It's practically impossible to find a Kailua vacation home without a good view. Whether you have a balcony overlooking the azure waters of the Pacific Ocean or a front door opening onto a luxurious pool, you'll be able to easily enjoy Hawaii's gorgeous landscape and warm temperatures. When you're tired of all the beach time, Kailua has plenty to keep you busy: markets, restaurants, bars, and adorable boutique shops abound.
Top 15 Recommended vacation rentals in Kailua
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Popular Rental Amenities in Kailua
Nearly half of the vacation homes offer a pool, which makes Kailua an excellent vacation destination for vacationers looking to spend vacation poolside. Additionally, more apartment rental have a pool than cottage. Most of the apartment rental with pools in Kailua accommodate 3 guests and have an average cost of $1,975 per night. If you would ideally like to be close to the water, many of the vacation homes providing a pool are located within 2 kilometres of the waterfront.
Price and Availability Index in Kailua
Vacation Rental Price Information in Kailua
The graph shows average prices of rentals in Kailua for the next twelve months. The most expensive week to book a vacation rental in Kailua is in September (9/5 – 9/12). The cheapest week to book a vacation rental is in November (11/22 – 11/29).
Rental availability information in Kailua
Check how busy Kailua is with our availability graph. The week with the highest booking rate is in October (10/10 – 10/17). Only 23% of the rentals are still available. The week with the most available rentals is in November (11/22 – 11/29), with 80% of the vacation rentals available.
Sightseeing in Kailua
Kailua Beach Park
Clear water and pristine white sand make this beach park the perfect place for water sports and aquatic activities. Rent some snorkel gear and look for tropical fish, or grab a kayak and hit the calm waves.
Lanikai Beach
Lanikai means "heavenly sea," and there's no better description for a beach such as this one. Although it's less than a mile long, Lanikai Beach is dubbed one of the best beaches in the world. You'll understand why when you see it.
Lanikai Pillboxes
The Lanikai Pillbox Hike is a moderately difficult but insanely scenic hiking trail with sweeping vistas overlooking the ocean and Kailua's unique landscape. You'll need about 90 minutes to complete this trail, and you'll definitely want to bring your camera.
Kalama Beach Park
Also known as Boettcher Estate, the Kalama Beach Park has the same white sands and turquoise waters of Kailua Beach. This beach is especially popular among windsurfers, bodyboarders, and kitesurfers. If that's not your thing, feel free to relax on the beach with a good book.
Olomana Three Peaks Trail
Olomana Three Peaks Trail is a challenging, rugged hike, but the rewards are well worth it. Thrill seekers, take note: the narrow path sometimes plunges to dramatic depths up to 1,600 feet on each side. Take in the views, but be careful with your footing.
Information about vacation rentals in Kailua
| 🏡 Vacation rentals available | 261 rentals |
|---|---|
| 🌙 Nightly prices starting at | $180 |
| ⭐ Popular amenities | Pool, Internet and Air conditioning |
| 🐾 Pet friendly homes | 19 homes |
| 🏊 Vacation rentals with pools | 104 homes |
Frequently Asked Questions
What is the typical availability of vacation rentals in Kailua?
November has the highest availability of House rental in Kailua, so you can expect a lot of vacation rentals available, even for last-minute bookings.
What are the most popular vacation home amenities in Kailua?
Many travellers are searching for Pool, Internet, and Air conditioning when booking a vacation home in Kailua.
Are there pet-friendly vacation rentals in Kailua?
Yes, there are 19 pet-friendly vacation rentals in Kailua, with an average nightly price of $1,079.
What's the best month to visit Kailua?
When booking a vacation rental in Kailua, remember that the rainiest months are usually May and July, with November often being the sunniest.
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