Best Vacation Homes in Windward Coast
Bed & Breakfast
10.0(169 Reviews)
1 Bedroom
1 Bath
2 Guests
330 ft²
Ocean View
Balcony/Terrace
View
Kitchen
CA $648/Night
7 Nights - CA $4,539
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
1496.18 ft²
Parking
Internet
Child Friendly
Accessibility
CA $289/Night
7 Nights - CA $2,023
CA $393/Night
7 Nights - CA $2,749
Cottage
10.0(136 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
Oceanfront- Ocean View
- Balcony/Terrace
- View
CA $438/Night
7 Nights - CA $3,069
House
9.2(88 Reviews)
3 Bedrooms
4 Baths
7 Guests
1797.57 ft²
- Oceanfront
- Ocean View
- View
Breakfast
CA $380/Night
7 Nights - CA $2,662
Apartment
10.0(120 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $379/Night
7 Nights - CA $2,655
Apartment
10.0(112 Reviews)
1 Bedroom
1 Bath
2 Guests
280 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $466/Night
7 Nights - CA $3,264
Cottage
10.0(107 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $474/Night
7 Nights - CA $3,316
Windward Coast Luxury Rentals
House
10.0(37 Reviews)
9 Bedrooms
7 Baths
20 Guests
9000 ft²
Private Pool- Oceanfront
Hot Tub
Spa
Unlock the Best Price
House
10.0(3 Reviews)
3 Bedrooms
4 Baths
8 Guests
2888 ft²
- Private Pool
- Oceanfront
Pool- Ocean View
CA $6,573/Night
7 Nights - CA $46,009
House
9.8(76 Reviews)
6 Bedrooms
5 Baths
16 Guests
3759 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $6,444/Night
7 Nights - CA $45,105
House
7 Bedrooms
6 Baths
14 Guests
5902 ft²
- Private Pool
- Oceanfront
- Hot Tub
Fireplace/Heating
CA $6,315/Night
7 Nights - CA $44,209
House
5 Bedrooms
5 Baths
10 Guests
6295 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
CA $6,220/Night
7 Nights - CA $43,539
Villa
10.0(28 Reviews)
5 Bedrooms
5 Baths
15 Guests
4150 ft²
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
CA $5,931/Night
7 Nights - CA $41,520
House
10.0(2 Reviews)
6 Bedrooms
5 Baths
18 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $5,883/Night
7 Nights - CA $41,180
House
10.0(136 Reviews)
5 Bedrooms
4 Baths
14 Guests
3157 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $5,425/Night
7 Nights - CA $37,977
Windward Coast Pet Friendly Vacation Rentals
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
1095 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $530/Night
7 Nights - CA $3,710
House
9.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
139.93 ft²
Private Beach- Oceanfront
- Ocean View
- Balcony/Terrace
CA $1,693/Night
7 Nights - CA $11,849
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
696 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $445/Night
7 Nights - CA $3,114
Cabin
8.4(30 Reviews)
39 Bedrooms
18 Baths
50 Guests
1076.39 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $701/Night
7 Nights - CA $4,908
House
9.8(146 Reviews)
2 Bedrooms
1 Bath
6 Guests
600 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $258/Night
7 Nights - CA $1,805
House
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $398/Night
7 Nights - CA $2,784
Apartment
1 Bedroom
1 Bath
1 Guest
Pet Friendly- Parking
- Internet
- Child Friendly
CA $216/Night
7 Nights - CA $1,513
House
10.0(25 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
CA $490/Night
7 Nights - CA $3,428
Windward Coast Large Vacation Homes
House
10.0(229 Reviews)
5 Bedrooms
5 Baths
14 Guests
4400 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $4,720/Night
7 Nights - CA $33,041
House
5 Bedrooms
2 Baths
10 Guests
1797.57 ft²
- Pool
- Balcony/Terrace
- View
- Parking
CA $3,239/Night
7 Nights - CA $22,672
House
10.0(1 Review)
5 Bedrooms
2 Baths
18 Guests
3500 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $3,874/Night
7 Nights - CA $27,121
House
10.0(35 Reviews)
3 Bedrooms
3 Baths
10 Guests
2000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $5,134/Night
7 Nights - CA $35,936
House
4 Bedrooms
4 Baths
14 Guests
2798.62 ft²
- Pool
- View
- Parking
Air Conditioner
CA $2,614/Night
7 Nights - CA $18,296
House
10.0(34 Reviews)
4 Bedrooms
4 Baths
10 Guests
2700 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,377/Night
7 Nights - CA $9,639
House
10.0(25 Reviews)
7 Bedrooms
3 Baths
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $1,357/Night
7 Nights - CA $9,498
House
10.0(21 Reviews)
5 Bedrooms
5 Baths
14 Guests
3290 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $1,636/Night
7 Nights - CA $11,449
Why Choose Rent By Owner for your Windward Coast Vacation Rental Homes?
What makes our Vacation Rentals 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 Windward Coast Vacation Rentals
Where are the best neighborhoods to stay in Windward Coast?
When exploring Windward Coast, USA, selecting the right neighborhood can enhance your vacation experience. Each area offers unique characteristics, from vibrant coastal communities to serene residential streets, providing a perfect backdrop for your stay. Whether you're seeking easy access to local beaches or a quieter retreat, you'll find neighborhoods that suit your preferences. Booking a vacation rental in Windward Coast allows you to enjoy the comfort and convenience of a home away from home, with trusted options available throughout the region. Discover the ideal neighborhood to make your visit memorable and seamless.
Hawaii Kai
Located along the southeastern coast, this area offers a relaxed atmosphere with easy access to scenic waterways and lush landscapes, making it an ideal base for exploring the region.
View 70+ Rentals in Hawaii KaiEastern Honolulu
Known for its vibrant community and stunning ocean views, this part of the city provides convenient proximity to local attractions while maintaining a peaceful ambiance.
View 160+ Rentals in Eastern HonoluluLanikai
Famous for its pristine beaches and calm waters, this neighborhood is perfect for enjoying tranquil seaside escapes in the region.
View 63+ Rentals in LanikaiCoconut Grove
Offering a charming residential setting near the coastline, this area provides a comfortable environment for those seeking a laid-back vacation experience.
View 499+ Rentals in Coconut GroveKalama Tract
Nestled close to the beach, this neighborhood features spacious homes and easy access to outdoor activities, making it a popular choice for travelers.
View 113+ Rentals in Kalama TractKamehame Ridge
Perched above the city, this area offers panoramic views and a peaceful retreat while still being close to the city's amenities.
View 164+ Rentals in Kamehame RidgeKuulei Tract
Situated near the water's edge, this neighborhood provides serene surroundings and quick access to Kailua's vibrant community life.
View 483+ Rentals in Kuulei TractEnchanted Lake
Centered around a picturesque lake, this area offers a quiet and scenic environment that is perfect for relaxing getaways in the region.
View 456+ Rentals in Enchanted LakeBest Times to Visit Windward Coast
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation here ensures you experience the region's best weather and local events, making your stay more enjoyable and memorable.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you'll experience warm weather ideal for enjoying the coast's outdoor activities and beautiful beaches.
Average Temperature Daytime: around 85°F - Nighttime: around 70°F
Winter Holidays (December to February)
This popular season draws visitors seeking mild winter climates and festive atmosphere along the shorelines, making it a lively time to visit the region.
Average Temperature Daytime: around 75°F - Nighttime: around 60°F
Off-Season Highlights
Spring (March to May)
The shoulder season features pleasant weather and fewer crowds, allowing you to explore the area's natural beauty comfortably.
Average Temperature Daytime: around 70°F - Nighttime: around 55°F
Fall (September to November)
In autumn, the region offers cooler temperatures and vibrant scenery, providing an excellent opportunity for relaxation away from the high season rush.
Average Temperature Daytime: around 75°F - Nighttime: around 58°F
Weekly Weather Forecast for Windward Coast
How to Book Your Windward Coast Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Windward Coast
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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 outdoor lounging areas such as patios or decks with scenic views of the surrounding landscape.
- Take advantage of private or shared swimming pools to relax and cool off during your stay.
- Make use of spacious yards or gardens ideal for outdoor activities and family gatherings.
- Benefit from direct access to nearby beaches or waterfronts, perfect for water-based recreation.
- Utilize outdoor grilling stations or barbecue areas to enhance your alfresco dining experience.
- Experience outdoor showers or hot tubs that offer a soothing retreat after a day of exploring.
- Comprehend the convenience of tennis courts, golf courses, or other sports facilities often available nearby.
Top Attractions Around Windward Coast
What attractions are nearby?
Within this vibrant area, you can enjoy a variety of outdoor activities, cultural experiences, and scenic excursions that highlight the natural beauty and local charm of Windward Coast, USA.
Family Activities
- Beach Activities: Spend quality time with your family exploring the pristine shores of this destination, where swimming, building sandcastles, and beachcombing are popular pastimes.
- Marine Aquarium Tour: Discover local marine life at the area's renowned aquarium, offering engaging exhibits that are both educational and entertaining for all ages.
- Nature Trails and Parks: Take advantage of scenic hiking trails and parks that wind through the region, providing excellent opportunities for outdoor adventures and wildlife spotting.
- Family-Friendly Cruises: Enjoy a relaxing boat cruise along the coast, perfect for experiencing the area's natural beauty from a different perspective while creating unforgettable memories.
Adult Activities
- Explore Local Art Galleries: Discover vibrant art scenes and unique galleries that showcase the region's creative spirit, perfect for relaxing afternoons.
- Enjoy Water Sports and Beach Activities: Take advantage of the pristine beaches by engaging in surfing, paddleboarding, or simply relaxing along the shoreline.
- Visit Cultural Heritage Sites: Immerse yourself in the area's history and traditions by exploring well-preserved heritage sites and museums.
- Experience Fine Dining and Local Cuisine: Savor diverse culinary offerings at acclaimed restaurants that highlight the region’s fresh seafood and local flavors.
Other Places to Stay in Windward Coast, HI
Coconut Grove
Kuulei Tract
Enchanted Lake
Keolu Hills
Kailua
Waimanalo
Waimanalo Beach
Kalama Tract
Kahalu u
Lanikai
Ka'a'awa
Kaneohe
Windward Coast Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Flavors: Take advantage of the region's renowned culinary scene by visiting local eateries and markets to experience authentic regional cuisine during your stay.
- Plan Outdoor Activities: Make the most of the area's natural beauty by scheduling outdoor adventures such as hiking, beach outings, or boat trips that showcase its scenic landscapes.
- Discover Hidden Gems: Talk to hosts or locals to find lesser-known attractions and secret spots that offer a more personalized and memorable experience here.
- Optimize Your Accommodation Choice: Choose well-reviewed vacation rentals that provide comfort and amenities aligned with your needs, ensuring a relaxing and enjoyable visit to this destination.
Transportation Options
- Private Car Rentals: Exploring the area at your own pace is easiest with private vehicle rentals, offering flexibility to visit hidden beaches and scenic spots nearby.
- Public Transit Services: Local bus routes connect key destinations across this destination, providing an affordable way to navigate without the hassle of parking.
- Taxi and Rideshare Options: Taxis and rideshare services like Uber or Lyft are readily available here, ensuring convenient transfers to popular attractions and your vacation rental.
- Bicycle Rentals: For a more active approach, renting a bicycle allows you to enjoy the coastal views and local neighborhoods at a leisurely pace.
Local Customs Options
- Respect for the Sea: Locals take pride in their maritime traditions, and you’ll notice this through their customs of greeting and serving seafood with reverence.
- Festivals and Celebrations: Participating in local festivals offers an authentic experience of the region’s vibrant culture and deep-rooted community spirit.
- Traditional Arts and Crafts: Visitors can observe or purchase handcrafted items that showcase the region’s artistic heritage and skilled craftsmanship.
- Community Hospitality: Expect genuine warmth and friendliness from residents who value forging meaningful connections with newcomers.
Frequently Asked Questions About Windward Coast?
1. What are the top vacation rentals in Windward Coast?
There are a lot of options in Windward Coast. If you plan on staying in the Windward Coast area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windward Coast:
- Place in Paradise-Summer Available -Short term Lic#1990/NUC-1802
- PRIVATE BEACHFRONT RENTAL
- Secluded Home w/Pool in Gated Community, Steps From Beautiful Kailua Beach
- Walker Beach House - Lanikai Ocean Front Lic.#1990/NUC-1757
- Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
- 'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
- Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
- Kailua Oceanfront Villa with Heated Pool & Spa
- Available and legal for stays less than 30 days.
- Makapu’u Hale, Literally oceanfront! VIEWS! A/C, 2 bedroom/2 bath
2. How many vacation rentals have private pools in Windward Coast?
There are 103 vacation rentals with private pools near Windward Coast. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windward Coast are best for families?
If you are looking for a family-friendly vacation home in Windward Coast, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windward Coast:
4. How many Rentbyowner vacation rentals are available in Windward Coast?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 607 in the Windward Coast area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windward Coast.
5. What is the cancellation policy for vacation rentals in Windward Coast?
Cancellation policies vary depending on the individual property owner. It's recommended to review the specific listing details or contact the host directly to understand the terms and conditions related to cancellations.
6. How do I confirm my reservation at a vacation rental in Windward Coast?
Reservations are confirmed once you complete the booking process and receive a confirmation email from the platform. Always double-check the details and contact the host if you have any questions before your arrival.
7. Are there any additional fees associated with booking a vacation rental in this region?
Additional fees such as cleaning, service charges, or taxes may apply depending on the property. These fees are typically listed during the booking process, but it's best to review the breakdown or contact the host for clarification.
8. What should I know about checking in and check-out procedures at Windward Coast vacation rentals?
Check-in and check-out procedures are outlined in each listing. Many hosts offer self-check-in options, but it’s advisable to communicate with your host beforehand to ensure smooth arrival and departure times.
9. Is it possible to modify or extend my stay at a vacation rental in the area?
Modifications or extensions depend on the property's availability and the host’s policies. Contact the host directly through the platform to request changes and confirm whether they can accommodate your new travel plans.
Windward Coast Top Rated Vacation Rentals
House
10.0(152 Reviews)
4 Bedrooms
4 Baths
8 Guests
2600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,463/Night
7 Nights - CA $10,242
House
10.0(116 Reviews)
4 Bedrooms
4 Baths
8 Guests
3200 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $939/Night
7 Nights - CA $6,569
House
10.0(112 Reviews)
3 Bedrooms
4 Baths
6 Guests
3400 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $982/Night
7 Nights - CA $6,872
House
10.0(99 Reviews)
4 Bedrooms
3 Baths
8 Guests
2000 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
CA $1,132/Night
7 Nights - CA $7,924
House
10.0(91 Reviews)
4 Bedrooms
3 Baths
8 Guests
2200 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $2,371/Night
7 Nights - CA $16,595
House
10.0(62 Reviews)
3 Bedrooms
2 Baths
7 Guests
2700 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,266/Night
7 Nights - CA $8,862
House
10.0(57 Reviews)
3 Bedrooms
3 Baths
6 Guests
2000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $690/Night
7 Nights - CA $4,826
House
10.0(45 Reviews)
1 Bedroom
1 Bath
5 Guests
498 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $353/Night
7 Nights - CA $2,469
