Chicago\92s Best Vacation Rentals - Vacation Rentals in Kawailoa Beach
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- TV
Apartment
- Air Conditioner
- Parking
- Pool
Condo
- Air Conditioner
- Parking
- Pool
Condo
- Air Conditioner
- Parking
- Pool
Condo
- Air Conditioner
- Parking
- Pool
Condo
- Air Conditioner
- Parking
- Pool
Condo
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Pool
- TV
House
- Air Conditioner
- Parking
- Pool
Condo
- Air Conditioner
- TV
- Wheelchair Accessible
★ Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals 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 Kawailoa Beach.
Weather in Kawailoa Beach
View the weather forecast for Kawailoa Beach before booking your Kawailoa Beach 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
Kawailoa Beach Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Kawailoa Beach?
There are a lot of options in Kawailoa Beach. If you plan on staying in the Kawailoa Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kawailoa Beach:
- Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park
- Poipu Bay Getaway - Poipu House - Saltwater pool, hot tub, AC!, Walk to Beach and Hyatt!
- Delightful Historic Cottage Steps from Poipu Beach A/C. No hurricane damage!
- Poipu Beach Plantation Style Cottage
- New Custom Hawaiian Cottage - Poipu Beach- Koloa, Hi
- Ocean View 3BR at Makahuena | Lanai, Pool, AC
- LUXURY VILLA, 3 Private Suites, Pool/Spa, Gym, Central A/C, Beach
- Nihi Kai #602 - Save 20% in Sept/Oct 2026!
- Fabulous Location near Shipwreck Beach and Grand Hyatt Resort
- MOST STUNNING Oceanfront Views, A/c, Washer/Dryer, Kitchen, Elevator, Beach 0.5m
How many vacation rentals are available in Kawailoa Beach?
Currently, the total number of properties listed in 2026 is over 1525 in the Kawailoa Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kawailoa Beach.