Discover Your Perfect Windward Islands Vacation Homes

Best Vacation Homes in Windward Islands

Villa
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like-icon10.0
Exceptional
(37 Reviews)
3 Bedrooms 2 Baths 6 Guests 2583 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
CA $1,863/Night 7 Nights - CA $13,043
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Villa
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like-icon10.0
Exceptional
(12 Reviews)
3 Bedrooms 2 Baths 6 Guests 1399.31 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
CA $405/Night 7 Nights - CA $2,834
House
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
1 Bedroom 1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $231/Night 7 Nights - CA $1,617
House
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like-icon10.0
Exceptional
(30 Reviews)
2 Bedrooms 1 Bath 5 Guests 646 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
CA $546/Night 7 Nights - CA $3,824
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Villa
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like-icon10.0
Exceptional
(9 Reviews)
2 Bedrooms 2 Baths 6 Guests 861.11 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $250/Night 7 Nights - CA $1,752
Apartment
Map-icon
like-icon10.0
Exceptional
(24 Reviews)
1 Bedroom 1 Bath 4 Guests 646 ft²
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
More amenities
CA $193/Night 7 Nights - CA $1,351
Apartment
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like-icon10.0
Exceptional
(22 Reviews)
1 Bedroom 1 Bath 2 Guests 484 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
CA $148/Night 7 Nights - CA $1,039
House
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like-icon10.0
Exceptional
(21 Reviews)
4 Bedrooms 3 Baths 10 Guests 3983 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
CA $1,636/Night 7 Nights - CA $11,449

Windward Islands Luxury Rentals

Villa
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5 Bedrooms 3 Baths 10 Guests 1614.59 ft²
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
More amenities
CA $2,708/Night 7 Nights - CA $18,959
New
Boat Rental
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2 Bedrooms 1 Bath 4 Guests
  • Child Friendly
    Child Friendly
  • Security/Safety
    Security/Safety
CA $2,391/Night 7 Nights - CA $16,739
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Villa
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6 Bedrooms 6 Baths 17 Guests 10763.91 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
CA $2,340/Night 7 Nights - CA $16,380
Villa
Map-icon
like-icon8.0
Excellent
(2 Reviews)
7 Bedrooms 12 Baths 28 Guests 388 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $2,298/Night 7 Nights - CA $16,086
Villa
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6 Bedrooms 6 Baths 17 Guests 2207 ft²
  • Air Conditioner
    Air Conditioner
  • Internet
    Internet
More amenities
CA $2,192/Night 7 Nights - CA $15,344
New
Villa
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5 Bedrooms 3 Baths 10 Guests
  • Ocean View
    Ocean View
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $1,812/Night 7 Nights - CA $12,683
Apartment
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1 Bedroom 1 Bath 4 Guests 431 ft²
  • Air Conditioner
    Air Conditioner
  • Internet
    Internet
More amenities
CA $1,801/Night 7 Nights - CA $12,611
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Villa
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3 Bedrooms 3 Baths 8 Guests 3498.27 ft²
  • View
    View
  • Air Conditioner
    Air Conditioner
More amenities
CA $1,671/Night 7 Nights - CA $11,698

Windward Islands Pet Friendly Vacation Rentals

Apartment
Map-icon
like-icon10.0
Exceptional
(13 Reviews)
2 Bedrooms 1 Bath 4 Guests 807 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
CA $307/Night 7 Nights - CA $2,150
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 3 Guests 527.43 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
CA $224/Night 7 Nights - CA $1,564
House
Map-icon
like-icon8.6
Fabulous
(163 Reviews)
1 Bedroom 1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $199/Night 7 Nights - CA $1,391
Villa
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 6 Guests 1399 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
CA $540/Night 7 Nights - CA $3,778
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House
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 2 Baths 7 Guests 1334.72 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
CA $497/Night 7 Nights - CA $3,481
Villa
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
CA $503/Night 7 Nights - CA $3,522
Ski Chalet
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 10 Guests 861 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Pet Friendly
    Pet Friendly
More amenities
CA $463/Night 7 Nights - CA $3,240
Villa
Map-icon
like-icon9.6
Exceptional
(11 Reviews)
4 Bedrooms 3 Baths 8 Guests
  • Pet Friendly
    Pet Friendly
  • Air Conditioner
    Air Conditioner
More amenities
CA $1,063/Night 7 Nights - CA $7,440

Windward Islands Large Vacation Homes

Villa
Map-icon
like-icon10.0
Exceptional
(20 Reviews)
3 Bedrooms 3 Baths 6 Guests
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
CA $739/Night 7 Nights - CA $5,172
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Villa
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
2 Bedrooms 2 Baths 4 Guests 1291.67 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
More amenities
CA $181/Night 7 Nights - CA $1,264
Villa
Map-icon
1 Bedroom 1 Bath
  • Parking
    Parking
  • Internet
    Internet
More amenities
CA $779/Night 7 Nights - CA $5,456
Villa
Map-icon
like-icon10.0
Exceptional
(14 Reviews)
4 Bedrooms 3 Baths 8 Guests 2153 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
CA $681/Night 7 Nights - CA $4,768
Villa
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
2 Bedrooms 2 Baths 4 Guests 430.56 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
CA $365/Night 7 Nights - CA $2,556
Villa
Map-icon
like-icon10.0
Exceptional
(12 Reviews)
4 Bedrooms 2 Baths 11 Guests 3229 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
CA $1,398/Night 7 Nights - CA $9,790
Villa
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
1 Bedroom 1 Bath 2 Guests 269 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
CA $197/Night 7 Nights - CA $1,380
Villa
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
5 Bedrooms 3 Baths 10 Guests
  • Pool
    Pool
  • Child Friendly
    Child Friendly
More amenities
CA $1,549/Night 7 Nights - CA $10,844

Why Choose Rent By Owner for your Windward Islands Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Windward Islands

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you experience the region’s natural beauty and pleasant weather, making it ideal for planning your stay in this stunning destination.

Peak Season Highlights

spring
June to October

This period marks the peak travel season when the region experiences warm weather and ideal conditions for outdoor activities. You'll enjoy longer daylight hours and vibrant local events, making it perfect for exploring the area.

Average Temperature Daytime: 28°C (82°F) - Nighttime: 22°C (72°F)
spring
December to April

During this season, the destination is popular among visitors seeking a dry and sunny climate. This is an excellent time to find favorable weather for beach days and water-based adventures in the region.

Average Temperature Daytime: 27°C (81°F) - Nighttime: 20°C (68°F)

Off-Season Highlights

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May and November

These shoulder months see fewer travelers, offering a more tranquil experience while still enjoying pleasant weather. It’s an ideal time for those looking to beat the crowds and find better rates on vacation rentals here.

Average Temperature Daytime: 26°C (79°F) - Nighttime: 19°C (66°F)
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May to June and October to November

The region tends to be quieter during these months, with occasional rain showers bringing lush greenery. This off-peak period allows you to explore at a relaxed pace and secure attractive deals on your accommodations.

Average Temperature Daytime: 27°C (81°F) - Nighttime: 21°C (70°F)

Weekly Weather Forecast for Windward Islands

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.

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

Outdoor Amenities

  • Enjoy a private outdoor swimming pool to cool off under the sun.
  • Relax in a shaded patio area perfect for outdoor dining or lounging.
  • Make the most of lush garden spaces that offer tranquil scenery and privacy.
  • Take advantage of stunning ocean views from your outdoor deck or balcony.
  • Utilize outdoor grilling facilities to prepare local cuisine while soaking in the scenery.
  • Benefit from direct access to nearby beaches or waterfronts for water activities.
  • Experience alfresco dining options that allow you to savor meals surrounded by nature.
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Family Activities

  • Snorkeling Safaris: Explore the vibrant marine life just off the coast, where clear waters reveal colorful coral reefs perfect for family-friendly snorkeling adventures.
  • Island Hopping Tours: Discover the diverse landscapes and hidden beaches of this destination by taking guided boat excursions to nearby islands.
  • Hiking Trails: Enjoy scenic hikes suitable for families, offering breathtaking views of lush valleys and coastal panoramas around the region.
  • Cultural Experiences: Engage with local traditions through performances and craft workshops that provide an enriching insight into the area's vibrant heritage.
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Adult Activities

  • Snorkeling and Diving Adventures: Explore the vibrant coral reefs teeming with marine life in the region, offering unforgettable underwater experiences just off the coast.
  • Hiking through Scenic Trails: Discover lush landscapes and panoramic vistas by trekking along well-maintained trails that showcase the area's natural beauty.
  • Relaxing on Pristine Beaches: Unwind on secluded sandy shores where clear turquoise waters invite tranquil beach days and water activities.
  • Cultural Tours and Local Cuisine: Immerse yourself in the local culture through authentic culinary experiences and guided tours of historical sites nearby.

Windward Islands Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Research local festivals and cultural events to enhance your experience and align your stay with vibrant happenings in the area.
  • Explore Nearby Beaches: Take advantage of the region’s stunning coastlines by visiting diverse beaches that showcase the natural beauty and tranquility here.
  • Choose a Strategic Location: Select a vacation rental situated near popular sights or transportation hubs to maximize your exploration time and convenience.
  • Engage with Local Cuisine: Savor authentic flavors by discovering nearby eateries or preparing fresh meals in your rental to immerse yourself in the regional culinary scene.

Transportation Options

  • Inter-Island Flights: You can conveniently travel between islands in the region using local airlines that offer regular scheduled flights, providing quick access to your preferred destination here.
  • Ferries and Boat Transfers: Water-based transportation such as ferries and boats serve as popular options for exploring the islands and enjoying scenic views of the surrounding waters.
  • Car Rentals: Renting a car on the islands allows you to explore remote beaches and hidden spots at your own pace, making it easier to access diverse vacation rentals in the area.
  • Public Transportation: Buses and shared taxis operate throughout the region, offering an economical way to navigate between towns and visit the most sought-after vacation rental locations here.

Local Customs Options

  • Respect for Local Tatau (Tattoo) Customs: You’ll find that traditional Polynesian tattooing holds deep cultural significance in the area, and participating respectfully when observing or engaging with tattoo artists is appreciated.
  • Embracing 'Aloha' Spirit and Hospitality: The warmth and friendliness of the local community emphasize genuine hospitality, so adopting a welcoming attitude enhances your experience here.
  • Adherence to Traditional Dance and Music Etiquette: When enjoying performances, it's important to observe proper etiquette, showing appreciation without disrupting the rhythm of the cultural displays.
  • Environmental Respect and Conservation Practices: Here, you'll notice a strong emphasis on protecting the pristine natural environment by following guidelines that prevent waste and preserve the region’s natural beauty.

Frequently Asked Questions About Windward Islands?

2. How many vacation rentals have private pools in Windward Islands?

There are 123 vacation rentals with private pools near Windward Islands. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Windward Islands are best for families?

If you are looking for a family-friendly vacation home in Windward Islands, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windward Islands:

4. How many Rentbyowner vacation rentals are available in Windward Islands?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 1478 in the Windward Islands area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windward Islands. 

5. What is the cancellation policy for vacation rentals in the Windward Islands, French Polynesia?

Cancellation policies vary by property owner, so it’s important to review the specific listing details. Some rentals offer flexible options, while others may have stricter conditions. Contact the host directly for clarification.

6. Are there any special requirements or house rules I should be aware of when booking a vacation rental here?

Each property has its own house rules listed on the property page. These can include restrictions on smoking, pets, or noise levels. Be sure to read these carefully and reach out to the owner if you have specific questions.

7. How do I confirm the availability of a vacation rental in this region?

Availability is displayed on each listing, but it’s recommended to contact the property owner directly to verify dates and receive confirmation before making your reservation.

8. What amenities are typically included in vacation rentals in this destination?

Amenities vary but often include essentials like Wi-Fi, air conditioning, kitchen facilities, and sometimes extras such as pool access or water sports equipment. Check the listing details for the exact amenities offered.

9. What should I know about the check-in and check-out process for these properties?

Check-in and check-out procedures are specified in each listing. Many hosts offer flexible options, but it’s best to confirm these details with the owner prior to your arrival to ensure a smooth stay.

Windward Islands Top Rated Vacation Rentals

Apartment
Map-icon
like-icon10.0
Exceptional
(42 Reviews)
1 Bedroom 1 Bath 4 Guests 753 ft²
  • Hot Tub
    Hot Tub
  • Spa
    Spa
More amenities
CA $245/Night 7 Nights - CA $1,719
Condo
Map-icon
like-icon10.0
Exceptional
(15 Reviews)
2 Bedrooms 2 Baths 4 Guests 1722 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
CA $595/Night 7 Nights - CA $4,164
House
Map-icon
like-icon10.0
Exceptional
(15 Reviews)
3 Bedrooms 1 Bath 6 Guests 624 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
CA $195/Night 7 Nights - CA $1,365
Apartment
Map-icon
like-icon10.0
Exceptional
(14 Reviews)
2 Bedrooms 1 Bath 4 Guests 861 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
CA $429/Night 7 Nights - CA $3,002
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
3 Bedrooms 2 Baths 6 Guests 2153 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
CA $604/Night 7 Nights - CA $4,226
Condo
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
2 Bedrooms 1 Bath 4 Guests 969 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
CA $389/Night 7 Nights - CA $2,723
Apartment
Map-icon
like-icon10.0
Exceptional
(10 Reviews)
3 Bedrooms 1 Bath 6 Guests 969 ft²
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
CA $536/Night 7 Nights - CA $3,753
Condo
Map-icon
like-icon10.0
Exceptional
(8 Reviews)
1 Bedroom 1 Bath 2 Guests 689 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
CA $226/Night 7 Nights - CA $1,583