Windward Vacation Rentals with Pools
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 $611/Night
7 Nights - US $4,275
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(39 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $473/Night
7 Nights - US $3,314
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(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,274/Night
7 Nights - US $8,921
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
Pet Friendly
US $913/Night
7 Nights - US $6,390
Apartment
9.6(19 Reviews)
1 Bedroom
1 Bath
2 Guests
64.58 ft²
- Pool
- Balcony/Terrace
View
Parking
US $261/Night
7 Nights - US $1,827
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
Hot Tub- Pool
- Balcony/Terrace
US $1,175/Night
7 Nights - US $8,226
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
Anse de Toiny
Grand Cul-de-Sac
Barriere des Quatres Vents
Camaruche
Mont Morne de Vitet
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Petit 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:
- Please Inquire Before Booking – Luxury Villa
- Villa La Maison Rouge (3 bedrooms)
- Please Inquire Before Booking – Luxury Villa
- Eden House (1/3 Rooms)
- Villa Agave Azul (4 bedrooms)
- Villa Upside (3 bedrooms)
- Villa Ti Rock (1 bedroom)
- Please Inquire Before Booking – Luxury Villa
- Villa Valley (2 bedrooms)
- Please Inquire Before Booking – Luxury Villa
2. How many Rentals With Pools are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 3325 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
House
9.6(8 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $191/Night
7 Nights - US $1,334
Villa
10.0(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $442/Night
7 Nights - US $3,096
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $2,802/Night
7 Nights - US $19,617
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,045/Night
7 Nights - US $7,315
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)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $970/Night
7 Nights - US $6,792
Villa
10.0(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1615 ft²
- Pool
- Kitchen
Air Conditioner
Internet
US $874/Night
7 Nights - US $6,119
Villa
10.0(5 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,494/Night
7 Nights - US $24,457
Villa
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
1561 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,313/Night
7 Nights - US $9,189
Villa
10.0(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
2906 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,246/Night
7 Nights - US $8,722
Villa
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
754 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $474/Night
7 Nights - US $3,317
Villa
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,654/Night
7 Nights - US $11,575
