Windward Pet Friendly Vacation Rentals
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
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(1 Review)
1 Bedroom
1 Bath
- Pet Friendly
Air Conditioner
Internet
Child Friendly
US $1,467/Night
7 Nights - US $10,266
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(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(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
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(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
US $1,365/Night
7 Nights - US $9,555
Resort
9.5(2 Reviews)
31 Baths
75 Guests
850.89 ft²
Private Beach- Oceanfront
- Hot Tub
Spa
US $1,357/Night
7 Nights - US $9,502
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
9.3(40 Reviews)
13 Bedrooms
13 Baths
26 Guests
1453.13 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $489/Night
7 Nights - US $3,423
Villa
9.8(25 Reviews)
5 Bedrooms
5 Baths
10 Guests
7535 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $4,492/Night
7 Nights - US $31,447
Why Choose Rent By Owner for your Windward Pet Friendly Vacation Rentals?
What makes our Pet Friendly Vacation Rentals 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 Pet Friendly Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of pet friendly vacation rentals. 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 Pet Friendly Vacation Rentals Amenities
What amenities can you expect?
Our Pet Friendly Vacation Rentals 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 Pet-Friendly Rentals
1. What are the top Pet Friendly Rentals 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 Pet Friendly Rentals in Windward:
2. How many Pet Friendly Rentals are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 418 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Pet Friendly Rentals in Windward.
More Rentals You May Like Near Windward
Apartment
9.3(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
645.83 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
US $296/Night
7 Nights - US $2,072
Apartment
9.6(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $486/Night
7 Nights - US $3,405
Villa
9.6(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
1938 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $375/Night
7 Nights - US $2,627
Villa
9.4(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,367/Night
7 Nights - US $9,570
Villa
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $2,965/Night
7 Nights - US $20,753
Villa
4 Bedrooms
4 Baths
8 Guests
- Oceanfront
- Ocean View
- View
- Pet Friendly
US $2,707/Night
7 Nights - US $18,948
Villa
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
Breakfast
US $2,041/Night
7 Nights - US $14,284
Villa
3 Bedrooms
2 Baths
6 Guests
1292 ft²
- Pool
- Pet Friendly
Kitchen
Parking
US $1,867/Night
7 Nights - US $13,067
Villa
1 Bedroom
2 Baths
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,700/Night
7 Nights - US $11,897
Villa
4 Bedrooms
3 Baths
7 Guests
- Balcony/Terrace
- Breakfast
- Pet Friendly
- Kitchen
US $1,422/Night
7 Nights - US $9,952
Villa
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,303/Night
7 Nights - US $9,124
Villa
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,243/Night
7 Nights - US $8,701
