Discover Your Perfect Windward Villa

Windward Villa

More Top-Rated Villa in Windward Area

Why Choose Rent By Owner for your Windward Villa?

What makes our Villa special?

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

Popular Areas for Windward Villa

Where are the best neighborhoods to stay in Windward?

Exploring the neighborhoods in Windward, Placida, Florida offers you a tranquil setting close to stunning waterfront views and pristine beaches. This area provides a peaceful retreat where you can enjoy easy access to local amenities while staying in comfortable villas designed for relaxation. Whether you're seeking a quiet coastal escape or a vibrant community vibe, Windward's neighborhoods are ideal for your next getaway.

Cape Haze

In this area, you'll find a peaceful setting ideal for relaxing getaways, with your choice of charming villas that offer comfort and convenience. Here, the region's natural beauty complements your stay, making it a perfect spot for exploring the scenic surroundings.

View 66+ Rentals in Cape Haze

Best Times to Visit Windward

When should you plan your Villa stay?

Choosing the optimal time to vacation here can enhance your experience in this scenic region, as seasonal weather patterns and local events influence the best periods for relaxation and outdoor activities.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, this coastal destination experiences its busiest season as visitors seek warm escapes and outdoor activities. Booking your villa early ensures you secure a prime spot in this popular period.

Average Temperature Daytime: 75°F - Nighttime: 60°F
spring
Spring (March to May)

Spring brings pleasant weather and blooming landscapes, making it an ideal time to enjoy outdoor leisure here. The region sees increased visitors, so plan ahead for your villa reservation.

Average Temperature Daytime: 78°F - Nighttime: 62°F

Off-Season Highlights

image
Summer (June to August)

The summer months tend to be quieter due to the heat and humidity, providing a more relaxed atmosphere for those seeking tranquility. It's an excellent time for flexible travelers to find favorable villa rates.

Average Temperature Daytime: 88°F - Nighttime: 72°F
image
Fall (September to November)

Autumn offers milder weather and fewer crowds, creating a peaceful environment for your stay. This is often considered the best time for booking villas with more availability and competitive prices.

Average Temperature Daytime: 82°F - Nighttime: 65°F

Weekly Weather Forecast for Windward

How to Book Your Windward Villa

What's our booking process?

Our platform allows you to browse a curated selection of villa. 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 Villa in Windward Area

Common Villa Amenities

What amenities can you expect?

Our Villa 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 a private outdoor swimming pool to relax and unwind in the warm Florida sun.
  • Take advantage of spacious lanai or screened-in porches perfect for outdoor dining and entertaining.
  • Benefit from direct access to scenic patios or decks for enjoying the fresh air and beautiful views.
  • Make use of well-maintained outdoor grilling areas to prepare delicious meals al fresco.
  • Relax in lush gardens or landscaped yards that add charm and privacy to your stay.
  • Utilize communal outdoor spaces, such as shared pools or recreational areas, for social activities.
  • Explore nearby walking or biking paths that showcase the natural beauty of this destination.

Top Attractions Around Windward

What attractions are nearby?

In this charming region, you'll find plenty of nearby activities to enjoy, from exploring serene beaches and nature preserves to engaging in water sports and fishing excursions that highlight the area's coastal beauty, making it an ideal destination for those seeking relaxation and adventure alike.

image
image

Family Activities

  • Capstan Park: Enjoy outdoor family adventures at this scenic park featuring playgrounds, picnic areas, and walking trails perfect for exploring the natural beauty of the region.
  • Placida Marina: Experience a fun day on the water by renting boats or taking guided tours that allow your family to discover the stunning coastal waterways surrounding this destination.
  • Stump Pass Beach State Park: Relax on pristine sandy beaches, collect shells, or have a peaceful picnic while appreciating the breathtaking Gulf views here in this coastal haven.
  • Englewood Beach: Spend quality family time strolling along the shoreline, swimming, or watching vibrant sunsets at this popular spot known for its welcoming atmosphere.
image

Adult Activities

  • Deep-Sea Fishing: Experience the thrill of deep-sea fishing excursions available in this coastal region, perfect for adults seeking outdoor adventure and relaxation on the water.
  • Golfing: Play a round of golf at nearby courses renowned for scenic views and challenging fairways, ideal for leisure and sports enthusiasts alike.
  • Sailing and Boating: Enjoy exploring the waters by sailing or renting a boat, offering a tranquil way to take in the area's natural beauty and marine life.
  • Paddleboarding and Kayaking: Engage in paddleboarding or kayaking activities along calm waters, providing both exercise and serene scenery for an enjoyable day outdoors.

Windward Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Secure your preferred villa in Windward, Placida early to ensure availability during peak seasons and holidays.
  • Explore Local Beaches: Take advantage of the proximity to beautiful beaches in this region for relaxing days under the sun.
  • Discover Waterfront Activities: Engage in boating, fishing, or kayaking to fully enjoy the scenic waterways surrounding your stay.
  • Experience Seasonal Events: Check the local calendar for seasonal festivals and events that showcase the area's vibrant community vibe.

Transportation Options

  • Personal Vehicles: Renting or using your own car is a convenient way to explore the area, providing flexibility to visit nearby beaches and attractions.
  • Shuttle Services: Local shuttle options operate frequently, offering an easy, reliable means of transportation between popular destinations and your villa.
  • Taxi and Rideshare: Taxis and rideshare services like Uber or Lyft are readily available for quick trips around this destination, ensuring comfort and convenience.
  • Boat Rentals: Given the region’s proximity to water, renting a boat can offer unique access to nearby waterways and secluded spots not reachable by land.

Local Customs Options

  • Respect for Marine Environment: Locals here often observe eco-friendly practices, especially when enjoying the region's stunning coastal waters and beaches.
  • Seafood Dining Etiquette: When dining in this area, it’s customary to appreciate fresh local seafood, which is a staple of the regional cuisine.
  • Respect for Waterfront Properties: Modest behavior around private water-based properties and docks shows appreciation for the area's scenic surroundings.
  • Limited Noise Levels: Maintaining quiet hours, particularly during the evening, aligns with the relaxed atmosphere that visitors cherish in this destination.

Frequently Asked Questions About Windward Rental Villas

1. What are the top Villas 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 Villas in Windward:

2. How many Villas are available in Windward?

Currently, the total number of properties listed by RBO in 2026 is over 145 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Windward. 

3. What is the cancellation policy for villas in this destination?

The cancellation policy varies depending on the specific villa listing. It is recommended to review the individual property's terms and conditions on the listing page or contact the owner directly for detailed information.

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

Additional fees such as cleaning charges, service fees, or security deposits may apply based on the property. Please refer to the listing details or reach out to the host for a complete fee breakdown.

5. How do I confirm my reservation and what is required at check-in?

Reservation confirmation depends on the property's booking process. Typically, you'll receive instructions from the property owner after booking, including check-in procedures and any identification or deposit requirements.

6. Is early check-in or late check-out available at these villas?

Special arrangements like early check-in or late check-out are subject to availability and must be coordinated with the host in advance. It's best to inquire directly during the booking process.

7. What amenities and accommodations can I expect at villas in this area?

Amenities vary by property but often include features such as fully equipped kitchens, private pools, and outdoor living spaces. For specific amenities, please review the villa's listing or contact the owner for further details.

More Rentals You May Like Near Windward

More Top-Rated Villa in Windward Area