Windward Holiday Homes
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
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
Why Choose Rent By Owner for your Windward Holiday Homes?
What makes our Holiday Homes 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 Holiday Homes
What's our booking process?
Our platform allows you to browse a curated selection of holiday homes. 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 Holiday Homes Amenities
What amenities can you expect?
Our Holiday Homes 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
Barriere des Quatres Vents
Grand Cul-de-Sac
Petit Cul-de-Sac
Camaruche
Gouverneur
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Windward Holiday Homes Frequently Asked Questions
1. What are the top Holiday Homes 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 Holiday Homes in Windward:
- Modern Villa Suite Acajous Boasts Splendid Views !
- Villa La Magnifica | Ocean View - Located in Beautiful Deve with Private Pool
- Villa 'Coco de Mer' Breathtaking views over St. Jean, Eden Rock & nearby Islands
- Villa Endeavour So private, breathtaking ocean views, direct from owner !
- Villa Yvantino beachfront (2 bedroom)
- Villa Caco (3 bedrooms)
- Villa La Vue
- Villa La Magnifica | Ocean View - Located in Magnificent Deve with Private Pool
- Beach 2 minutes' walk, private deck, tranquility
- Villa Samsara | Ocean View - Located in Wonderful Pointe Milou with Private Pool
2. How many Holiday Homes are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 3557 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Windward.
More Rentals You May Like Near Windward
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
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $857/Night
7 Nights - US $5,999
Villa
10.0(15 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $975/Night
7 Nights - US $6,823
House
10.0(15 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $271/Night
7 Nights - US $1,894
Villa
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,578/Night
7 Nights - US $11,046
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,050/Night
7 Nights - US $7,348
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,096/Night
7 Nights - US $21,670
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $1,039/Night
7 Nights - US $7,272
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,038/Night
7 Nights - US $7,263
