1. Jamaica
  2. Trelawny
  3. Windsor
  4. Rentals by Owner

Discover Your Perfect Windsor Rentals by Owner

Windsor Rentals by Owner

10.0 (4 Reviews)
House
Deja Blu!!
  • Air Conditioner
  • Parking
  • Pool
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More Top-Rated Rentals by Owner in Windsor Area

Why Choose Rent By Owner for your Windsor 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

When should you plan your Rentals by Owner stay?

Timing your visit to this destination can greatly enhance your experience, so consider planning your vacation during the region’s peak seasons when the weather is ideal and local events create a vibrant atmosphere for your stay.

Peak Season Highlights

spring
December to April

This peak season in Windsor, Trelawny offers ideal weather conditions, making it perfect for outdoor activities and exploring the region's natural beauty.

Average Temperature Daytime: 28°C - Nighttime: 20°C
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July to August

During these months, the area experiences warm weather conducive to relaxing on the beaches or enjoying local events, attracting many visitors seeking a vibrant Caribbean atmosphere.

Average Temperature Daytime: 30°C - Nighttime: 22°C

Off-Season Highlights

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May to June

These months typically see fewer travelers, offering a peaceful retreat with pleasant weather and fewer crowds to enjoy your stay by the coast or in the countryside.

Average Temperature Daytime: 29°C - Nighttime: 21°C
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September to November

As the region transitions into the off-peak period, you can benefit from more affordable rentals and less busy attractions, making it an ideal time for a tranquil vacation experience.

Average Temperature Daytime: 28°C - Nighttime: 20°C

Weekly Weather Forecast for Windsor

How to Book Your Windsor 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

More Top-Rated Rentals by Owner in Windsor 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 a private outdoor swimming pool to relax in the warm Caribbean sun.
  • Benefit from lush gardens and landscaped outdoor spaces that add charm to your stay.
  • Take advantage of spacious patios or verandas for outdoor dining and entertainment.
  • Make the most of outdoor grilling areas to prepare delicious meals al fresco.
  • Experience the region’s natural beauty with available outdoor seating areas for soaking in the scenery.
  • Utilize outdoor recreational facilities such as tennis courts or sports areas often found nearby.
  • Relax under shaded gazebos or pergolas designed for lounging in the fresh air.

Top Attractions Around Windsor

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of activities such as exploring beautiful beaches or engaging in local cultural experiences, making your stay in Windsor, Trelawny a memorable and enriching escape.

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Family Activities

  • Green Grotto Caves: Explore this fascinating limestone cavern system just minutes from your accommodation, offering an exciting adventure for the whole family in the region.
  • Chukka Caribbean Adventures: Experience thrilling outdoor activities like zip-lining and river tubing that showcase the natural beauty of the area while providing fun-filled moments for all ages.
  • Windsor Beach: Relax on the sandy shores of Windsor Beach, where you can enjoy swimming, picnicking, and soaking up the sun in a safe and scenic environment.
  • Jamaica Hummingbird Sanctuary: Discover a variety of colorful tropical birds at this nearby sanctuary, offering an educational and engaging experience for young wildlife enthusiasts.
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Adult Activities

  • Sailing and Snorkeling Adventures: Experience the crystal-clear waters by joining a sailing tour or snorkeling excursion while visiting the area, allowing you to explore vibrant marine life firsthand.
  • Golfing at Local Courses: Tee off at nearby golf courses that offer scenic views and challenging fairways, making for a relaxing yet engaging day in this tropical region.
  • Visit to Trelawny Parish Museum: Discover the rich history and culture of the area through exhibits and artifacts at the local museum, providing a meaningful cultural experience.
  • Relaxing at Secluded Beaches: Unwind on quiet beaches accessible from here, perfect for sunbathing, swimming, or enjoying a peaceful day away from crowds.

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Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Arrive Prepared: Familiarize yourself with the local weather and culture to make your stay in Windsor more comfortable and culturally enriching.
  • Engage with the Community: Support local businesses and interact with residents to fully experience the authentic atmosphere of this Jamaican destination.
  • Plan Your Activities: Schedule outdoor adventures and relaxation time wisely to maximize your enjoyment while respecting the area’s natural beauty.
  • Choose a Well-Reviewed Rental: Opt for a trusted owner-managed accommodation through Rent By Owner to ensure a seamless and reliable stay in Trelawny's charming region.

Transportation Options

  • Local Taxis: Reliable and convenient for getting around the area, with drivers familiar with Windsor's best routes and attractions.
  • Private Car Rentals: Perfect for exploring this part of Jamaica at your own pace, offering flexible schedules and personalized trips.
  • Public Buses: An affordable transportation option that connects you to key destinations within the region, ideal for budget-conscious travelers.
  • Shuttle Services: Pre-arranged shuttles provide seamless transfers from nearby airports or popular points of interest in the area.

Local Customs Options

  • Greeting Etiquette: When visiting here, it is customary to greet locals with a warm smile and a friendly "hello" or "good morning," reflecting the area's welcoming spirit.
  • Respect for Local Religion: Visitors often observe respectful behavior in places of worship and during religious festivities, which are significant cultural customs in this region.
  • Traditional Dress: During special events or celebrations, dressing modestly and incorporating traditional attire shows appreciation for the area's customs and can enrich your experience.
  • When enjoying local eateries, it’s polite to try traditional dishes and show gratitude through compliments, supporting the area's culinary heritage.

Frequently Asked Questions About Windsor Rentals by Owner

1. What are the top vacation rentals in Windsor?

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 427 in the Windsor 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. 

3. What is the cancellation policy for a rental by owner in Windsor, Trelawny?

Cancellation policies vary by listing. You should review the specific terms outlined on the rental's page or contact the owner directly for detailed information about cancellations and possible fees.

4. How do I secure my booking at a rental property in this region?

Booking procedures are outlined on the listing. Typically, securing your reservation involves completing the online booking process and confirming payment details. For additional assistance, reaching out to the owner is recommended.

5. Are there any specific check-in and check-out times I should be aware of?

Check-in and check-out times are specified in each listing. To ensure a smooth arrival and departure, please refer to these details or communicate directly with the property owner for any special arrangements.

6. What amenities are included in rentals by owner in this destination?

Amenities can differ from one property to another. The listing will detail what is available, such as Wi-Fi, kitchen facilities, or air conditioning. If you have specific needs, contacting the owner beforehand is advisable.

7. How can I get more details about the property before booking?

You can review the full property description, photos, and guest reviews on the listing page. For further questions or clarifications, reaching out directly to the owner ensures you have all the necessary information.

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More Top-Rated Rentals by Owner in Windsor Area