Windward Islands Villa

10.0
Exceptional
(37 Reviews)
2583 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Hot Tub
CA $2,097/Night For 7 Nights CA $14,677
10.0
Exceptional
(12 Reviews)
1399.31 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Free Cancellation Villa
  • Oceanfront
  • Pool
  • Ocean View
CA $400/Night For 7 Nights CA $2,803
New
1 Bedroom 1 Bathroom
Couples Retreat Villa
  • Parking
  • Internet
  • Child Friendly
CA $771/Night For 7 Nights CA $5,397
10.0
Exceptional
(19 Reviews)
6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
CA $727/Night For 7 Nights CA $5,088
10.0
Exceptional
(9 Reviews)
861.11 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Free Cancellation Villa
  • Pool
  • Balcony/Terrace
  • View
CA $248/Night For 7 Nights CA $1,733
10.0
Exceptional
(14 Reviews)
2153 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
CA $676/Night For 7 Nights CA $4,731
10.0
Exceptional
(7 Reviews)
1291.67 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Free Cancellation Villa
  • Balcony/Terrace
  • View
  • Parking
CA $179/Night For 7 Nights CA $1,250
10.0
Exceptional
(11 Reviews)
3229 ft² 11 Guests 4 Bedrooms 2 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
CA $1,387/Night For 7 Nights CA $9,711
10.0
Exceptional
(4 Reviews)
430.56 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
CA $361/Night For 7 Nights CA $2,528
10.0
Exceptional
(7 Reviews)
269 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Villa
  • Oceanfront
  • Hot Tub
  • Ocean View
CA $201/Night For 7 Nights CA $1,408
10.0
Exceptional
(3 Reviews)
4359.38 ft² 8 Guests 4 Bedrooms 4 Bathrooms
Ocean View Villa
  • Oceanfront
  • Hot Tub
  • Spa
CA $887/Night For 7 Nights CA $6,210
10.0
Exceptional
(5 Reviews)
10 Guests 5 Bedrooms 3 Bathrooms
Group Friendly Villa
  • Pool
  • Child Friendly
  • Bedding/Linens
CA $1,671/Night For 7 Nights CA $11,698

Why Choose Rent By Owner for your Windward Islands Villa?

What makes our Villa 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.

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

Frequently Asked Questions About Windward Islands Rental Villas

1. What are the top Villas 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 Villas in Windward Islands:

2. How many Villas are available in Windward Islands?

Currently, the total number of properties listed by RBO in 2026 is over 165 in the Windward Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Windward Islands. 

More Rentals You May Like Near Windward Islands

10.0
Exceptional
(3 Reviews)
4 Guests 2 Bedrooms 2 Bathrooms
Free Cancellation Villa
  • Private Beach
  • Oceanfront
  • Ocean View
CA $314/Night For 7 Nights CA $2,199
10.0
Exceptional
(5 Reviews)
1938 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Villa
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
CA $346/Night For 7 Nights CA $2,423
10.0
Exceptional
(2 Reviews)
4306 ft² 8 Guests 4 Bedrooms 4 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Hot Tub
CA $1,096/Night For 7 Nights CA $7,672
10.0
Exceptional
(2 Reviews)
1399 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Pool
  • Balcony/Terrace
  • Pet Friendly
CA $540/Night For 7 Nights CA $3,779
10.0
Exceptional
(2 Reviews)
6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Private Pool
  • Pool
  • Balcony/Terrace
CA $498/Night For 7 Nights CA $3,485
10.0
Exceptional
(1 Review)
1 ft² 8 Guests 1 Bedroom 1 Bathroom
Family Friendly Villa
  • Parking
  • Air Conditioner
  • Internet
CA $839/Night For 7 Nights CA $5,870
10.0
Exceptional
(1 Review)
1615 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Pool
CA $834/Night For 7 Nights CA $5,835
10.0
Exceptional
(1 Review)
10 Guests 4 Bedrooms 4 Bathrooms
Group Friendly Villa
  • Hot Tub
  • Air Conditioner
  • Internet
CA $752/Night For 7 Nights CA $5,267
9.8
Exceptional
(7 Reviews)
4306 ft² 8 Guests 4 Bedrooms 4 Bathrooms
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Hot Tub
CA $1,123/Night For 7 Nights CA $7,858
9.8
Exceptional
(7 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Villa
  • Private Pool
  • Pool
  • Balcony/Terrace
CA $362/Night For 7 Nights CA $2,536
9.6
Exceptional
(14 Reviews)
6 Guests 3 Bedrooms 1 Bathroom
Family Friendly Villa
  • Private Pool
  • Pool
  • Balcony/Terrace
CA $1,060/Night For 7 Nights CA $7,423
9.6
Exceptional
(11 Reviews)
8 Guests 4 Bedrooms 3 Bathrooms
Pet Friendly Villa
  • Pet Friendly
  • Air Conditioner
  • Internet
CA $1,051/Night For 7 Nights CA $7,360