Windward Vacation Rentals with Pools
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)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£971/Night
7 Nights - £6,797
Villa
10.0(39 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
£309/Night
7 Nights - £2,166
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(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
£859/Night
7 Nights - £6,014
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(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
Hot Tub- Pool
- Balcony/Terrace
£570/Night
7 Nights - £3,988
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(27 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
Pet Friendly
£606/Night
7 Nights - £4,241
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
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 Jelo - 3 bdr - 2.5 bth - Pool & SPA - Games Room
- Modern Villa Suite Acajous Boasts Splendid Views !
- Villa 'Coco de Mer' Breathtaking views over St. Jean, Eden Rock & nearby Islands
- Villa La Magnifica | Ocean View - Located in Beautiful Deve with Private 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 Vue
- Villa La Magnifica | Ocean View - Located in Magnificent Deve 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 3363 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
Villa
9.3(40 Reviews)
13 Bedrooms
13 Baths
26 Guests
1453.13 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£360/Night
7 Nights - £2,522
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
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
Villa
10.0(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£298/Night
7 Nights - £2,089
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£2,577/Night
7 Nights - £18,041
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
6 Guests
2153 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£2,577/Night
7 Nights - £18,041
Villa
10.0(15 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
£647/Night
7 Nights - £4,526
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£696/Night
7 Nights - £4,874
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,816/Night
7 Nights - £12,709
Villa
10.0(11 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,058/Night
7 Nights - £7,406
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£918/Night
7 Nights - £6,426
