Discover Your Perfect Windsor Beach Rentals by Owner

Windsor Beach Rentals by Owner

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10.0 (1 Review)
Resort
Rosewood Bermuda
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Windsor Beach Area

Why Choose Rent By Owner for your Windsor Beach vacation rental?

What makes our Rentals by Owner 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 Windsor Beach

When should you plan your Rentals by Owner stay?

Choosing the optimal time to visit here ensures you experience the region's charm at its best, whether you're seeking warm weather or quieter off-peak moments to enjoy your rental by owner in Windsor Beach, St. George's, Bermuda.

Peak Season Highlights

spring
Spring (April to June)

During this period, the area experiences warm weather ideal for enjoying outdoor activities and exploring the scenic coastal views.

Average Temperature Daytime: around 75°F to 80°F - Nighttime: about 65°F
autumn
Autumn (September to November)

This time of year offers pleasant temperatures and fewer crowds, making it perfect for tranquil stays by the water.

Average Temperature Daytime: approximately 75°F - Nighttime: roughly 67°F

Off-Season Highlights

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Summer (July to August)

While summer is popular here, it can be quite busy; booking early ensures you secure a comfortable rental during the peak months.

Average Temperature Daytime: around 85°F to 88°F - Nighttime: about 75°F
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Winter (December to February)

Off-peak winter visits offer a more peaceful experience, with mild temperatures suitable for relaxing escapes without the crowds.

Average Temperature Daytime: roughly 65°F - Nighttime: about 58°F

Weekly Weather Forecast for Windsor Beach

How to Book Your Windsor Beach vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Windsor Beach

More Top-Rated Rentals by Owner in Windsor Beach Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 dining areas perfect for meals with a view of the water.
  • Relax on private patios or decks that offer scenic vistas of the surrounding landscape.
  • Make the most of your stay with access to lush, well-maintained gardens or green spaces.
  • Take advantage of outdoor grilling stations ideal for cookouts in the region’s pleasant climate.
  • Benefit from direct access to beaches or waterfront areas for swimming and sunbathing.
  • Utilize dedicated outdoor lounging areas designed for relaxation and socializing under the Bermuda sun.
  • Experience the convenience of outdoor showers for rinsing off after a day at the nearby shoreline.

Top Attractions Around Windsor Beach

What attractions are nearby?

Located nearby, you can enjoy a variety of outdoor activities and cultural experiences that showcase the unique charm of this destination, making your stay here both relaxing and memorable.

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Family Activities

  • Snorkeling at the Bermuda Underwater Exploration Institute: Discover the vibrant marine life in the clear waters just off the coast, perfect for family adventures in this region.
  • Beach Day at Warwick Long Bay: Enjoy sunbathing, swimming, and sandcastle building with your loved ones along this scenic shoreline in the area.
  • Exploring St. George’s Historic Town: Take a family stroll through the UNESCO World Heritage Site, where you can learn about the region's rich history and culture together.
  • Visit to the Bermuda Aquarium, Museum and Zoo: Engage young explorers with exhibits showcasing local wildlife and interactive displays in this family-friendly attraction nearby.
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Adult Activities

  • Sightseeing Cruises: Embark on a relaxing cruise to explore the scenic coastline and vibrant marine life in the waters surrounding here.
  • Snorkeling and Diving: Discover the crystal-clear waters teeming with colorful fish and coral formations, offering an unforgettable aquatic adventure close to your rental.
  • Beachside Dining: Savor delicious local cuisine at seaside restaurants where you can enjoy stunning views over the bay after a day of exploration.
  • Historical Tours: Visit nearby historical sites and landmarks that showcase the rich heritage of this destination’s region, providing cultural insights just minutes from your accommodation.

Windsor Beach Travel Tips

How Can You Make the Most of Your Stay?

  • Plan ahead for local experiences: Take time to explore nearby eateries and shops to fully immerse yourself in the authentic charm of this destination.
  • Choose accommodations with picturesque views: Select rental properties that offer scenic vistas of the area to enhance your overall stay and create lasting memories.
  • Make use of the region’s outdoor opportunities: Prioritize rentals close to beaches or parks to maximize your outdoor adventures and relaxation.
  • Utilize local transportation options: Opt for conveniently located rentals that allow easy access to key attractions, making your stay more convenient and enjoyable.

Transportation Options

  • Local Bus Service: You can easily rely on the regional bus network for convenient transportation around Windsor Beach and the surrounding area, offering an affordable way to explore the region.
  • Taxis and Rideshare Services: Taxi cabs and rideshare options are readily available here, providing flexible and quick transfers between your rental and local attractions.
  • Car Rentals: Renting a car gives you the freedom to explore beyond Windsor Beach at your own pace, with numerous rental agencies conveniently located nearby.
  • Bermuda Water Taxis: For scenic travel along the coast, water taxis operate in the area, offering a unique and picturesque way to traverse this destination's waterfront.

Local Customs Options

  • Respect for Local Protocols: You’ll find that observing local customs, such as greeting with a friendly nod or handshake, helps you connect authentically with residents here in Windsor Beach, St. George's.
  • Environmental Awareness: Visitors are encouraged to follow eco-friendly practices, including proper waste disposal and respecting protected natural areas along the coastline.
  • Cultural Appreciation: Engaging respectfully with Bermudian traditions, like participating in local festivities or learning about maritime history, enriches your experience in this vibrant part of the region.
  • Community Engagement: Supporting small businesses and local artisans not only enhances your stay but also fosters meaningful connections within the area.

Frequently Asked Questions About Windsor Beach Rentals by Owner

1. What are the top vacation rentals in Windsor Beach?

There are a lot of options in Windsor Beach. If you plan on staying in the Windsor Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor Beach:

2. How many Rentbyowner vacation rentals are available in Windsor Beach?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 52 in the Windsor Beach 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 Windsor Beach. 

3. What is the cancellation policy for rentals by owner in Windsor Beach, St. George's?

The cancellation policy varies depending on the individual host and listing. To ensure you understand the specific terms, please review the cancellation details provided in the listing or contact the owner directly before booking.

4. How do I contact the property owner to ask about amenities and house rules in this region?

You can reach out to the property owner through the messaging feature on the Rent By Owner platform. This allows you to clarify any questions regarding amenities, house rules, and other relevant details before confirming your reservation.

5. Are there any additional fees I should be aware of when booking a rental by owner here?

Additional fees such as cleaning charges, service fees, or local taxes are typically listed during the booking process. It’s advisable to review the total price breakdown on the listing and contact the owner if you have specific questions about extra charges.

6. What safety measures are in place for rentals by owner in this destination?

Safety features and protocols vary from one property to another. You should review the listing details for information on security measures and reach out to the owner for any specific concerns or questions related to safety during your stay.

7. Is Wi-Fi included in rentals by owner in this area, and how reliable is it?

Most listings include Wi-Fi access, but connection quality and reliability can differ. Check the property description for Wi-Fi details and contact the owner if you need confirmation or have specific internet requirements.

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