Discover Your Perfect Windward Vacation Homes

Best Vacation Homes in Windward

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Windward Luxury Rentals

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Windward Pet Friendly Vacation Rentals

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Windward Large Vacation Homes

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Why Choose Rent By Owner for your Windward Vacation Rental Homes?

What makes our 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.

Popular Areas for Windward Vacation Rentals

Where are the best neighborhoods to stay in Windward?

When choosing where to stay in Windward, Placida, Florida, you’ll discover a variety of neighborhoods that cater to different preferences and lifestyles. The area offers charming residential communities with easy access to the serene waterfront views and natural beauty that make Placida a sought-after destination. Whether you prefer a peaceful setting close to local amenities or a more active neighborhood with convenient access to outdoor activities, each neighborhood provides a reliable and well-connected base for your Florida vacation. With thoughtfully located vacation rentals, your stay in Windward can be both comfortable and memorable, ensuring a seamless experience from booking to check-out.

Cape Haze

In this part of Placida, you'll find peaceful surroundings and easy access to outdoor activities, making it an ideal spot for a relaxing getaway. Staying here places you close to scenic views and quiet streets, perfect for unwinding during your vacation.

View 56+ Rentals in Cape Haze

Best Times to Visit Windward

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here ensures you experience the region's best weather and activities, making your stay in Windward, Placida, Florida even more memorable and enjoyable.

Peak Season Highlights

spring
Spring (March to May)

This is the most popular time to visit the area, as the weather is warm and ideal for outdoor activities. Expect higher occupancy rates for vacation rentals during this period.

Average Temperature Daytime: Approximately 75-85°F - Nighttime: Around 60-70°F
winter
Winter (December to February)

The region becomes a favored winter escape, attracting visitors seeking mild temperatures and sunny days. Booking your vacation rentals early ensures the best selection in this busy season.

Average Temperature Daytime: Approximately 70-80°F - Nighttime: About 50-60°F

Off-Season Highlights

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Summer (June to August)

While the summer months see fewer visitors, you can enjoy more flexible booking options and quieter surroundings at your vacation rentals here.

Average Temperature Daytime: Generally 85-90°F - Nighttime: Roughly 70-75°F
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Fall (September to November)

The area experiences a slowdown in travel, making it an excellent time for those seeking a more tranquil stay at vacation rentals with fewer crowds.

Average Temperature Daytime: Around 75-85°F - Nighttime: Approximately 55-65°F

Weekly Weather Forecast for Windward

How to Book Your Windward 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

More Top-Rated Vacation Rentals in Windward Area

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 living with access to a private screened lanai or patio, perfect for relaxing after a day exploring the area.
  • Take advantage of a sparkling swimming pool, ideal for cooling off and unwinding under the Florida sun.
  • Make use of outdoor grilling facilities to host a barbecue and savor fresh seafood or local produce.
  • Benefit from lush landscaped gardens or yards that provide a peaceful setting for outdoor activities.
  • Experience waterfront views or direct access to nearby canals, enhancing your outdoor experience in this region.
  • Utilize community amenities such as tennis courts or shuffleboard areas, commonly available in this destination’s accommodations.
  • Relax in hammock setups or outdoor lounge chairs designed for enjoying the warm Florida weather outside your rental.

Top Attractions Around Windward

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic nature trails that highlight the region’s coastal beauty.

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Family Activities

  • Fishermen's Village: You can enjoy a day of outdoor shopping, dining, and entertainment at this popular waterfront destination, perfect for family outings in the area.
  • South Gulf Cove Park: Spend quality time outdoors with your loved ones at this scenic park featuring playgrounds, picnic areas, and walking trails along the region's beautiful waterways.
  • Pine Island Nature Preserve: Explore the natural beauty of the region through guided hikes and wildlife observation opportunities suitable for all ages.
  • Local Beaches: Relax on the pristine sands and take advantage of the shallow waters that are ideal for children at various nearby beaches here.
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Adult Activities

  • Fishing Charters and Boat Rentals: Experience the region’s renowned fishing scene by booking a charter or renting a boat to explore the local waters firsthand.
  • Wildlife Watching in Local Reserves: Discover the diverse species of birds and marine life in nearby nature reserves, offering a peaceful retreat into the area's natural beauty.
  • Kayaking and Paddleboarding: Enjoy the calm waters with a leisurely paddle or kayak session, perfect for exploring hidden coves and shoreline areas around here.
  • Golfing at Scenic Courses: Tee off at select golf courses known for their stunning views and challenging play, ideal for a relaxing day on the links in this destination.

Windward Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Water Activities:** Take advantage of the region's beautiful coastal waters by scheduling boating, fishing, or kayaking excursions to fully enjoy here’s aquatic scenery.
  • Explore Local Dining Options:** Savor fresh seafood and regional cuisine at nearby eateries to experience the authentic flavors that make this destination unique.
  • Visit Nearby Natural Spots:** Use your stay as a chance to discover local parks and natural reserves, perfect for outdoor activities and enjoying the area's lush scenery.
  • Book Early for Peak Seasons:** Secure your preferred vacation rentals well in advance during popular travel periods to ensure a seamless and enjoyable visit here.

Transportation Options

  • Rental Cars: You can easily rent a vehicle in the area to explore nearby beaches and attractions with flexibility and comfort.
  • Local Taxis and Rideshare Services: Taxis and ride-hailing options are readily available for convenient, door-to-door transportation around this destination.
  • Public Transit: The regional public transportation system provides an economical way to get around here without the hassle of parking.
  • Boat Charters and Water Taxis: Enjoy scenic water travel using boat charters and water taxis that connect you to surrounding islands and coastal spots.

Local Customs Options

  • Respect for the Local Fishing Traditions: Engaging in or observing local fishing practices is highly regarded, as they are a vital part of the area's culture and economy.
  • Celebration of Seafood Cuisine: You will find that seafood plays a central role in local gatherings, making it customary to enjoy fresh catches during community events and meals.
  • Adherence to Marine Conservation Practices: Preserving the region’s natural beauty involves respecting protected waters and adhering to guidelines on sustainable boating and fishing activities.
  • Greeting with Warmth and Hospitality: Expect a friendly attitude from residents and fellow visitors, reflecting the welcoming spirit prevalent throughout this coastal destination.

Frequently Asked Questions About Windward?

1. What are the top vacation rentals in Windward?

There are a lot of options in Windward. If you plan on staying in the Windward 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:

2. How many vacation rentals have private pools in Windward?

There are 385 vacation rentals with private pools near Windward. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Windward are best for families?

If you are looking for a family-friendly vacation home in Windward, 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:

4. How many Rentbyowner vacation rentals are available in Windward?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1037 in the Windward 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. 

5. What is the cancellation policy for vacation rentals in this region?

Cancellation policies vary depending on the property owner. It's recommended to review the specific listing details or contact the host directly to understand the terms and any possible fees associated with cancellations.

6. Are there any specific check-in and check-out times I should be aware of when booking here?

Check-in and check-out times are typically outlined in each listing. Be sure to review these details before confirming your reservation or reach out to the property owner for clarification to ensure a smooth arrival and departure process.

7. How do I find the most suitable vacation rental in this destination?

To find the best accommodation, filter your search based on your preferred amenities, location proximity, and travel dates. Reading guest reviews and checking the property’s ratings can also help you choose a rental that meets your needs.

8. Are pets allowed in vacation rentals here?

Policies regarding pets differ among properties. You should check the individual listing for pet-friendly options or contact the owner directly to confirm whether bringing a pet is permitted during your stay.

9. What should I do if I encounter issues during my stay at a rental property?

If you experience any problems, contact the property owner or manager promptly through the messaging platform provided. For unresolved issues, consult the listing’s support or help section for further assistance.

Windward Top Rated Vacation Rentals

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