Windward Islands Winter Rental
2583 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
CA $2,090/Night
For 7 Nights CA $14,630
430.56 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $360/Night
For 7 Nights CA $2,520
CA $745/Night
For 7 Nights CA $5,212
646 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Pool
CA $511/Night
For 7 Nights CA $3,580
4359.38 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Spa
CA $884/Night
For 7 Nights CA $6,190
484 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $147/Night
For 7 Nights CA $1,027
1356.25 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Spa
- Pool
CA $385/Night
For 7 Nights CA $2,695
3983 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $1,451/Night
For 7 Nights CA $10,158
452.08 ft²
3 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Oceanfront
- Hot Tub
- Spa
CA $306/Night
For 7 Nights CA $2,141
1722 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
CA $586/Night
For 7 Nights CA $4,102
1506.95 ft²
12 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Ski Chalet
- Balcony/Terrace
- Pet Friendly
- Parking
CA $190/Night
For 7 Nights CA $1,332
807 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Private Pool
- Pool
- Ocean View
CA $304/Night
For 7 Nights CA $2,126
Why Choose Rent By Owner for your Windward Islands Winter Rental?
What makes our Winter Rental 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 Islands
How to Book Your Windward Islands Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. 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 Islands
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental 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 Islands
Tahiti
Papeete
Punaauia
Taiarapu-Est
Taiarapu-Ouest
Afaahiti
Papara
Pa'ofa'i
Frequently Asked Questions About Windward Islands Winter Rentals
1. What are the top Winter Rentals in Windward Islands?
There are a lot of options in Windward Islands. If you plan on staying in the Windward Islands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Windward Islands:
- Suite F2 Arue Tahiti seaside free access swimming pool spa gym
- TAHITI - Love Nest
- Charming 1-bedroom apartment in lovely Papeete entrance.
- TAHITI - Mango Lodge Matie
- TAHITI - Fare Matavai Hoe
- Manava Tahara'a home stay
- Luxury Eden & SPA: Private Jacuzzi Moorea View Pool Fiber Wi-Fi
- TAHITI - Taharuu Bungalow Surf Piti
- Kavai City - brand new 2 bedr 2bth A/C - Wi-Fi - parking
- SUITE by Chalet de Tahiti
2. How many Winter Rentals are available in Windward Islands?
Currently, the total number of properties listed by RBO in 2026 is over 206 in the Windward Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Windward Islands.
More Rentals You May Like Near Windward Islands
322.92 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Hot Tub
- Spa
CA $285/Night
For 7 Nights CA $1,998
969 ft²
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
Apartment
- Pool
- Ocean View
- Balcony/Terrace
CA $512/Night
For 7 Nights CA $3,581
269 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Oceanfront
- Hot Tub
- Ocean View
CA $200/Night
For 7 Nights CA $1,403
377 ft²
2 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Ski Chalet
- Balcony/Terrace
- Kitchen
- Parking
CA $145/Night
For 7 Nights CA $1,016
323 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $124/Night
For 7 Nights CA $871
CA $764/Night
For 7 Nights CA $5,347
377 ft²
2 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Ski Chalet
- Balcony/Terrace
- Kitchen
- Parking
CA $146/Night
For 7 Nights CA $1,023
1184 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- Kitchen
CA $326/Night
For 7 Nights CA $2,280
323 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Ski Chalet
- Pool
- Balcony/Terrace
- Kitchen
CA $227/Night
For 7 Nights CA $1,591
4306 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
CA $1,092/Night
For 7 Nights CA $7,648
1346 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Ski Chalet
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $490/Night
For 7 Nights CA $3,428
861 ft²
10 Guests
1 Bedroom
1 Bathroom
Family Friendly
Ski Chalet
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $457/Night
For 7 Nights CA $3,195
