Discover Your Perfect Windsor Beach Vacation Homes

Best Vacation Homes in Windsor Beach

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10.0 (1 Review)
Resort
Rosewood Bermuda
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability

Why Choose Rent By Owner for your Windsor Beach 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.

Best Times to Visit Windsor Beach

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as seasonal weather and local events in Windsor Beach, St. George's, Bermuda, significantly influence the enjoyment of your vacation rental stay.

Peak Season Highlights

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April to June

During the spring months, this destination experiences warm weather and lively atmosphere, making it ideal for exploring the scenic beaches and enjoying outdoor activities.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 65°F to 75°F
spring
December to March

Winter offers a mild climate with less crowding, perfect for those seeking a peaceful retreat while still enjoying comfortable daytime temperatures in the region.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 60°F to 65°F

Off-Season Highlights

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July to September

Summertime here brings high temperatures and increased tourism, but you can find excellent vacation rentals if you prefer fewer crowds during this period.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 75°F to 80°F
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October to November

Autumn sees a gradual decrease in visitors, offering more tranquility and competitive rates for your stay on this island destination.

Average Temperature Daytime: 78°F to 82°F - Nighttime: 68°F to 72°F

Weekly Weather Forecast for Windsor Beach

How to Book Your Windsor Beach 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 Windsor Beach

More Top-Rated Vacation Rentals in Windsor Beach 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 private outdoor dining areas perfect for soaking up the sunshine while overlooking the scenic surroundings.
  • Capitalize on access to well-maintained swimming pools and sun loungers, ideal for relaxing in the warm Bermuda weather.
  • Make use of shaded patios or verandas that provide a comfortable spot to unwind after a day exploring the area.
  • Benefit from outdoor BBQ grills, great for hosting gatherings and savoring local flavors under the Bermuda sky.
  • Take advantage of lush gardens or landscaped yards that enhance your outdoor living experience here.
  • Utilize nearby beachfront access or private beaches for swimming, sunbathing, and water activities along the coast.
  • Access outdoor recreational facilities such as tennis courts or playgrounds, which are common amenities at many local properties.

Top Attractions Around Windsor Beach

What attractions are nearby?

Nearby, you can explore a variety of outdoor activities and scenic spots that make this destination perfect for relaxing and adventure, all within easy reach of your accommodations in Windsor Beach, St. George's, Bermuda.

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Family Activities

  • Snorkeling at Windsor Beach: Explore the vibrant marine life just off the shoreline, making it a perfect family activity in this scenic Bermuda destination.
  • Relaxing on Windsor Beach: Spend quality time together soaking up the sun and enjoying the soft sands along this popular beach area.
  • Kayaking Adventures: Rent a kayak and paddle along the calm waters, offering a fun way for families to explore the region’s stunning coastal scenery.
  • Beachside Picnics: Pack a picnic and enjoy a leisurely meal with ocean views right by Windsor Beach, ideal for family bonding moments.
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Adult Activities

  • Snorkeling Adventures: Explore the vibrant marine life just off the coast, making it a must-do activity for those seeking underwater exploration in this destination.
  • Paddleboarding Experiences: Enjoy a relaxing day on calm waters by renting a paddleboard and taking in scenic views around the area.
  • Beachside Yoga: Participate in rejuvenating yoga sessions directly on the sandy shores, ideal for unwinding amidst Nature's tranquility.
  • Fishing Excursions: Embark on guided fishing trips that offer the chance to catch local species while soaking up the serene surroundings of this region.

Windsor Beach Travel Tips

How Can You Make the Most of Your Stay?

  • Arrive Early and Plan Ahead: Making the most of your stay means arriving early to enjoy the serene beaches and planning activities around the area's beautiful natural surroundings.
  • Explore Local Cuisine: Take time to sample authentic Bermudian dishes at nearby eateries to truly immerse yourself in the region's culinary culture.
  • Utilize Water Activities: Engage in water-based adventures, such as snorkeling or kayaking, to experience the vibrant marine life just offshore here.
  • Choose a Prime Location: Selecting a vacation rental close to Windsor Beach ensures easy access to the beach and local amenities, enhancing your overall relaxation and convenience.

Transportation Options

  • Public Ferry Service: You can easily access the region's scenic views and neighboring islands via the reliable public ferry network, which offers a convenient way to explore here without the need for a car.
  • Rental Cars: Renting a car provides you with the flexibility to explore the area at your own pace and visit nearby attractions comfortably from your Windsor Beach accommodation.
  • Taxis and Rideshare Services: Taxis and rideshare options are readily available, offering a quick and hassle-free way to navigate here without the worries of parking or driving yourself.
  • Bermuda Airport Transfers: Dedicated transfer services from Bermuda Airport ensure seamless transportation directly to your vacation rental in this destination, making arrivals and departures smooth and stress-free.

Local Customs Options

  • Respect for the Sea: Locals in this region have a deep appreciation for maritime traditions, often observing customs that honor the ocean’s role in their community.
  • Greeting Etiquette: When you visit here, it’s customary to exchange warm greetings with residents, reflecting the area's friendly and welcoming spirit.
  • Cultural Celebrations: Participating in local festivals offers a glimpse into the area's vibrant heritage, showcasing traditional music, dance, and costumes.
  • Environmental Respect: Visitors and locals alike prioritize preserving the natural beauty of the region, engaging in environmentally conscious practices during their stay.

Frequently Asked Questions About Windsor Beach?

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 64 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 vacation rentals in Windsor Beach, St. George's, Bermuda?

Cancellation policies vary depending on the property owner and specific listing. You should review the cancellation terms detailed in the rental listing or contact the host directly to understand the refund window and any applicable fees.

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

Additional fees such as cleaning charges, service fees, or security deposits are often listed with the property details. To avoid surprises, check the listing thoroughly or reach out to the host for clarification before completing your booking.

5. How do I ensure my stay complies with local regulations in this region?

Each property listing may include information about local rules and regulations. Contact the property owner if you need further guidance to ensure your stay aligns with the area's requirements and enjoy a trouble-free visit.

6. Is there a minimum stay requirement for vacation rentals in Windsor Beach, St. George's, Bermuda?

Minimum stay requirements can vary depending on the property. The specific details are provided within each listing, so review these or communicate directly with the host to confirm your booking duration.

7. What amenities are typically included in vacation rentals here?

Most listings feature essential amenities such as Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces. For a complete list of amenities, refer to the detailed property description or contact the owner directly to ensure it meets your needs.

Best Vacation Homes in Windsor Beach

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9.4 (33 Reviews)
Hotel
The Loren at Pink Beach
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
10.0 (5 Reviews)
Cottage
Cozy Gombey Cottage
  • Air Conditioner
  • TV
  • Balcony/Terrace
View Availability