Castle In Hawaii - Vacation Rentals in Windward Coast

Spacious Waterfront with Gorgeous View & Pool From US $991
         

10.0 (9 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Paradise Bay Resort From US $423
         

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8.0 (458 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Beachfront spectacular Kailua beach From US $2,062
         

10.0 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Frangipani Tropical Beachside Retreat Kailua From US $668
         

Luxury Places to Stay in Windward Coast

Over 567+ Luxury Places to Stay in or Near Windward Coast
Luxury beachfront villa on a world class beach in Kailua, HI From US $4,520
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787 From US $4,111
         

Top-Rated Vacation Rentals with a Pool in Windward Coast

Over 162+ Top-Rated Vacation Rentals with a Pool in or Near Windward Coast
Kailua Oceanfront Villa with Heated Pool & Spa From US $710
         

10.0 (112 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hale Mokulua - Lanikai, Oahu/pools, spa, beach! From US $1,035
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Windward Coast

Over 51+ Pet-Friendly Vacation Rentals in or Near Windward Coast
Coconut Grove Cottage, Walk to Beach and Downtown From US $306
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Beachfront spectacular Kailua beach From US $1,224
         

9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Coconut Grove, Kailua Vacation Home From US $454
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Keolu Hills Haven: Renovated 2/2 & Easy Parking From US $286
         

The Cicak Shack - a perfect beach hideaway From US $169
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Windward Coast

Over 128+ Large Vacation Homes & Villas in or Near Windward Coast
Waimanalo Beach Cottages From US $507
         

8.4 (30 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxurious five-bedroom modern retreat From US $2,802
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Panoramic Ocean & Mountain Views -we have FULL AVAILABILITY please message us. From US $1,538
         

10.0 (2 Reviews)
Bed & Breakfast
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Zen Home with AC, Pool, Near Kailua Beach From US $1,120
         

9.8 (79 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA From US $3,298
         

Wheelchair Accessible Vacation Homes in Windward Coast

Over 13+ Wheelchair Accessible Vacation Homes in or Near Windward Coast
Sunny Kailua Home w/Covered Lanai 1 Mi to Beach! From US $254
         

Available and legal for stays less than 30 days. From US $387
         

10.0 (114 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Beachfront Cottage - Steps to beach, AC From US $1,367
         

Seascape Vista - Pool, AC From US $1,383
         

Windward Coast Vacation Rentals and Airbnb Places to Stay Under $200

Over 108+ Windward Coast Vacation Rentals and Airbnb Places to Stay Under $200
Kailani Loft, Kailua Coconut Grove 1-bedroom From US $193
         

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8.6 (52 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Cozy Kaaawa Studio with Mountain Views - 30 Day Min From US $132
         

Footsteps to Hawaii's Best Beach From US $153
         

10.0 (55 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Footsteps to Hawaii's Best Beach From US $145
         

10.0 (46 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Windward Coast

Over 236+ Instantly Bookable Vacation Homes in or Near Windward Coast
MONTHLY DISCOUNT! 3Bed/2Ba House - 250 Steps to the Beach! From US $521
         

About Windward Coast Vacation Rentals

With more than 25 Windward Coast vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Castleinhawaii 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 Coast.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Castleinhawaii Windward Coast, 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 Coast. Places to stay near Windward Coast are 1350.12 ft² on average, with prices averaging US $1,325 a night.

Castleinhawaii makes it easy and safe to find and compare vacation rentals in Windward Coast 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 Coast

Type Count
Villas 24
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Windward Coast

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

Weather in Windward Coast

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Windward Coast Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Windward Coast?
How many vacation rentals are available in Windward Coast?

Currently, the total number of properties listed in 2026 is over 25 in the Windward Coast area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windward Coast.