Castle In Hawaii - Vacation Rentals in Windward Coast

Paradise Bay Resort From US $423
         

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8.2 (478 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious Waterfront with Gorgeous View & Pool From US $937
         

10.0 (9 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Beachfront spectacular Kailua beach From US $2,050
         

10.0 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Windward Coast

Over 594+ Luxury Places to Stay in or Near Windward Coast
Luxury beachfront villa on a world class beach in Kailua, HI From US $4,254
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787 From US $4,216
         

Top-Rated Vacation Rentals with a Pool in Windward Coast

Over 178+ Top-Rated Vacation Rentals with a Pool in or Near Windward Coast
Amazing Kailua Beach Front Licensed Rental #1990/NUC-1802 From US $2,823
         

10.0 (228 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Kailua Oceanfront Villa with Heated Pool & Spa From US $710
         

10.0 (111 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Windward Coast

Over 49+ Pet-Friendly Vacation Rentals in or Near Windward Coast
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen From US $255
         

10.0 (5 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Beachfront spectacular Kailua beach From US $1,224
         

9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Coconut Grove Cottage, Walk to Beach and Downtown From US $300
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Coconut Grove, Kailua Vacation Home From US $453
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Coconut Grove Kailua Vacation Home From US $307
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Tradewind Bungalow, in Kailua on Oahu From US $186
         

9.8 (145 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Windward Coast

Over 135+ Large Vacation Homes & Villas in or Near Windward Coast
Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach! From US $907
         

Waimanalo Beach Cottages From US $507
         

8.8 (31 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
Executive Balinese Vacation Home in Hawaii Kai From US $1,043
         

Zen Home with AC, Pool, Near Kailua Beach From US $1,068
         

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

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 $270
         

Available and legal for stays less than 30 days. From US $344
         

10.0 (112 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 111+ Windward Coast Vacation Rentals and Airbnb Places to Stay Under $200
Oahu Camper Adventures From US $125
         

9.1 (65 Reviews)
Boat Rental
  • Parking
  • View
  • Security/Safety
Cozy Kaaawa Studio with Mountain Views - 30 Day Min From US $123
         

Footsteps to Hawaii's Best Beach From US $141
         

10.0 (55 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Footsteps to Hawaii's Best Beach From US $134
         

10.0 (45 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Windward Coast

Over 254+ Instantly Bookable Vacation Homes in or Near Windward Coast
MONTHLY DISCOUNT! 3Bed/2Ba House - 250 Steps to the Beach! From US $450
         

Hale Pohaku, Waimanalo - Lic.#1990/NUC-1689 From US $1,433
         

About Windward Coast Vacation Rentals

With more than 27 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 1407.8 ft² on average, with prices averaging $1,370 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 25
Others 1
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 27 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.