1. USA
  2. Windward Coast
  3. Summer Rental

Windward Coast Summer Rental

10.0 (158 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
|
8.8 (1012 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Why Choose Rent By Owner for your Windward Coast Summer Rental?

What makes our Summer Rental 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 Summer Rental stay?

Choosing the optimal time to enjoy your summer rentals in this destination can ensure you experience ideal weather and avoid peak crowds, allowing you to fully relax and make the most of your stay along the Windward Coast, USA.

Peak Season Highlights

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Summer (June to August)

During the peak summer months, you can enjoy warm temperatures and lively beach days along this coastal area, making it an ideal time for summer rentals to experience the region’s vibrant oceanfront atmosphere.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 65°F to 75°F
autumn
Fall (September to November)

Early fall offers pleasant weather with fewer crowds, providing a more relaxed environment for those booking summer rentals to explore the scenic coastline and enjoy mild evenings in this popular destination.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F

Off-Season Highlights

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Winter (December to February)

With cooler temperatures and quieter beaches, winter presents a peaceful retreat for travelers seeking cozy accommodations and a calm coastal experience away from the busy season.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 45°F to 55°F
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Spring (March to May)

As the region awakens from winter, spring is perfect for exploring the scenic surroundings with milder weather and fewer visitors, offering an excellent opportunity for quieter summer rental stays.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 50°F to 60°F

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 outdoor grilling facilities to prepare meals with fresh local ingredients.
  • Relax by a private or shared swimming pool, perfect for cooling off during warm summer days.
  • Take advantage of spacious patios or decks ideal for outdoor dining and social gatherings.
  • Discover lush gardens or landscaped yards that enhance the scenic beauty of your stay.
  • Make use of outdoor fire pits for cozy evenings under the stars.
  • Utilize nearby walking or biking paths for exploring the natural surroundings.
  • Participate in water sports or beach activities if your rental is close to the coast.
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Family Activities

  • Beach Day at Paradise Beach Spend a relaxing day on the pristine sands and gentle waves, perfect for building sandcastles or just soaking up the sun with your family.
  • Exploring Marine Life at Oceanic Aquarium Discover vibrant sea creatures and interactive exhibits that will captivate children and adults alike, making it an engaging family activity in this scenic area.
  • Hiking at Coastal Trails Park Enjoy scenic views and fresh air while exploring family-friendly trails along the coastline that are ideal for all skill levels.
  • Water Sports Adventures Try kayaking, paddleboarding, or snorkeling in the calm waters of this region, offering fun and safe activities suitable for the entire family.
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Adult Activities

  • Wine Tasting Tours Explore the local wineries along the coast and indulge in guided tastings that showcase regional flavors.
  • Beachside Water Sports Engage in activities such as paddleboarding, jet skiing, or surfing on the pristine shores of the area.
  • Scenic Coastal Cruises Take a boat tour to enjoy breathtaking views of the coastline and observe marine life native to this destination.
  • Gourmet Dining Experiences Savor fresh seafood and regional cuisine at acclaimed restaurants offering stunning ocean vistas.

Windward Coast Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Arrival Early: Secure your preferred summer rentals by booking well in advance to ensure availability during peak season in the Windward Coast area.
  • Explore Local Dining Options: Take advantage of nearby eateries and fresh local markets to truly experience the regional cuisine and support local businesses.
  • Discover Outdoor Activities: Engage in outdoor pursuits like hiking or water sports to make the most of the area's natural beauty and scenic landscapes.
  • Respect the Environment Follow eco-friendly practices to preserve the region's pristine environment for future visitors and enjoy a sustainable stay here.

Transportation Options

  • Car Rentals: Renting a car offers you the flexibility to explore the region at your own pace, making it easy to access your preferred summer rentals and local attractions along the coast.
  • Public Transit: Buses and regional transit services provide an affordable, eco-friendly way to navigate this area without the hassles of parking or traffic.
  • Ride-Sharing Services: Apps like Uber and Lyft operate throughout here, offering convenient transportation options for quick trips or last-minute plans around town.
  • Airport Transfers: Shuttle services and private transfers connect travelers directly from nearby airports to the summer rentals, ensuring a smooth start to your stay in the region.

Local Customs Options

  • Beach Etiquette: Respect for local beaches is essential, including observing designated swimming areas and refraining from littering to preserve the natural beauty of this coastal region.
  • Festive Celebrations: Participating in community festivals and events showcases the area's vibrant culture and offers an authentic experience during your stay.
  • Respect for Local Artisans: Supporting local artisans by purchasing handcrafted goods ensures the preservation of traditional crafts unique to this destination.
  • Environmental Conservation: Embracing eco-friendly practices, such as reducing waste and conserving water, helps maintain the region’s pristine environment for future visitors.

Frequently Asked Questions About Windward Coast Luxury Rentals

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

Currently, the total number of properties listed by RBO in 2026 is over 579 in the Windward Coast area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Summer Rentals in Windward Coast. 

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

Cancellation policies for properties vary depending on the owner’s terms. You should review the specific listing details and contact the host directly to understand any fees, timeframes, or refunds associated with cancellations.

4. How do I find summer rentals that allow pets in this region?

Many listings specify whether pets are permitted. Use the filter options on the booking site to narrow down your search to pet-friendly properties, and always confirm pet policies with the property owner before booking.

5. Are there any specific check-in or check-out procedures I should be aware of for summer rentals here?

Check-in and check-out procedures can differ between properties. It’s recommended to read the detailed instructions provided in the listing or contact the owner directly for any special requirements or timing restrictions.

6. What amenities are typically included in rentals along the coast?

Most properties offer amenities such as Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces. For a comprehensive list, review each listing carefully and reach out to the owner if you have specific needs.

7. How do I inquire about last-minute availability or special offers for summer stays?

You can contact the property owner directly through the booking platform to ask about last-minute openings or promotional rates. It’s often helpful to do so well in advance to secure the best deals.

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