term Stay Amenities
What amenities can you expect?
Our Short Term 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
Petit Cul-de-Sac
Camaruche
Gouverneur
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Frequently Asked Questions About Windward Short-term Rentals
1. What are the top Short Term 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 Short Term Stays in Windward:
- Fabulous stay in modern Villa – Surrounded by nature. Special Offer
- Hotel Les Ondines Sur La Plage
- BOUGAINVILLIERS Very Private and Charming Villa With Sea View Close to the Beach
- Villa Whalhalla-4 bed-4 bath-POINTE MILOU
- 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.
- Green Lagoon, sea views, direct owner, credit cards, 2 or 3 bedroomss rate
2. How many Short Term Stays are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 8 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Short Term Stays in Windward.
More Rentals You May Like Near Windward
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $1,410/Night
7 Nights - US $9,870
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,280/Night
7 Nights - US $8,962
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,318/Night
7 Nights - US $9,226
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $918/Night
7 Nights - US $6,424
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $943/Night
7 Nights - US $6,600
Villa
10.0(27 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,748/Night
7 Nights - US $12,234
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,083/Night
7 Nights - US $21,580
Villa
9.7(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
75.35 ft²
- Balcony/Terrace
View- Parking
- Air Conditioner
US $899/Night
7 Nights - US $6,290
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $271/Night
7 Nights - US $1,897
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $1,171/Night
7 Nights - US $8,196
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $2,815/Night
7 Nights - US $19,707
