Discover winter rentals Kailua - We found 178 exact matches
About Kailua Winter Rental on Hawaii.Villas
Planning a winter vacation in Kailua? Discover 178 places to stay, ideal for family trips, group getaways, or wedding retreats.
At HawaiiVillas, explore a wide range of accommodations in Kailua, HI perfect for your winter escape. Our listings feature private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, all equipped with top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Winter accommodations in Kailua start at US $1,122, with popular options including cabins, bungalows, and privately owned rental homes. Planning a snowboarding adventure? We offer numerous snowboard-friendly ski resorts, chalets, and cabins available for short-term or extended stays, whether for a weekend getaway or a longer retreat.
HawaiiVillas provides great deals for travelers seeking rentals in Kailua. To secure your winter vacation home, visit HawaiiVillas, use our filter options to specify your travel dates, property type, and desired amenities. Choose from a comprehensive list of winter vacation rentals hassle-free. Explore our interactive map to discover all lodging options in and around Kailua and unlock exclusive deals.
Frequently Asked Questions About Kailua Winter Rentals
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:
- Amazing & Large Kailua Beachfront for up to 14 guests
- PRIVATE BEACHFRONT RENTAL
- Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
- Ocean Front Lanikai - Amazing Views!
- 'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
- Steps to Beach-Heated Pool-AirCon-Gated Community-Min Stay 7 Nights-CONTACT HOST
- Best Price and Location on Beautiful Kailua Beach!
- Kailua Oceanfront Villa with Heated Pool & Spa - SEPTEMBER now available!
- Charming Lanikai Cottage. Close to beach, A/C, parking.
- Beachside Kailua AC 3min to beach - DATES AVAIL! Min Stay 7 Nights-CONTACT HOST
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 $1,122 per night. Hawaii.Villas 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.
Are there any winter cottages/chalets in Kailua that allow pets?
Yes, here are the top cottage/chalet rentals in Kailua that allow you to bring your pet or dog:
- Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
- Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
- Palione Papalani by Avantstay New $1.5m Remodel Steps From Kailua Beach w/Private Pool & Hot Tub
- Kailua Oceanfront Villa with Heated Pool & Spa - SEPTEMBER now available!
See all pet-friendly vacation rentals in Kailua on Hawaii.Villas
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 2025, the data from Hawaii.Villas shows that there are over 178 private swimming pools or indoor pools accommodations near Kailua along with other great amenities.
Do any winter holiday rentals in Kailua have hot tubs?
About 178 holiday rentals in Kailua boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Kailua?
Yes, there are many luxury places to stay in Kailua for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Kailua with all the best amenities for your next trip.
