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  2. Windward Coast
  3. Oceanfront Vacation Rentals

Windward Coast Oceanfront Vacation Rentals

10.0 (158 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
|
8.3 (502 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly

Why Choose Rent By Owner for your Windward Coast Oceanfront Vacation Rentals?

What makes our Oceanfront Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Windward Coast

When should you plan your Oceanfront Vacation Rentals stay?

Timing your visit to this coastal destination can significantly enhance your experience, so consider planning your vacation during the region’s optimal seasons when the weather is most favorable for enjoying the stunning oceanfront rentals here.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll experience ideal weather for enjoying the region’s beautiful beaches and outdoor activities, making it the most popular time to visit.

Average Temperature Daytime: mid 80s to low 90s Fahrenheit - Nighttime: high 60s to mid 70s Fahrenheit
autumn
Fall (September to November)

Autumn offers pleasant weather and fewer crowds, perfect for exploring and relaxing in oceanfront rentals while the scenery transitions into vibrant fall colors.

Average Temperature Daytime: high 70s to mid 80s Fahrenheit - Nighttime: mid 50s to mid 60s Fahrenheit

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures and less tourist activity, providing a peaceful atmosphere for those seeking quiet oceanfront retreats.

Average Temperature Daytime: mid 50s to low 60s Fahrenheit - Nighttime: mid 40s to low 50s Fahrenheit
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Spring (March to May)

Spring offers mild weather and blooming landscapes, making it an ideal time for travelers looking to enjoy the region’s natural beauty without the peak-season crowds.

Average Temperature Daytime: mid 60s to high 70s Fahrenheit - Nighttime: mid 40s to mid 50s Fahrenheit

Weekly Weather Forecast for Windward Coast

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.

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 direct access to the pristine beaches with outdoor seating areas, perfect for soaking up the sun and scenic ocean views.
  • Take advantage of private balconies or verandas that offer panoramic vistas of the coast, ideal for relaxing mornings or sunset evenings.
  • Make the most of outdoor grilling stations to cook up fresh seafood and local delicacies while enjoying the coastal breeze.
  • Benefit from outdoor pools or hot tubs that overlook the water, providing a tranquil setting to unwind after your adventures.
  • Use well-maintained walking paths or garden spaces to explore the region’s natural beauty at your own pace.
  • Utilize on-site sports courts or recreational areas for active outdoor fun amid the scenic surroundings.
  • Relish in outdoor dining setups that allow you to dine al fresco while listening to the soothing sounds of the sea.
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Family Activities

  • Beach Day Activities Spend quality time with your family enjoying the pristine beaches along the Windward Coast, perfect for swimming, sunbathing, and building sandcastles.
  • Nature Exploration Tours Discover the area's rich natural beauty through guided nature tours that highlight local wildlife and scenic coastal views.
  • Family-Friendly Parks Visit nearby parks featuring playgrounds, picnic areas, and open spaces that provide endless fun for children and relaxing spots for parents.
  • Marine Wildlife Watching Embark on boat excursions to observe dolphins, whales, and other marine life unique to this coastal region.
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Adult Activities

  • Scenic Coastal Cruises: Embark on a leisurely cruise along the coastline to enjoy breathtaking views of the ocean and the surrounding scenery while spotting local wildlife.
  • Beachside Yoga Sessions: Participate in rejuvenating yoga classes held directly on the sandy beaches, offering a peaceful environment to connect with nature.
  • Snorkeling Adventures: Explore vibrant marine life just offshore as you discover the colorful underwater world that makes this region a popular destination for water enthusiasts.
  • Local Seafood Tasting Tours Indulge in fresh, locally caught seafood through guided tasting tours that highlight the region’s culinary delights by the sea.

Windward Coast Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Secure your oceanfront rentals well in advance to ensure you find the perfect property that meets your desired amenities and view preferences here on the Windward Coast.
  • Explore Local Beaches: Take advantage of the region's beautiful beaches by scheduling your visits early in the day for a more peaceful experience and stunning sunset views.
  • Discover Hidden Gems: Venture beyond the popular spots and seek out lesser-known coastal areas within this destination to enjoy a more authentic and uncrowded atmosphere.
  • Respect the Environment: Preserve the natural beauty of the area by adhering to local guidelines, especially when enjoying outdoor activities near your oceanfront rental.

Transportation Options

  • Car Rentals Renting a car provides flexible and convenient transportation to explore the area and access your chosen oceanfront rental with ease.
  • Public Transit Local buses and transit services offer affordable options for getting around the region without the hassle of driving.
  • Taxi and Ride-Sharing Taxi services and ride-sharing apps like Uber or Lyft are readily available, offering quick transfers directly to your oceanfront accommodation.
  • Bike Rentals Biking is an eco-friendly choice that allows you to enjoy scenic views while traveling comfortably around this coastal destination.

Local Customs Options

  • Respect for Local Fishing Traditions: It is customary here to observe and honor the region's fishing customs, which are integral to the community’s way of life, especially when visiting local markets or participating in outdoor activities.
  • Celebration of Cultural Festivals: Participating in regional festivals often involves traditional music, dance, and cuisine, offering an authentic experience that connects visitors to the area’s vibrant heritage.
  • Environmental Conservation Practices: The locals place a strong emphasis on preserving the natural beauty of this destination through sustainable practices and respecting protected coastal areas.
  • Greeting Customs: Warm welcomes often include friendly gestures such as handshakes or verbal greetings in the local dialect, reflecting the area's friendly and hospitable community spirit.

Frequently Asked Questions About Windward Coast Oceanfront Rentals

2. How many Oceanfront Rentals are available in Windward Coast?

Currently, the total number of properties listed by RBO in 2026 is over 412 in the Windward Coast area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in Windward Coast. 

3. What is the cancellation policy for oceanfront rentals in this area?

Cancellation policies vary depending on the specific property you choose. It is recommended to review the individual listing details or contact the property owner directly to understand the applicable cancellation terms.

4. Are there any additional fees I should be aware of when booking oceanfront accommodations here?

Additional fees such as cleaning fees, service charges, or security deposits are typically outlined in the listing details. To avoid surprises, please review these fees carefully on the property page or reach out to the host for clarification.

5. How do I secure my booking in this popular coastal region?

You can secure your reservation by completing the booking process through the listing’s online platform, which often includes payment and confirmation steps. For any special requests or questions, contacting the property owner directly may help ensure your reservation is confirmed smoothly.

6. What amenities are typically included with oceanfront rentals in this destination?

Most properties offer a range of amenities such as direct beach access, modern kitchens, Wi-Fi, and private outdoor spaces. Specific features are listed on each property page, so it’s best to review those details before booking.

7. Is it possible to modify or extend my stay after booking an oceanfront rental?

Changes to your reservation depend on the property's availability and the host’s policies. It’s advisable to contact the property owner directly as soon as possible to discuss modification or extension options.

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