Windward Short Term Stay
Villa
10.0(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1475 ft²
Private Pool
Fireplace/Heating
Pool
Pet Friendly
£568/Night
7 Nights - £3,972
Villa
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
Oceanfront- Pool
Ocean View
£575/Night
7 Nights - £4,027
Villa
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£458/Night
7 Nights - £3,202
Villa
1 Bedroom
1 Bath
1 Guest
- Private Pool
- Pool
Balcony/Terrace
Kitchen
£476/Night
7 Nights - £3,330
Villa
9.6(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
Hot Tub
Spa
£746/Night
7 Nights - £5,225
Villa
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
- Kitchen
Air Conditioner
£1,698/Night
7 Nights - £11,887
Villa
1 Bedroom
2 Baths
4 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
£629/Night
7 Nights - £4,400
Cottage
10.0(98 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£295/Night
7 Nights - £2,066
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£500/Night
7 Nights - £3,499
£1,685/Night
7 Nights - £11,796
Villa
10.0(54 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
£452/Night
7 Nights - £3,165
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
£1,039/Night
7 Nights - £7,271
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
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 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 Kali - Villa for 2 - Pool, Wi-Fi, Spectacular View
- Villa Whalhalla-4 bed-4 bath-POINTE MILOU
- Sea view, very private
- Villa Tiwa 2 Bed-2 Bath Pointe Milou
- Blue Lagoon Villa, 4 to 7 bedrooms and 1 pool
- Spacious Luxury 4 bedrooms, direct no agencies, fully renovated
- grand appartement, vue ocean
2. How many Short Term Stays are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 7 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(39 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
£309/Night
7 Nights - £2,166
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£971/Night
7 Nights - £6,797
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
£859/Night
7 Nights - £6,014
Apartment
9.6(19 Reviews)
1 Bedroom
1 Bath
2 Guests
64.58 ft²
- Pool
- Balcony/Terrace
View
Parking
£192/Night
7 Nights - £1,346
Villa
10.0(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
£570/Night
7 Nights - £3,988
House
9.6(8 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£140/Night
7 Nights - £983
Villa
10.0(27 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
£606/Night
7 Nights - £4,241
Resort
9.5(2 Reviews)
31 Baths
75 Guests
850.89 ft²
Private Beach- Oceanfront
- Hot Tub
- Spa
£1,000/Night
7 Nights - £7,000
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
10 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£2,577/Night
7 Nights - £18,041
Villa
10.0(25 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£1,481/Night
7 Nights - £10,368
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
£172/Night
7 Nights - £1,206
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
£783/Night
7 Nights - £5,482
