Windward All-Inclusive Resorts, Hotels & Rentals

Plan Your Next Vacation to Windward to Relax, Recharge & Re-imagine

Property Image From US $4,432
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $943
         

Property Image From US $976
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From US $715
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From US $765
         

10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From US $529
         

8.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Windward

Over 2549+ Luxury Places to Stay in or Near Windward

Top-Rated Vacation Rentals with a Pool in Windward

Over 2314+ Top-Rated Vacation Rentals with a Pool in or Near Windward
Property Image From US $1,397
         

10.0 (35 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $3,400
         

10.0 (20 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $638
         

Pet-Friendly Vacation Rentals in Windward

Over 282+ Pet-Friendly Vacation Rentals in or Near Windward
Property Image From US $1,302
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $750
         

10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Property Image From US $390
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Child Friendly
Property Image From US $862
         

9.4 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Windward on PetFriendly.io

Large Vacation Homes & Villas in Windward

Over 2237+ Large Vacation Homes & Villas in or Near Windward
Property Image From US $800
         

Property Image From US $871
         

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8.3 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From US $1,692
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • TV
  • View
Property Image From US $2,002
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From US $1,501
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • TV
  • View
Property Image From US $909
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV

Wheelchair Accessible Vacation Homes in Windward

Over 59+ Wheelchair Accessible Vacation Homes in or Near Windward
Property Image From US $2,078
         

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9.8 (77 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Windward Varoom and Airbnb Places to Stay Under $200

Over 3+ Windward Varoom and Airbnb Places to Stay Under $200
Property Image From US $194
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $191
         

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9.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $168
         

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9.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View

Instantly Bookable Vacation Homes in Windward

Over 792+ Instantly Bookable Vacation Homes in or Near Windward
Property Image From US $518
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • TV
  • View
Property Image From US $625
         

9.8 (7 Reviews)
Villa
  • Air Conditioner
  • TV
  • View

About Windward Vacation Rentals

With more than 2558 Windward vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Allinclusivebeachresorts and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windward.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Allinclusivebeachresorts Windward, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windward. Places to stay near Windward are 1038.7 ft² on average, with prices averaging $4,101 a night.

Allinclusivebeachresorts makes it easy and safe to find and compare vacation rentals in Windward with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windward

Type Count
Villas 2203
Vacation Homes 282
Holiday Apartments 47
Hotels with Suites 17
Cabin Rentals 3
B&B 2
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Windward

Pro Tip: Allinclusivebeachresorts makes it easy to compare the best listings on Allinclusivebeachresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Allinclusivebeachresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windward.

Weather in Windward

View the weather forecast for Windward before booking your Windward Vacation Rentals to confirm your best time to go.

December - February
High 86°F       Low 73°F
March - May
High 87°F       Low 74°F
June - August
High 89°F       Low 77°F
September - November
High 90°F       Low 75°F