Best Vacation Homes in Windsor
- Air Conditioner
- Parking
- TV
- 592 ftยฒ Apartment
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pool
- TV
- Air Conditioner
- Parking
- TV
Windsor Luxury Rentals
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pool
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
Windsor Pet Friendly Vacation Rentals
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Windsor Large Vacation Homes
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
Why Choose Rent By Owner for your Windsor Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Windsor
When should you plan your Vacation Rentals stay?
Choosing the right time to visit ensures you enjoy the best weather and local experiences when exploring Windsor in Trelawny, Jamaica, making it an ideal destination for your vacation rental plans.
Peak Season Highlights
December to April
During the dry season, you'll experience warm daytime temperatures ideal for outdoor activities and exploring the region's natural beauty. This is when the area sees an influx of visitors seeking sun-soaked days and pleasant evenings.
July to August
The summer months bring lively energy and vibrant local events, attracting travelers looking to enjoy the warm weather and lush scenery. It's a popular time for beach visits and outdoor adventures in this destination.
Off-Season Highlights
May to June
As the rainy season approaches, you might find fewer crowds and more affordable rates, making it a great time to enjoy a peaceful stay here. The region experiences occasional showers but remains warm and inviting.
September to November
During this period, the area sees less tourist traffic, offering a more relaxed atmosphere. While there may be some rainfall, the warm climate still allows for outdoor relaxation and exploration.
Weekly Weather Forecast for Windsor
How to Book Your Windsor Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Windsor
Common Vacation Rentals Amenities
What amenities can you expect?
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 swimming pool for relaxing or entertaining outdoors.
- Make the most of lush gardens and landscaped yards that enhance the outdoor ambiance.
- Use outdoor dining areas perfect for savoring local cuisine under the sun or stars.
- Take advantage of spacious patios or verandas designed for lounging and socializing.
- Access outdoor grilling facilities to experience authentic Jamaican barbecues.
- Benefit from shaded lounge areas to unwind comfortably in the warm tropical climate.
- Explore nearby walking paths or gardens that showcase the natural beauty of the region.
Top Attractions Around Windsor
What attractions are nearby?
In this vibrant region, you can enjoy a variety of outdoor activities such as exploring beautiful beaches, engaging in water sports, or discovering lush parks and scenic trails nearby your vacation rentals.
Family Activities
- Rose Hall Great House Tour: Discover the regionโs rich history by exploring this historic plantation estate, offering engaging guided tours for families interested in local heritage.
- Goat Island Adventure: Experience a fun-filled day on this nearby island with opportunities for snorkeling, swimming, and relaxing in natural surroundings suitable for all ages.
- Chukka Caribbean Adventures: Enjoy an array of outdoor activities like horse riding and river tubing designed to create memorable family adventures in the areaโs scenic landscapes.
- Dolphin Cove Jamaica: Interact with dolphins and marine life at this popular attraction, providing an educational and entertaining experience for children and adults alike.
Adult Activities
- Visit the Trelawny Parish Church: Explore this historic site to appreciate the region's architectural heritage and local history.
- Enjoy the Luminous Lagoon: Experience a captivating night-time boat tour where the waters shimmer with natural bioluminescence, offering a magical adventure just minutes from here.
- Explore the Martha Brae River Rafting: Relax on a traditional bamboo raft while taking in the lush scenery along one of the area's most popular waterways.
- Relax at the local beaches: Unwind on pristine shores that provide the ideal setting for sunbathing, swimming, or simply enjoying the tropical breeze of this destination.
Other Places to Stay in Windsor
Windsor Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Experiences: Research and book authentic local tours and activities in advance to immerse yourself fully without missing out on the regionโs vibrant culture.
- Choose a Prime Location: Select vacation rentals situated near key attractions or scenic spots to maximize your time exploring and enjoying the areaโs natural beauty.
- Utilize Local Transportation Options: Take advantage of available transportation services to easily navigate here and avoid unnecessary delays during your stay.
- Respect the Community and Environment: Engage with the community responsibly and follow eco-friendly practices to help preserve the region's natural charm for future visitors.
Transportation Options
- Taxis and Private Transfers: You can easily arrange for taxis or private transfer services to navigate around the area conveniently and comfortably.
- Car Rentals: Renting a car offers you flexibility to explore the region at your own pace, with several local agencies providing reliable options.
- Public Buses: Public buses serve as an affordable and practical way to travel between nearby towns and attractions within the destination.
- Motorbike Rentals: For a more adventurous experience, motorbike rentals allow you to enjoy scenic rides through the regionโs beautiful landscapes with ease.
Local Customs Options
- Respect for Jamaican Heritage: Youโll find that embracing local customs is key to experiencing the authentic hospitality here, especially in this part of Trelawny.
- Greetings and Courtesies: When visiting, be sure to offer a warm "hello" or "good morning" as locals value friendly and respectful interactions.
- Dress Codes for Cultural Sites: Modest attire is recommended when exploring places of cultural significance in the area to show respect for local traditions.
- Celebration of Jamaica Independence: Participating in or observing local festivities during national holidays offers a genuine glimpse into the regionโs vibrant culture.
Frequently Asked Questions About Windsor?
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:
- Queens Cottage 4-Beachfront Villa - Swimming pool, staff, Newly refurbished!
- Beautiful VILLA SEAGULL in Silver Sands Beach Resort
- 2 bedrooms 2bath home in gated area. 24 hours security.
- Tallawah 7-BEACHFRONT! FAMILIES WELCOME! STAFFED! INFINITY POOL! SECURITY
- MODERN BEACH SIDE VILLA
- Good Hope Coach House, historic cut stone house with modern amenities
- Home sweet home Trewlany Falmouth Jamacia a Paradise
- Simmerdown Villa is a spacious modern 4 bedroom house within a gated community
- 3 Bedroom villa with pool on private gated community
- Hibiscus Place is your home away from home. Entire property is available to you!
How many vacation rentals have private pools in Windsor?
There are 49 vacation rentals with private pools near Windsor. Top-rated RBO homes that have access to a swimming pool include:
Which vacation homes in Windsor are best for families?
If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:
How many Rentbyowner vacation rentals are available in Windsor?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 437 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.โฏ
Windsor Top Rated Vacation Rentals
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Pool
- TV
