Windward Oceanfront Vacation Rentals
Condo
10.0(168 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $438/Night
7 Nights - US $3,066
Villa
10.0(5 Reviews)
3 Bedrooms
3 Baths
6 Guests
2002.09 ft²
Pool- Ocean View
- Balcony/Terrace
View
US $186/Night
7 Nights - US $1,302
Cottage
10.0(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $298/Night
7 Nights - US $2,086
Condo
10.0(72 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $578/Night
7 Nights - US $4,048
Villa
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1345.49 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $235/Night
7 Nights - US $1,645
Condo
10.0(65 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $292/Night
7 Nights - US $2,045
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1636.11 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $275/Night
7 Nights - US $1,923
Condo
10.0(42 Reviews)
2 Bedrooms
2 Baths
4 Guests
946 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $378/Night
7 Nights - US $2,646
Apartment
10.0(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
Private Beach- Oceanfront
- Ocean View
- View
US $116/Night
7 Nights - US $814
House
10.0(39 Reviews)
3 Bedrooms
2 Baths
8 Guests
1812 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $378/Night
7 Nights - US $2,646
House
10.0(1 Review)
3 Bedrooms
2 Baths
9 Guests
2098.96 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $434/Night
7 Nights - US $3,039
Cottage
10.0(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $353/Night
7 Nights - US $2,472
Why Choose Rent By Owner for your Windward Oceanfront Vacation Rentals?
What makes our Oceanfront 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 Oceanfront Vacation Rentals
Where are the best neighborhoods to stay in Windward?
Discover the charming neighborhoods within Windward, Placida, Florida, where you can enjoy tranquil surroundings and stunning waterfront views. Staying in this area offers easy access to beautiful beaches and serene coastal landscapes, perfect for relaxing oceanfront rentals. Whether you're seeking a peaceful retreat or an adventurous getaway, the neighborhood's inviting atmosphere makes it an ideal choice for your next stay.
Cape Haze
This area offers a peaceful retreat with scenic views and a tranquil atmosphere, making it an ideal choice for those seeking relaxing oceanfront rentals. Here, you can enjoy the natural beauty of the region while staying close to premium waterfront accommodations.
View 61+ Rentals in Cape HazeBest Times to Visit Windward
When should you plan your Oceanfront Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, as certain seasons in the region offer ideal weather for enjoying the stunning oceanfront rentals and relaxing by the water's edge.
Peak Season Highlights
Winter (December to February)
During the winter months, you can enjoy milder temperatures and less humidity, making it an ideal time to experience this destination's tranquil coastal environment.
Average Temperature Daytime: 70°F to 75°F - Nighttime: 55°F to 60°F
Spring (March to May)
Spring offers pleasant weather with warm days and blooming landscapes, creating a perfect setting for enjoying oceanfront rentals in this region.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Off-Season Highlights
Summer (June to August)
The summer season is characterized by higher temperatures and increased humidity, attracting visitors looking to indulge in water activities and beach relaxation.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 70°F to 75°F
Fall (September to November)
Fall brings cooler air and less crowded beaches, offering a peaceful retreat while still enjoying warm ocean breezes in this coastal area.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 68°F
Weekly Weather Forecast for Windward
How to Book Your Windward Oceanfront Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of oceanfront 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
Common Oceanfront Vacation Rentals Amenities
What amenities can you expect?
Our Oceanfront 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 private outdoor patios or balconies with scenic views of the Gulf of Mexico.
- Take advantage of community pools and hot tubs often available in the area’s vacation complexes.
- Relax on pristine beaches just steps from your rental, perfect for sunbathing and shell collecting.
- Utilize well-maintained outdoor grilling stations for family cookouts with oceanfront settings.
- Explore nearby walking trails and nature paths that wind through the region’s natural beauty.
- Access outdoor recreational equipment such as kayaks, paddleboards, or bicycles offered by rentals.
- Make use of beautifully landscaped gardens and outdoor lounge areas designed for relaxation.
Top Attractions Around Windward
What attractions are nearby?
Enjoy a variety of water-based activities and scenic nature excursions just minutes from your oceanfront rental in Windward, where you can explore the nearby waterways, relax on pristine beaches, or indulge in memorable fishing experiences that showcase the region's natural beauty and coastal charm.
Family Activities
- Pelican Landing Preserve Explore this scenic nature preserve for family-friendly trails and opportunities to observe local wildlife in a peaceful setting.
- Placida Marina Enjoy a boat rental or guided tour, perfect for families looking to experience the area’s beautiful waters and marine life firsthand.
- Local Beaches Relax and play on sandy shores with shallow waters ideal for children, making it an excellent spot for family picnics and beach activities.
- Fishing Charters Embark on a family fishing adventure suitable for all ages, offering memorable experiences amid the region’s rich aquatic environment.
Adult Activities
- Deep-Sea Fishing: Experience the thrill of a deep-sea fishing adventure in this area, renowned for its abundant marine life and expert-guided excursions.
- Sunset Cruises: Enjoy breathtaking sunsets over the Gulf of Mexico on a relaxing cruise that showcases the area's stunning coastal scenery.
- Kayaking & Paddleboarding: Explore calm waters and scenic shorelines by renting a kayak or paddleboard, perfect for both beginners and seasoned adventurers.
- Wildlife Watching: Discover local wildlife, including dolphins and seabirds, through guided tours or self-led explorations along the pristine coastlines.
Windward Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead Secure your stay early to enjoy a wide selection of oceanfront rentals and ensure you get the best views and amenities available in this area.
- Explore Local Beaches Take advantage of the region’s pristine beaches for relaxing days on the sand and engaging in water activities that showcase the natural beauty here.
- Discover Nearby Dining Sample local cuisine at nearby restaurants to immerse yourself in the regional flavors unique to this destination.
- Utilize Water Transportation Consider boat rentals or tours to explore the surrounding waters, providing a different perspective of this coastal region and making the most of your stay.
Transportation Options
- Rental Car Services: Local rental car companies offer convenient options for exploring the area and accessing your oceanfront rentals with ease.
- Public Transportation: Buses and shuttles provide affordable and reliable transportation throughout this destination, making it simple to get around without a vehicle.
- Taxi and Ride-Sharing: Taxis and ride-sharing services like Uber and Lyft are readily available here, offering flexible transport options for quick trips or last-minute needs.
- Private Boat Charters: Given the region’s coastal setting, private boat charters are popular, providing unique ways to enjoy the water and reach your seaside accommodations.
Local Customs Options
- Greeting Customs: Locals in the region often exchange warm greetings such as "Hello" or "Good morning," reflecting the friendly and welcoming nature of this coastal community.
- Respect for Nature: Preserving the pristine environment is a priority here, with residents typically practicing eco-friendly habits like proper disposal of waste and respecting wildlife habitats.
- Community Celebrations: The area hosts traditional festivals and local events that celebrate maritime heritage and regional history, offering visitors a glimpse into its cultural roots.
- Dress Code: Casual and beach-appropriate attire is customary when visiting shared public spaces, emphasizing comfort and relaxation during your stay at oceanfront rentals here.
Frequently Asked Questions About Windward Oceanfront Rentals
1. What are the top Oceanfront 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 Oceanfront Rentals in Windward:
- Ibis Landing Beach House.Directly on the Beach! Don Pedro/Palm Island
- Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
- Light and airy, beautifully appointed 3 bed, 3 bath home with sunny pool & spa.
- Seeing is Believing! Incredible Boca Vista Harbor Waterfront Condo!
- Cloud 9 on LGI Beach! No Roads. No Cars. Just Island Life w/Beach to Bay Views.
- Island Breeze
- Not the average vacation home! Saltwater Pool & Spa electric heat incl. in rate
- Modern holiday villa overlooking the lake and the golf course
- Enchanted Private Island Oasis Steps To Beach, Tropical Yard & Charm Filled Home
- Island Beach Barn - charming vacation house with bay/dock and beach access
2. How many Oceanfront Rentals are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 728 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in Windward.
3. What is the cancellation policy for oceanfront rentals in this area?
The cancellation policies vary by listing, so it’s best to review the specific terms outlined in the property details before booking. For detailed information, contact the property owner directly to understand any applicable fees or deadlines.
4. Are there any additional fees I should be aware of when booking an oceanfront rental here?
Additional fees such as cleaning, service charges, or security deposits may apply depending on the property. Please refer to the listing details or speak with the host for a complete breakdown of all costs involved.
5. What amenities are typically included in oceanfront rentals in this destination?
Most properties offer essential amenities like Wi-Fi, fully equipped kitchens, and outdoor spaces. Specific features such as waterfront access, private decks, or pools are listed individually, so check the property description for comprehensive details.
6. How do I confirm the availability of an oceanfront rental during my preferred dates?
Availability depends on current bookings, which you can verify directly through the listing. If the dates are not available online, consider reaching out to the owner for potential flexibility or alternative options.
7. What steps should I take to ensure a smooth check-in process at my chosen oceanfront rental?
Details about check-in procedures are provided in the listing, including key collection and arrival instructions. It’s advisable to contact the property owner beforehand to clarify any questions and confirm your arrival plans.
More Rentals You May Like Near Windward
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
2034.38 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $352/Night
7 Nights - US $2,464
House
10.0(32 Reviews)
3 Bedrooms
2 Baths
8 Guests
1600 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
US $208/Night
7 Nights - US $1,455
House
10.0(30 Reviews)
2 Bedrooms
2 Baths
6 Guests
1344 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $484/Night
7 Nights - US $3,388
House
10.0(28 Reviews)
2 Bedrooms
2 Baths
5 Guests
946 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $306/Night
7 Nights - US $2,144
Condo
10.0(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Pool
US $317/Night
7 Nights - US $2,217
House
10.0(20 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $124/Night
7 Nights - US $870
House
10.0(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $361/Night
7 Nights - US $2,527
House
10.0(18 Reviews)
2 Bedrooms
2 Baths
8 Guests
1460 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $162/Night
7 Nights - US $1,137
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $520/Night
7 Nights - US $3,639
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $355/Night
7 Nights - US $2,486
Condo
10.0(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
1111 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $470/Night
7 Nights - US $3,291
Villa
10.0(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $453/Night
7 Nights - US $3,173
