Airport Express Hotel - Vacation Rentals in Windward Coast

Paradise Bay Resort From US $271
         

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8.8 (1012 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Windward Coast

Over 596+ 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
         

Ocean Front Lanikai - Lic. Rental #1990/NUC-1757 From US $3,850
         

10.0 (132 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA From US $3,780
         

Amazing Kailua Beach Front Licensed Rental #1990/NUC-1802 From US $3,571
         

10.0 (227 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Windward Coast

Over 181+ Top-Rated Vacation Rentals with a Pool in or Near Windward Coast
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 47+ Pet-Friendly Vacation Rentals in or Near Windward Coast
Beachfront spectacular Kailua beach From US $1,224
         

9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen From US $227
         

10.0 (5 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Coconut Grove Cottage, Walk to Beach and Downtown From US $279
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Coconut Grove, Kailua Vacation Home From US $421
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Oceanfront 3-Bedroom Home in Kahaluu, Kaneohen30 days minimum rental. From US $311
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Tradewind Bungalow, in Kailua on Oahu From US $186
         

9.8 (144 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Keolu Hills Haven: Renovated 2/2 & Easy Parking From US $317
         

Large Vacation Homes & Villas in Windward Coast

Over 143+ Large Vacation Homes & Villas in or Near Windward Coast
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
Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach! From US $1,228
         

Panoramic Ocean & Mountain Views -we have FULL AVAILABILITY please message us.n From US $1,626
         

10.0 (2 Reviews)
Bed & Breakfast
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Executive Balinese Vacation Home in Hawaii Kai From US $1,043
         

Wheelchair Accessible Vacation Homes in Windward Coast

Over 14+ Wheelchair Accessible Vacation Homes in or Near Windward Coast
Paradise Bay Resort From US $1,657
         

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8.3 (502 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunny Kailua Home w/Covered Lanai 1 Mi to Beach! From US $263
         

Available and legal for stays less than 30 days. From US $342
         

10.0 (109 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
         

9.4 (63 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
*Affordable Island Getaway with private yard * From US $179
         

Instantly Bookable Vacation Homes in Windward Coast

Over 257+ 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 $1,393
         

About Windward Coast Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Airportexpresshotel 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 with prices averaging $271 a night.

Airportexpresshotel 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
Hotels with Suites 1

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

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

There are a lot of options in Windward Coast. If you plan on staying in the Windward Coast area, consider making a reservation for a few nights at one of these properties as these have been rated 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 1 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.