Top Vacation rentals in Windward Islands

Find the Top Vacation rentals in Windward Islands – 20+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-20 out of 20 vacation rentals
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Homestay
2 adults
1 bedroom
2 beds
From   US$ 140 /nightSelect
  • On-site wellness spa with hot tub
  • Family-friendly outdoor play equipment
  • Complimentary airport shuttle service
6 adults
1 bedroom
3 beds
From   US$ 176 /nightSelect
  • Private beach access with sun loungers
  • Fully equipped kitchen for convenient meals
  • Canoeing and fishing available on-site
  • Outdoor pool
  • Picnic area
  • Car rental
From   US$ 116 /nightSelect
  • Outdoor swimming pool with sun loungers
  • Family rooms with picnic area available
  • Fresh pastries and fruits served daily
Apartment
  • Rooftop Pool
  • Free Parking
  • Fully Equipped Kitchen
From   US$ 96 /nightSelect
  • Rooftop pool with city views
  • Private entrance and soundproofing
  • On-site coffee shop available
Holiday home
  • Private beach
  • Outdoor pool
  • Family rooms
From   US$ 215 /nightSelect
  • Beachfront private areas for relaxation
  • Outdoor pool with stunning mountain views
  • Canoeing adventures right at your doorstep
Holiday home
  • Private Beach
  • Outdoor Pools
  • Canoeing
From   US$ 202 /nightSelect
  • Private beach area for exclusive access
  • Scenic outdoor swimming pool options
  • Canoeing available for outdoor fun
Holiday home
  • Private Beach
  • Outdoor Dining
  • Water Sports
From   US$ 68 /nightSelect
  • Private beach access with mountain views
  • Full kitchen and outdoor dining area
  • On-site activities like fishing and diving
  • Private Beach
  • Outdoor Dining
  • Barbecue Facilities
From   US$ 808 /nightSelect
  • Beachfront property with private access
  • Fully equipped kitchen for convenience
  • On-site canoeing and hiking activities
  • Private Entrance
  • Outdoor Dining
  • Open-Air Bath
From   US$ 190 /nightSelect
  • Beachfront property with stunning views
  • Private garden with outdoor dining area
  • Year-round pool with mountain views
  • Private terrace
  • Free parking
  • Air conditioning
From   US$ 149 /nightSelect
  • Private entrance for added privacy
  • City views from private terrace
  • 24-hour front desk service
  • Infinity Pool
  • Picnic Area
  • Beach Access
From   US$ 495 /nightSelect
  • Spectacular infinity pool with sea views
  • Air-conditioned units with kitchen options
  • Breakfast with fresh pastries and fruits
  • Beach Access
  • Sea Views
  • Private Terrace
From   US$ 219 /nightSelect
  • Beachfront access to Lafayette Beach
  • Fully equipped kitchen for cooking
  • Terrace with stunning sea views
  • Outdoor Terrace
  • Electric Vehicle Charging
  • Flat-Screen TV
From   US$ 208 /nightSelect
  • Breathtaking ocean and Moorea views
  • Private outdoor dining area
  • Spacious outdoor swimming pool
  • Private Pool
  • Sea Views
  • Free Parking
From   US$ 243 /nightSelect
  • Private pool with gorgeous sea views
  • Air-conditioned apartment with patio
  • Free private parking available onsite
  • Private Beach
  • Open-Air Bath
  • Picnic Area
From   US$ 553 /nightSelect
  • Private beach with garden views
  • On-site open-air massage services
  • Activities for snorkeling and canoeing
Holiday home
  • Private Pool
  • Air Conditioning
  • Outdoor Dining
From   US$ 146 /nightSelect
  • Private pool for exclusive enjoyment
  • Air-conditioned holiday home with patio
  • Outdoor dining area with garden views
  • Private beach
  • Outdoor play
  • Picnic area
From   US$ 239 /nightSelect
  • Private beach access for relaxation
  • Children's outdoor play equipment available
  • Fully equipped kitchen for convenience
  • Rooftop Pool
  • Fully Equipped Kitchen
  • Air Conditioning
From   US$ 217 /nightSelect
  • Rooftop swimming pool with scenic views
  • Fully equipped kitchen for home cooking
  • Air-conditioned spacious apartment layout
Apartment
  • Outdoor pool
  • Canoeing
  • Garden area
From   US$ 155 /nightSelect
  • Outdoor swimming pool with mountain views
  • Canoeing activities available nearby
  • Spacious balcony with sea views
  • Hot Tub
  • Fitness Centre
  • Tennis Court
From   US$ 235 /nightSelect
  • Private hot tub with sea views
  • Fully equipped kitchen for convenience
  • Tennis court for recreational activities