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  5. Vacation Rentals with Pools

Windermere Vacation Rentals with Pools

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6.0 (1 Review)
Apartment
  • Air Conditioner
  • Pool
  • Security/Safety

Why Choose Rent By Owner for your Windermere Vacation Rentals with Pools?

What makes our Vacation Rentals with Pools 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 Windermere

When should you plan your Vacation Rentals with Pools stay?

Choosing the optimal time to vacation in this destination ensures you enjoy perfect weather and maximize your experience with rentals featuring pools, whether visiting during the warm summer months or the shoulder seasons when the area offers a more tranquil environment.

Peak Season Highlights

spring
Spring (March to May)

During spring, you’ll experience warmer weather and blooming scenery, making it an ideal time to enjoy your stay with a pool in this destination.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
winter
Winter Holidays (December to February)

The winter holiday season offers mild temperatures and festive vibes, providing a cozy atmosphere for relaxing by your rental with a pool in the area.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Summer (June to August)

In summer, the region sees high temperatures and crowds, but it remains a favorite time for those seeking warm weather and poolside enjoyment.

Average Temperature Daytime: 85°F to 95°F - Nighttime: 70°F to 75°F
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Early Fall (September to October)

Early fall features cooler temperatures and fewer visitors, making it an excellent choice for a peaceful retreat with a pool here.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Weekly Weather Forecast for Windermere

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.

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 to relax and cool off under the sun in your Windermere vacation home.
  • Benefit from outdoor loungers and seating areas ideal for soaking up the Florida sunshine.
  • Take advantage of barbecue grills for outdoor dining and family cookouts by the poolside.
  • Make use of spacious patios or decks perfect for entertaining guests or enjoying scenic views.
  • Find convenient outdoor shower facilities to rinse off after swimming or outdoor activities.
  • Explore landscaped gardens and lush greenery that enhance your outdoor living experience here.
  • Access outdoor lighting features that allow you to enjoy the pool area comfortably during evening hours.
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Family Activities

  • Lake Windermere Boat Tours Experience the scenic beauty of this area by taking a family-friendly boat tour across Lake Windermere, offering memorable views and outdoor fun.
  • Windermere Recreation Park Enjoy a day of picnicking, playground fun, and sports activities at this local park suitable for all ages, perfect for relaxing with your loved ones.
  • Wildlife Viewing in the Region Discover the diverse wildlife that inhabits nearby nature reserves and preserves, ideal for educational outings and nature walks.
  • Local Community Events Participate in seasonal festivals and family-oriented events that showcase the vibrant culture of this destination, providing entertainment for everyone.
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Adult Activities

  • Lake Windermere Cruises Enjoy a relaxing boat cruise across the picturesque lake, offering stunning views and a tranquil escape in the area.
  • Windermere Golf Club Tee off at this renowned golf course that provides a challenging and scenic experience for golf enthusiasts visiting here.
  • Downtown Windermere Shops & Dining Explore charming boutiques and indulge in local cuisine within the vibrant downtown district of this destination.
  • Regional Nature Trails Discover scenic walking and biking trails that showcase the natural beauty of the surrounding region, perfect for outdoor activities.

Other Places to Stay in Windermere, FL

Tibet Butler Preserve
Isleworth Golf and Country Club
Windermere Country Club

Windermere Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Take advantage of the area’s serene setting by scheduling outdoor activities that allow you to unwind by your rentals with pools and enjoy the natural beauty around.
  • Choose a Rental with Pool Access: Opt for accommodations that feature private or shared pools to maximize relaxation and refreshment during your stay here.
  • Explore Local Dining Options: Discover nearby restaurants and cafes to experience the region’s culinary flavors after a day spent exploring or lounging poolside.
  • Stay Connected and Informed: Use local resources and maps to navigate easily around this destination, ensuring you make the most of every moment in the region.

Transportation Options

  • Rental Car Services: Renting a vehicle is a flexible way to explore the region, offering convenience and freedom when traveling around Windermere and nearby attractions.
  • Taxi and Rideshare Options: Taxis and rideshare services like Uber and Lyft provide quick and reliable transportation for short trips within this destination.
  • Public Transportation: Local bus services offer an affordable option for navigating the area, making it easy to reach various points of interest without hassle.
  • Private Shuttle Services: Private shuttles can be booked for personalized transfers, ideal for seamless travel between your rentals with pools and key locations around here.

Local Customs Options

  • Southern Hospitality: Visitors often experience a warm welcome and friendly interactions that reflect the region's reputation for hospitality when they visit this destination.
  • Local festivals and events, especially during holidays, showcase lively traditions that bring the community together in celebration.
  • Respect for Nature: It’s customary here to observe environmentally friendly practices, especially around the area’s natural lakes and green spaces, ensuring their preservation.
  • Community Engagement: Participating in local activities and supporting small businesses is a valued customs that enhances your connection with this welcoming region.

Frequently Asked Questions About Windermere Rentals with Pools

1. How many Rentals With Pools are available in Windermere?

Currently, the total number of properties listed by RBO in 2026 is over 12 in the Windermere area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Windermere. 

2. What is the cancellation policy for rentals with pools in Windermere, Florida?

Cancellation policies vary depending on the specific property. You should review the listing details or contact the owner directly to understand their cancellation terms and any associated fees.

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

Additional fees, such as cleaning or service charges, can vary by property. Please check the listing details or reach out to the owner for precise information regarding any extra costs.

4. How do I confirm the availability of a rentals with pools during my desired travel dates?

Availability is shown on each listing; however, it’s advisable to contact the property owner directly to verify current availability and secure your booking promptly.

5. What amenities and features are typically included in rentals with pools in this area?

Properties often come with amenities like private pools, fully equipped kitchens, Wi-Fi, and outdoor living spaces. Check individual listings for specific features included in your preferred rental.

6. Is it possible to modify or cancel my booking if my plans change after reservation?

Modification and cancellation options depend on the property owner’s policies. Review the listing’s terms or contact the owner directly to understand your options should your plans change.