Hawaii Winter Rental
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Parking
US $813/Night
For 7 Nights US $5,690
1001.04 ft²
2 Guests
6 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
US $225/Night
For 7 Nights US $1,575
US $843/Night
For 7 Nights US $5,904
3600 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $648/Night
For 7 Nights US $4,533
979.52 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $817/Night
For 7 Nights US $5,716
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Internet
US $499/Night
For 7 Nights US $3,496
US $289/Night
For 7 Nights US $2,023
1499 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
US $750/Night
For 7 Nights US $5,248
US $795/Night
For 7 Nights US $5,565
2489 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Pool
- Balcony/Terrace
US $1,081/Night
For 7 Nights US $7,570
3498.27 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- View
US $729/Night
For 7 Nights US $5,102
1589 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Spa
- Pool
US $1,073/Night
For 7 Nights US $7,510
Why Choose Rent By Owner for your Hawaii Winter Rental?
What makes our Winter Rental special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Hawaii
How to Book Your Hawaii Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Hawaii
Common Winter Rental Amenities
What amenities can you expect?
Our Winter Rental are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Hawaii, HI
Maui County
West Maui
Lahaina
Honolulu County
Hawaii Island
South Maui
Kona Coast
Kauai County
Hawaii Winter Rental Frequently Asked Questions
1. What are the top 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
- 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
- Oceanfront Home w/Private Pool. USA Military & Fire - Repeat Guest Discount!
- 'Aloha!' Perfect Location Near Beach & Turtle Bay Resort, File # 1990/NUC- 1964
- HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
- 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
- Private, ocean front home with private pool, Amazing place!
- Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park
2. How many Winter Rentals are available in Hawaii?
Currently, the total number of properties listed by RBO in 2026 is over 30368 in the Hawaii area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Hawaii.
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6 Guests
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- Hot Tub
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3 Bedrooms
3 Bathrooms
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- Hot Tub
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- Oceanfront
- Hot Tub
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1209 ft²
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2 Bathrooms
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- Hot Tub
- Fireplace/Heating
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1227 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Pool
- Kitchen
- Internet
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943 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
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1156 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
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- Hot Tub
- Pool
- Balcony/Terrace
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492 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
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- Hot Tub
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- Kitchen
- Internet
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