What are the top rated Winter Rentals in Kailua?

There are a lot of options in Kailua. If you plan on staying in the Kailua area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Kailua: <a href="/property/steps-to-beach-heated-pool-ac-gated-community-minimum-stay-7-nights-contact-host/HA-321170920" class="class="static-page-link"">Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST</a> <a href="/property/beachside-kailua-ac-3min-to-beach-dates-avail-min-stay-7-nights-contact-host/HA-321240222" class="class="static-page-link"">Beachside Kailua AC 3min to beach - DATES AVAIL! Min Stay 7 Nights-CONTACT HOST</a> <a href="/property/kailua-steps-to-the-beach/HA-321192693" class="class="static-page-link"">KAILUA-STEPS TO THE BEACH</a> <a href="/property/steps-to-beach-heated-pool-ac-minimum-stay-7-nights-contact-host/HA-32110797" class="class="static-page-link"">Steps to Beach- Heated Pool- AC-Minimum Stay 7 Nights-CONTACT HOST</a> <a href="/property/just-40-steps-to-the-most-beautiful-white-sand-beach-in-the-world/HA-121191624" class="class="static-page-link"">Just 40 Steps to the Most Beautiful White Sand Beach in the World</a> <a href="/property/happy-house-on-exquisite-kailua-beachside-property/HA-321246713" class="class="static-page-link"">Happy House on Exquisite Kailua Beachside Property!</a> <a href="/property/gorgeous-lankai-villa-with-access-to-secluded-white-sand-beach/HA-321712230" class="class="static-page-link"">Gorgeous Lankai Villa with Access to Secluded White Sand Beach</a> <a href="/property/kailua-beach-lofty-bungalow-a-premier-luxury-beachside-bungalow/HA-3212843338" class="class="static-page-link"">Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow</a> <a href="/property/large-beautiful-updated-home-w-pool-ac-mins-from-beach-in-kailua/HA-3212466450" class="class="static-page-link"">Large, beautiful, updated home w/pool, AC,mins from beach in Kailua!</a> <a href="/property/beautiful-beachside-bungalow/HA-321783263" class="class="static-page-link"">Beautiful Beachside Bungalow</a>

How much does it cost to rent a place to stay near Kailua in the wintertime?

The average cost for winter rentals in Kailua is $1,152 per night. Bigislandhawaiirental has a wide list of great winter places to stay near Kailua that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Do you have any winter rentals in Kailua that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Kailua to find what works for you.

Are there winter accommodations in Kailua that have indoor swimming pools?

As of 2026, the data from Bigislandhawaiirental shows that there are over 184 private swimming pools or indoor pools accommodations near Kailua along with other great amenities.

Winter Rentals in Kailua:【 GREAT PRICES 】

Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!

From US $317

10.0 (135 Reviews)

Cottage

Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!

Air Conditioner
Parking
TV

Kailua Winter Rentals & Holiday Homes

Discover winter rentals Kailua - We found 184 exact matches

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