Winter Rentals in Waikiki:【 GREAT PRICES 】Rent By Owner

Waikiki Winter Rental

New

Condo

Wyndham at Waikiki Beach Walk - 2 Bedroom Condo

2 Bedrooms 2 Baths 8 Guests

R9,170/Night 7 Nights - R64,189

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Diamond Head Dreams Beach Condo with Ocean View!

Apartment

Diamond Head Dreams Beach Condo with Ocean View!

10.0

Exceptional

(6 Reviews)

1 Bedroom 1 Bath 4 Guests 602.78 ft²

R6,872/Night 7 Nights - R48,104

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Waikiki Banyan Condo w/King Bed & Parking, Near Beach

Price Dropped

Apartment

Waikiki Banyan Condo w/King Bed & Parking, Near Beach

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 4 Guests

R8,001/Night 7 Nights - R56,015

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30FL Partial Ocean View with Lanai, Wi-Fi, & Parking

New

Condo

30FL Partial Ocean View with Lanai, Wi-Fi, & Parking

1 Bedroom 1 Bath 4 Guests 600 ft²

R7,255/Night 7 Nights - R50,791

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Stylish Ocean View Condo Near Waikiki Beach with Free Parking!

Apartment

Stylish Ocean View Condo Near Waikiki Beach with Free Parking!

10.0

Exceptional

(5 Reviews)

1 Bedroom 1 Bath 4 Guests 602.78 ft²

R4,894/Night 7 Nights - R34,261

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Waikiki Seaside Luxury King Condo with Balcony

New

Apartment

Waikiki Seaside Luxury King Condo with Balcony

1 Bedroom 1 Bath 3 Guests

R5,913/Night 7 Nights - R41,381

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Freshly Updated Condo in Waikiki with Free Parking

Top 10% in Waikiki

Apartment

Freshly Updated Condo in Waikiki with Free Parking

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 602.78 ft²

R8,839/Night 7 Nights - R61,882

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New

Apartment

Ocean View Waikiki Hawaiian Monarch

1 Bedroom 1 Bath 2 Guests

R5,219/Night 7 Nights - R36,536

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Chic and Upscale Waikiki Beach Ocean View with Parking

Apartment

Chic and Upscale Waikiki Beach Ocean View with Parking

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 602.78 ft²

R7,190/Night 7 Nights - R50,329

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29th floor ocean view Waikiki Hawaiian Monarch

New

Apartment

29th floor ocean view Waikiki Hawaiian Monarch

1 Bedroom 1 Bath 2 Guests

R4,532/Night 7 Nights - R31,724

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36th Floor Deluxe Ocean View Condo with Free Parking & Wifi condo

Apartment

36th Floor Deluxe Ocean View Condo with Free Parking & Wifi condo

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 538.2 ft²

R6,943/Night 7 Nights - R48,599

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@ Marbella Lane- Trendy Waikiki Oasis | Near Beach

Price Dropped

House

@ Marbella Lane- Trendy Waikiki Oasis | Near Beach

1 Bedroom 1 Bath 4 Guests

R4,133/Night 7 Nights - R28,938

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More Top-Rated Winter Rental in Waikiki Area

Why Choose Rent By Owner for your Waikiki 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.

Popular Areas for Waikiki Winter Rental

Where are the best neighborhoods to stay in Waikiki?

When seeking the perfect Waikiki neighborhood to stay in during your visit to Honolulu, you'll find that areas close to the beach offer stunning ocean views and convenient access to local attractions. The vibrant heart of Waikiki is ideal for those wanting a lively atmosphere with plenty of dining and shopping options, while more relaxed neighborhoods provide a serene retreat with easy access to parks and cultural sites. No matter your preference, choosing a well-located area ensures an authentic Hawaiian experience during your winter stay.

Diamond Head - Kapahulu - St. Louis

Staying in this area places you close to iconic views and vibrant local culture, making it ideal for experiencing authentic island life during your winter stay. It offers convenient access to scenic spots and lively neighborhoods, perfect for exploring the region's natural beauty.

View 118+ Rentals in Diamond Head - Kapahulu - St. Louis

McCully - Moiliili

Located nearby bustling shopping and dining options, this neighborhood provides a lively atmosphere that complements your winter getaway. Here, you can enjoy easy access to local markets and cultural experiences, enriching your stay in the region.

View 94+ Rentals in McCully - Moiliili

Best Times to Visit Waikiki

When should you plan your Winter Rental stay?

To make the most of your experience here, consider planning your visit during the shoulder seasons to enjoy pleasant weather and fewer crowds while securing ideal winter rentals in this vibrant destination.

Peak Season Highlights

Winter (December to February)

During these months, you’ll experience the peak season in this popular destination, characterized by ideal weather for outdoor activities and vibrant local events, making it a prime time to explore the region.

Average Temperature Daytime: around 80°F - Nighttime: around 65°F

Summer (June to August)

This period marks another high travel season with warm temperatures and lively atmosphere, attracting visitors seeking the perfect summer beach getaway in this tropical destination.

Average Temperature Daytime: around 88°F - Nighttime: around 75°F

Off-Season Highlights

Spring (March to May)

In spring, fewer crowds and mild weather create an appealing time to enjoy quiet relaxation while still benefiting from comfortable daytime temperatures.

Average Temperature Daytime: around 82°F - Nighttime: around 67°F

Fall (September to November)

Autumn offers a more tranquil experience with pleasant weather and lower rates, ideal for those looking to avoid the busy seasons while enjoying the beauty of this coastal area.

Average Temperature Daytime: around 85°F - Nighttime: around 70°F

Weekly Weather Forecast for Waikiki

How to Book Your Waikiki 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

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Waikiki

More Top-Rated Winter Rental in Waikiki Area

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

Outdoor Amenities

Enjoy access to a sparkling outdoor swimming pool to relax after a day exploring the region.
Take advantage of well-maintained outdoor lounging areas perfect for soaking up the sun and panoramic ocean views.
Benefit from lush landscaped gardens that provide a tranquil setting right outside your door.
Utilize on-site barbecue grills to host memorable cookouts in a scenic outdoor environment.
Make use of shared outdoor terraces or decks designed for socializing with fellow guests or enjoying the sunset.
Stay active with outdoor fitness facilities that allow you to maintain your workout routine while on vacation.
Access nearby outdoor recreational options such as beach access points, ideal for surfing, swimming, or simply unwinding by the shoreline.

Top Attractions Around Waikiki

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of activities such as surfing along iconic beaches, exploring lush hiking trails, and experiencing the lively local culture-all conveniently accessible from your nearby Waikiki winter rentals, making it an ideal destination for your Hawaii getaway.

Family Activities

Waikiki Beach Activities: Spend a day relaxing and building sandcastles on the iconic Waikiki Beach, perfect for family fun in the sun.
Honolulu Zoo: Explore a variety of exotic animals at the Honolulu Zoo, offering an educational experience for children and adults alike.
Starlight Luau Shows: Enjoy a traditional Hawaiian luau featuring Polynesian music, dance, and cuisine that creates unforgettable family memories.
Sea Life Park Hawaii: Discover marine life exhibits and interactive encounters at this popular attraction, ideal for engaging children's curiosity about ocean ecosystems.

Adult Activities

Sunset Catamaran Cruises: Experience a relaxing evening on the water as you enjoy spectacular views of the sunset along the picturesque coastlines.
Elegant Dinners at Beachfront Restaurants: Indulge in gourmet Hawaiian cuisine while savoring oceanfront vistas that showcase the region’s vibrant culinary scene.
Spa and Wellness Retreats: Recharge with rejuvenating treatments at luxury spas that reflect the soothing ambiance of this tropical destination.
Nightlife and Live Entertainment: Explore the lively bars and venues offering live music and entertainment, perfect for unwinding after a day of adventure here.

Other Places to Stay in Waikiki, HI

Waikiki Beach Walk

Explore 8,514 Properties

Royal Hawaiian Center

Explore 8,510 Properties

U.S. Army Museum of Hawai'i

Explore 8,508 Properties

Gray's Beach

Explore 8,504 Properties

Kawehewehe

Explore 8,503 Properties

International Market Place

Explore 8,502 Properties

Fort DeRussy

Explore 8,498 Properties

Fort DeRussy Beach Park

Explore 8,498 Properties

Royal-Moana Beach

Explore 8,486 Properties

Fort DeRussy Beach

Explore 8,481 Properties

Duke Kahanamoku Beach

Explore 8,476 Properties

Honolulu Zoo

Explore 8,470 Properties

More Places to Stay Near Waikiki

Waikiki Travel Tips

How Can You Make the Most of Your Stay?

Embrace the Local Culture: Take time to explore traditional Hawaiian customs and attend local events to enrich your experience.
Plan Your Beach Days: Make the most of the region’s stunning beaches by visiting early in the morning or late afternoon to avoid crowds and enjoy the tranquil atmosphere.
Use Public Transportation: Maximize convenience and reduce transportation costs by utilizing the area's bus services and shuttle options available nearby.
Savor Authentic Cuisine: Sample regional delicacies at local eateries to immerse yourself in the flavors that define this destination’s culinary scene.

Transportation Options

Public Bus System (TheBus): This affordable transit option provides comprehensive coverage of the region, making it easy for you to explore here without needing a vehicle.
Shuttle Services: Convenient shuttle options connect major hotels and popular attractions, offering a hassle-free way to navigate the area.
Rental Cars: Renting a car gives you flexibility and independence to discover hidden gems and scenic spots beyond the usual routes here.
Bike Rentals: For an eco-friendly and healthy way to experience the destination, bike rentals are widely available and ideal for shorter distances around this vibrant locale.

Local Customs Options

Respect for Aloha Spirit: Embracing the Aloha Spirit is essential here, emphasizing kindness, respect, and harmony in daily interactions.
Traditional Hawaiian Greetings: Greeting others with a gentle handshake or a bow reflects the region's cultural customs rooted in greeting and showing hospitality.
Honoring Sacred Sites: Visiting and respecting sacred places entails following local guidelines and refraining from disruptive behavior at historical and spiritual sites.
Practicing Eco-friendly Etiquette: Participating in conservation efforts by disposing of waste properly and avoiding damage to natural surroundings preserves the area’s pristine beauty.

Frequently Asked Questions About Waikiki Winter Rentals

1. What are the top Winter Rentals in Waikiki?

There are a lot of options in Waikiki. If you plan on staying in the Waikiki area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Winter Rentals in Waikiki:

2. How many Winter Rentals are available in Waikiki?

Currently, the total number of properties listed by RBO in 2026 is over 3631 in the Waikiki area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Waikiki. 

3. What is the cancellation policy for winter rentals in Waikiki, Honolulu?

The cancellation policy varies depending on the property listing. You should review the specific terms listed on the property page or contact the owner directly to understand any fees, refund eligibility, and deadlines.

4. How do I ensure my booking for a winter rental is secure and confirmed?

Your reservation is typically secured once you complete the booking process and receive confirmation from the owner. It’s recommended to verify all details and communicate through the platform's messaging system to confirm your stay.

5. Are there any special requirements or restrictions for winter rentals in this area?

Restrictions such as minimum stay periods, age limits, or occupancy limits are detailed in each listing. Review the property description carefully and reach out to the owner if you have specific questions about amenities or policies.

6. What amenities are usually included with winter rentals in this destination?

Most listings include essential amenities like Wi-Fi, kitchen facilities, air conditioning, and parking. For additional features such as pool access or laundry services, check the individual property details or contact the host.

7. How can I find the best winter rental deals in this region?

To secure the best deals, compare listings, read reviews, and consider flexible dates. Use filters on the platform to sort by price, amenities, and guest ratings, and contact owners for any special offers or discounts.