Windward Vacation Rentals with Pools
Cottage
10.0(102 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Parking
Pool
Ocean View
AU $647/Night
7 Nights - AU $4,530
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
Oceanfront- Parking
- Pool
- Ocean View
AU $681/Night
7 Nights - AU $4,768
AU $3,268/Night
7 Nights - AU $22,879
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Parking
- Pool
Balcony/Terrace
AU $892/Night
7 Nights - AU $6,246
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
Breakfast- Parking
- Pool
AU $1,883/Night
7 Nights - AU $13,183
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
AU $1,829/Night
7 Nights - AU $12,806
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
AU $1,347/Night
7 Nights - AU $9,431
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
AU $1,318/Night
7 Nights - AU $9,225
Villa
10.0(27 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
Hot Tub- Breakfast
AU $2,501/Night
7 Nights - AU $17,508
Apartment
9.6(19 Reviews)
1 Bedroom
1 Bath
2 Guests
64.58 ft²
- Parking
- Pool
- Balcony/Terrace
View
AU $373/Night
7 Nights - AU $2,611
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
AU $4,005/Night
7 Nights - AU $28,035
Why Choose Rent By Owner for your Windward Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools 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 Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. 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 Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools 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
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Frequently Asked Questions About Windward Rentals with Pools
1. What are the top Rentals With Pools 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 Rentals With Pools in Windward:
- Villa La Magnifica | Ocean View - Located in Beautiful Deve with Private Pool
- Villa Endeavour So private, breathtaking ocean views, direct from owner !
- Villa Caco (3 bedrooms)
- Villa La Vue
- Villa La Magnifica | Ocean View - Located in Magnificent Deve with Private Pool
- NEW, INTIMATE BUNGALOW WITH POOL
- Appartement St Jean, Saint-barthélemy
- Beach 2 minutes' walk, private deck, tranquility
- Villa Samsara | Ocean View - Located in Wonderful Pointe Milou with Private Pool
- Villa Costa Nova | Ocean View - Located in Stunning Gouverneur with Private Pool
2. How many Rentals With Pools are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 3346 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Windward.
More Rentals You May Like Near Windward
Resort
9.6(8 Reviews)
20 Baths
75 Guests
850.89 ft²
Private Beach- Oceanfront
- Hot Tub
- Breakfast
AU $1,940/Night
7 Nights - AU $13,577
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
AU $1,673/Night
7 Nights - AU $11,711
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
AU $4,023/Night
7 Nights - AU $28,159
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
AU $1,225/Night
7 Nights - AU $8,572
Villa
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $2,255/Night
7 Nights - AU $15,784
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $1,500/Night
7 Nights - AU $10,500
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
AU $4,423/Night
7 Nights - AU $30,964
Villa
10.0(11 Reviews)
2 Bedrooms
3 Baths
4 Guests
2153 ft²
- Parking
- Pool
- Balcony/Terrace
Kitchen
AU $1,243/Night
7 Nights - AU $8,702
Villa
10.0(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
1475 ft²
- Private Pool
- Parking
- Pool
- Kitchen
AU $1,218/Night
7 Nights - AU $8,528
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
AU $1,609/Night
7 Nights - AU $11,264
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
AU $1,539/Night
7 Nights - AU $10,775
Villa
10.0(10 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $1,393/Night
7 Nights - AU $9,749
