Discover winter rentals Hawaii - We found 28660 exact matches
About Hawaii Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Hawaii, HI perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Hawaii. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Hawaii and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Hawaii Winter Rentals
What are the top rated Winter Rentals in Hawaii?
There are a lot of options in Hawaii. If you plan on staying in the Hawaii area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Hawaii:
- Hale Mauka Volcano Village Hawaii Volcanoes National Park
- Romantic & Breathtaking Oceanfront Kauai Condo
- Oceanfront Home w/Private Pool. USA Military & Fire - Repeat Guest Discount!
- Volcano Rainforest Estate & Lodge; 5 miles to National Park; Hot Tub; 3 BR/3 BA 11-3203 Huakai Street, Volcano, HI, 96785, US
- Hawaiian Charm.Just Steps From The Ocean.On Kauai's Sunny W Side * TVNC4216
- HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
- Hand Crafted Luxury Home with Jacuzzi & Fireplace
- Private, ocean front home with private pool, Amazing place!
- Fall & Winter Specials!, Weekly Disc. 5 star Reviews! F403 Top Floor 2 BR/3 BA
- Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park
How much does it cost to rent a place to stay near Hawaii in the wintertime?
The average cost for winter rentals in Hawaii is $771 per night. Vacation Cottage has a wide list of great winter places to stay near Hawaii that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Hawaii that allow pets?
Yes, here are the top cottage/chalet rentals in Hawaii that allow you to bring your pet or dog:
- Makena Surf F208 Beachfront Resort - 2 Bedroom Oceanfront Condo
- Volcano Teapot Cottage
- Holualoa Inn
- Makena Surf B106 Beachfront Resort - 2 Bedroom Oceanfront Condo
See all pet-friendly vacation rentals in Hawaii on Vacation Cottage
Do you have any winter rentals in Hawaii that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Hawaii to find what works for you.
Are there winter accommodations in Hawaii that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 28660 private swimming pools or indoor pools accommodations near Hawaii along with other great amenities.
Do any winter holiday rentals in Hawaii have hot tubs?
About 28660 holiday rentals in Hawaii boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Hawaii?
Yes, there are many luxury places to stay in Hawaii for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Hawaii with all the best amenities for your next trip.
