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  3. La Mesa
  4. Windsor Hills
  5. Rentals by Owner

Discover Your Perfect Windsor Hills Rentals by Owner

Windsor Hills Rentals by Owner

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10.0 (2 Reviews)
House
The Owl House
  • Air Conditioner
  • Parking
  • Security/Safety
View Availability
More Top-Rated Rentals by Owner in Windsor Hills Area

Why Choose Rent By Owner for your Windsor Hills 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 Hills

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here ensures you make the most of your stay, whether you prefer the vibrant seasons or quieter periods in this welcoming area.

Peak Season Highlights

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Spring (March to May)

During spring, you can enjoy pleasant weather and blooming landscapes in the region, making it an ideal time for exploring rentals in the area.

Average Temperature Daytime: 70-75°F - Nighttime: 50-55°F
summer
Summer (June to August)

The summer months bring warm temperatures and longer daylight hours, perfect for outdoor activities and enjoying your stay here.

Average Temperature Daytime: 85-90°F - Nighttime: 60-65°F

Off-Season Highlights

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Fall (September to November)

In fall, the area experiences cooler temperatures and fewer tourists, providing a more relaxed rental experience here.

Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F
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Winter (December to February)

Winter offers mild weather with lower occupancy rates, making it a quiet period to secure your preferred vacation rental in this destination.

Average Temperature Daytime: 55-60°F - Nighttime: 40-45°F

Weekly Weather Forecast for Windsor Hills

How to Book Your Windsor Hills 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 Hills

More Top-Rated Rentals by Owner in Windsor Hills 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

  • Access to a well-maintained outdoor swimming pool for relaxing and leisure.
  • Beautifully landscaped gardens and outdoor seating areas to enjoy the pleasant climate.
  • Outdoor barbecue grills available for family cookouts and gatherings.
  • Fitness amenities such as tennis courts or walking paths nearby for active pursuits.
  • Children’s play areas to keep younger guests entertained outdoors.
  • Patio or balcony spaces with outdoor furniture to unwind while taking in the local scenery.
  • Parking facilities that include convenient outdoor parking options for guests’ ease of access.

Top Attractions Around Windsor Hills

What attractions are nearby?

Within this inviting area, you can enjoy a variety of nearby activities that showcase the natural beauty and local charm of La Mesa, making your stay here both relaxing and memorable.

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Family Activities

  • Windsor Hills Recreation Center: Enjoy a fun-filled day participating in sports, swimming, and outdoor activities at this well-equipped community facility.
  • La Mesa Centennial Park: Explore scenic walking trails, playgrounds, and picnic areas, making it an ideal spot for family outings in the region.
  • The Toy Store of La Mesa: Discover a wide selection of toys and games, perfect for entertaining children and creating lasting memories during your stay here.
  • San Diego County Fairgrounds: Attend seasonal fairs and events, providing entertainment and engaging activities suitable for all ages in the area.
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Adult Activities

  • Windsor Hills Golf Course: Experience a round of golf on a scenic course nestled within the area, perfect for relaxing and enjoying the sunny California weather.
  • La Mesa Historical Society Museum: Explore local history and culture through engaging exhibits that offer insight into this region’s rich heritage.
  • Biking along the San Diego River Trail: Ride along this picturesque trail that weaves through the region, offering stunning views and a great way to stay active during your visit.
  • Wine tasting at nearby vineyards: Indulge in wine sampling sessions at nearby wineries that highlight the best of the region’s viticulture.

Windsor Hills Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Amenities: Take advantage of nearby shops, restaurants, and parks to immerse yourself in the area's vibrant community during your stay.
  • Plan Excursions Ahead: Research popular destinations within La Mesa to optimize your time and experience the best attractions this region offers.
  • Utilize Vacation Rentals Effectively: Choose a rental by owner that provides thoughtful amenities to enhance your comfort while exploring this desirable destination.
  • Connect with Hosts: Communicate clearly with your host to get insider tips and personalized recommendations for making the most of your visit here.

Transportation Options

  • Personal Vehicle: Renting or using your own car offers flexibility and convenience when exploring the area around Windsor Hills, La Mesa, making it easy to reach local attractions and amenities at your pace.
  • Local Bus Services: The region is served by efficient bus routes that connect Windsor Hills with nearby neighborhoods and public transit hubs, providing a budget-friendly transportation option for visitors.
  • Rideshare Services: Companies like Uber and Lyft operate extensively here, offering quick and reliable transportation options for seamless travel within the region and nearby destinations.
  • Car Rentals: Numerous car rental agencies are available locally, allowing you to select from a variety of vehicles suitable for exploring La Mesa and the surrounding area comfortably and conveniently.

Local Customs Options

  • Respect for Neighborhood Privacy: In this area, it’s customary to maintain a considerate distance and avoid intruding on residents' privacy when exploring Windsor Hills and the surrounding region.
  • Community Hospitality: Locals often greet visitors with warmth and friendliness, reflecting the welcoming spirit that characterizes La Mesa and its nearby neighborhoods.
  • Environmental Awareness: Here, there is a strong emphasis on recycling and conserving resources, making eco-friendly practices an important part of your visit to the region.
  • Cultural Appreciation: Recognizing and respecting the diverse backgrounds of the community enhances your experience in this destination, where inclusivity is highly valued.

Frequently Asked Questions About Windsor Hills Rentals by Owner

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 577 in the Windsor Hills 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 Hills. 

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

Cancellation policies vary by listing. You should review the specific rental's cancellation policy on the listing page or contact the owner directly to understand the terms and any applicable fees.

4. How can I confirm availability and book a rental in this area?

Availability can be checked through the listing calendar on the Rent By Owner website. Once you find a suitable property, you can proceed with the booking process online or reach out to the owner for confirmation.

5. Are there any additional fees or charges for staying in a rental by owner here?

Additional fees such as cleaning, service charges, or security deposits are typically detailed on the listing. Be sure to review the full pricing breakdown before completing your reservation.

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

Most rentals offer amenities like Wi-Fi, parking, kitchen access, and laundry facilities. Specific amenities vary per property, so check the listing details to ensure it meets your needs.

7. How do I communicate with the property owner before booking?

You can contact the owner directly via the messaging system provided on the listing page. This allows you to ask questions about the property, inquire about special requests, or clarify any concerns before booking.

More Rentals You May Like Near Windsor Hills

10.0 (47 Reviews)
House
Travel Writer's Pad
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Windsor Hills Area