Windward Vacation Rentals with Pools
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Pool
- Ocean View
US $537/Night
For 7 Nights US $3,762
753.47 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
US $679/Night
For 7 Nights US $4,750
1 Bedroom
1 Bathroom
Ocean View
Hotel
- Pool
- Ocean View
- Balcony/Terrace
US $2,287/Night
For 7 Nights US $16,012
1399 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $677/Night
For 7 Nights US $4,739
2152.78 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
Villa
- Oceanfront
- Pool
- Ocean View
US $1,318/Night
For 7 Nights US $9,226
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $420/Night
For 7 Nights US $2,940
64.58 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Pool
- Balcony/Terrace
- View
US $261/Night
For 7 Nights US $1,827
7000 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $1,088/Night
For 7 Nights US $7,619
645.83 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Pool
- Ocean View
US $191/Night
For 7 Nights US $1,334
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
US $806/Night
For 7 Nights US $5,645
850.89 ft²
75 Guests
66 Bedrooms
31 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Hot Tub
US $1,357/Night
For 7 Nights US $9,502
3500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $827/Night
For 7 Nights US $5,790
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
Barriere des Quatres Vents
Anse de Toiny
Grand Cul-de-Sac
Petit Cul-de-Sac
Gouverneur
Camaruche
Morne de Depoudre
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 'Coco de Mer' Fabulous views of St Jean Bay and Eden Rock
- Villa La Magnifica | Ocean View - Located in Beautiful Deve with Private Pool
- Villa Jelo - 3 bdr - 2.5 bth - Pool & SPA - Games Room
- THE VILLA AFRICAN QUEEN - AN OASIS IN THE CARIBBEANS WITH A GIANT POOL !
- Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view
- Villa Endeavour So private, breathtaking ocean views, direct from owner !
- Villa Caco (3 bedrooms)
- Villa Angelique - Luxury 4 Bedroom Villa with Private Pool - St Barts
- Villa La Magnifica | Ocean View - Located in Magnificent Deve with Private Pool
- Villa Samsara | Ocean View - Located in Wonderful Pointe Milou 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 3345 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
322.92 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Pool
- Ocean View
US $287/Night
For 7 Nights US $2,009
3229 ft²
10 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $5,795/Night
For 7 Nights US $40,563
3000 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
US $2,411/Night
For 7 Nights US $16,874
1507 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
US $1,044/Night
For 7 Nights US $7,310
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $538/Night
For 7 Nights US $3,766
3229 ft²
14 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $3,477/Night
For 7 Nights US $24,338
2153 ft²
6 Guests
7 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $3,477/Night
For 7 Nights US $24,338
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Pool
US $872/Night
For 7 Nights US $6,106
20451 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $939/Night
For 7 Nights US $6,575
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $2,464/Night
For 7 Nights US $17,251
2150 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
US $1,415/Night
For 7 Nights US $9,905
1 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Hot Tub
- Pool
US $872/Night
For 7 Nights US $6,106
