Windward Islands Summer Rental

10.0
Exceptional
(37 Reviews)
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
10.0
Exceptional
(12 Reviews)
1399.31 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Free Cancellation Villa
  • Oceanfront
  • Pool
  • Ocean View
CA $399/Night For 7 Nights CA $2,794
10.0
Exceptional
(6 Reviews)
1 Bedroom 1 Bathroom
Family Friendly House
  • Pool
  • Balcony/Terrace
  • View
CA $228/Night For 7 Nights CA $1,594
10.0
Exceptional
(30 Reviews)
646 ft² 5 Guests 2 Bedrooms 1 Bathroom
Ocean View House
  • Private Pool
  • Oceanfront
  • Pool
CA $511/Night For 7 Nights CA $3,580
10.0
Exceptional
(9 Reviews)
861.11 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Free Cancellation Villa
  • Pool
  • Balcony/Terrace
  • View
CA $247/Night For 7 Nights CA $1,728
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 $1,343
10.0
Exceptional
(7 Reviews)
861.11 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View Apartment
  • Oceanfront
  • Pool
  • Ocean View
CA $523/Night For 7 Nights CA $3,663
10.0
Exceptional
(22 Reviews)
484 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Pool
  • Ocean View
CA $146/Night For 7 Nights CA $1,024
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 $1,650
10.0
Exceptional
(21 Reviews)
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
10.0
Exceptional
(4 Reviews)
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
10.0
Exceptional
(19 Reviews)
6 Guests 3 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
CA $724/Night For 7 Nights CA $5,072

Why Choose Rent By Owner for your Windward Islands Summer Rental?

What makes our Summer Rental 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 Luxury Rentals

2. How many Summer Rentals are available in Windward Islands?

Currently, the total number of properties listed by RBO in 2026 is over 1063 in the Windward Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Summer Rentals in Windward Islands. 

More Rentals You May Like Near Windward Islands

10.0
Exceptional
(3 Reviews)
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
10.0
Exceptional
(15 Reviews)
1722 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View Condo
  • Oceanfront
  • Pool
  • Ocean View
CA $586/Night For 7 Nights CA $4,102
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 $1,349
10.0
Exceptional
(14 Reviews)
2153 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
CA $674/Night For 7 Nights CA $4,716
10.0
Exceptional
(14 Reviews)
861 ft² 4 Guests 2 Bedrooms 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Pool
  • Ocean View
CA $423/Night For 7 Nights CA $2,961
10.0
Exceptional
(12 Reviews)
4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
CA $432/Night For 7 Nights CA $3,021
10.0
Exceptional
(12 Reviews)
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
10.0
Exceptional
(11 Reviews)
3229 ft² 11 Guests 4 Bedrooms 2 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
CA $1,383/Night For 7 Nights CA $9,680
10.0
Exceptional
(11 Reviews)
2153 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Pool
  • Ocean View
CA $595/Night For 7 Nights CA $4,168
10.0
Exceptional
(11 Reviews)
969 ft² 4 Guests 2 Bedrooms 1 Bathroom
Ocean View Condo
  • Oceanfront
  • Pool
  • Ocean View
CA $377/Night For 7 Nights CA $2,639
10.0
Exceptional
(10 Reviews)
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
10.0
Exceptional
(7 Reviews)
8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Kitchen
  • Parking
  • Air Conditioner
CA $257/Night For 7 Nights CA $1,797