Family Friendly Villas | For Families - Vacation Rentals in Windward

Property Image From $4,432
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $1,582
         

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10.0 (1 Review)
Villa
  • 3229 ft² Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $943
         

Property Image From $727
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From $871
         

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8.3 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $560
         

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

Luxury Places to Stay in Windward

Over 2433+ Luxury Places to Stay in or Near Windward
Property Image From $28,111
         

Top-Rated Vacation Rentals with a Pool in Windward

Over 2268+ Top-Rated Vacation Rentals with a Pool in or Near Windward
Property Image From $1,726
         

10.0 (35 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $4,418
         

Property Image From $395
         

Property Image From $1,021
         

10.0 (23 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $1,667
         

10.0 (20 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $642
         

Pet-Friendly Vacation Rentals in Windward

Over 283+ Pet-Friendly Vacation Rentals in or Near Windward
Property Image From $1,302
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $5,628
         

New
Villa
  • 1614 ft² Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $191
         

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9.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $296
         

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9.3 (9 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • View
See More Pet-Friendly Vacation Rentals in Windward on PetFriendly.io

Large Vacation Homes & Villas in Windward

Over 2242+ Large Vacation Homes & Villas in or Near Windward
Property Image From $529
         

8.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $912
         

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10.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $9,473
         

New
Villa
  • 3767 ft² Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $596
         

9.5 (9 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View
Property Image From $587
         

9.4 (3 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From $1,180
         

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9.3 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Windward

Over 54+ Wheelchair Accessible Vacation Homes in or Near Windward
Property Image From $13,018
         

Property Image From $4,525
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $1,515
         

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9.8 (77 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $3,208
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $3,084
         

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9.5 (24 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Windward Varoom and Airbnb Places to Stay Under $200

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

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $168
         

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9.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Property Image From $117
         

New
Villa
  • 2690 ft² Villa
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Windward

Over 804+ Instantly Bookable Vacation Homes in or Near Windward
Property Image From $1,403
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • TV
  • View
Property Image From $1,989
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From $1,437
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • TV
  • View
Property Image From $665
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From $640
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From $466
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • TV
  • View
Property Image From $530
         

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

About Windward Vacation Rentals

With more than 2442 Windward vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Familyfriendlyvillas 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 Familyfriendlyvillas 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 907.17 ft² on average, with prices averaging $3,695 a night.

Familyfriendlyvillas 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 2254
Vacation Homes 115
Holiday Apartments 46
Hotels with Suites 19
Cabin Rentals 3
B&B 1
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Windward

Pro Tip: Familyfriendlyvillas makes it easy to compare the best listings on Familyfriendlyvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Familyfriendlyvillas 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