Windward Islands Resorts

8.5
Fabulous
(672 Reviews)
363.1 ft² 49 Guests 15 Bathrooms
Free Cancellation Resort
  • Oceanfront
  • Spa
  • Fireplace/Heating
CA $685/Night For 7 Nights CA $4,794
9.0
Exceptional
(1002 Reviews)
1 Bathroom
Family Friendly Resort
  • Spa
  • Pool
  • Balcony/Terrace
CA $778/Night For 7 Nights CA $5,445
8.5
Fabulous
(10 Reviews)
778.23 ft² 30 Guests 10 Bathrooms
Free Cancellation Resort
  • Private Beach
  • Oceanfront
  • Pool
CA $388/Night For 7 Nights CA $2,718
9.0
Exceptional
(25 Reviews)
1 Bathroom
Family Friendly Resort
  • Pool
  • Balcony/Terrace
  • Breakfast
CA $522/Night For 7 Nights CA $3,654
8.0
Excellent
(784 Reviews)
748.09 ft² 56 Guests 19 Bathrooms
Free Cancellation Resort
  • Oceanfront
  • Hot Tub
  • Spa
CA $560/Night For 7 Nights CA $3,918
7.8
Very Good
(441 Reviews)
1 Bathroom
Ocean View Resort
  • Private Pool
  • Pool
  • Ocean View
CA $294/Night For 7 Nights CA $2,059
8.2
Excellent
(1237 Reviews)
607.08 ft² 31 Guests 1 Bathroom
Free Cancellation Resort
  • Oceanfront
  • Spa
  • Pool
CA $710/Night For 7 Nights CA $4,970
7.2
Very Good
(1168 Reviews)
631.48 ft² 13 Guests 3 Bathrooms
Free Cancellation Resort
  • Hot Tub
  • Spa
  • Pool
CA $301/Night For 7 Nights CA $2,107
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
10.0
Exceptional
(6 Reviews)
1 Bedroom 1 Bathroom
Family Friendly House
  • Pool
  • Balcony/Terrace
  • View
CA $228/Night For 7 Nights CA $1,599
10.0
Exceptional
(30 Reviews)
646 ft² 5 Guests 2 Bedrooms 1 Bathroom
Ocean View House
  • Private Pool
  • Oceanfront
  • Pool
CA $513/Night For 7 Nights CA $3,591

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Why Choose Rent By Owner for your Windward Islands Resorts?

What makes our Resorts 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 Resorts

2. How many Resorts are available in Windward Islands?

Currently, the total number of properties listed by RBO in 2026 is over 8 in the Windward Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Windward Islands. 

More Rentals You May Like Near Windward Islands

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
(23 Reviews)
646 ft² 4 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
CA $192/Night For 7 Nights CA $1,348
10.0
Exceptional
(7 Reviews)
861.11 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Pool
  • Ocean View
CA $525/Night For 7 Nights CA $3,675
10.0
Exceptional
(22 Reviews)
484 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Pool
  • Ocean View
CA $147/Night For 7 Nights CA $1,030
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
(21 Reviews)
3983 ft² 10 Guests 4 Bedrooms 3 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Hot Tub
CA $1,456/Night For 7 Nights CA $10,191
10.0
Exceptional
(7 Reviews)
150.69 ft² 4 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Balcony/Terrace
  • View
  • Parking
CA $135/Night For 7 Nights CA $948
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
(4 Reviews)
430.56 ft² 4 Guests 1 Bedroom 1 Bathroom
Free Cancellation House
  • Pool
  • Balcony/Terrace
  • View
CA $236/Night For 7 Nights CA $1,655
10.0
Exceptional
(15 Reviews)
1722 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View Condo
  • Oceanfront
  • Pool
  • Ocean View
CA $588/Night For 7 Nights CA $4,115
10.0
Exceptional
(15 Reviews)
624 ft² 6 Guests 3 Bedrooms 1 Bathroom
Ocean View House
  • Private Pool
  • Oceanfront
  • Pool
CA $193/Night For 7 Nights CA $1,353
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

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