Windermere Accommodations

Apartment

New 1 Bedroom suite with full kitchen, living room and bathroom

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 3 Guests

R1,879/Night 7 Nights - R13,160

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Villa

Luxury Retreat in Windermere The Perfect Base for Exploring Orlando

10.0

Exceptional

(1 Review)

5 Bedrooms 3 Baths 11 Guests 3100.01 ft²

R3,589/Night 7 Nights - R25,123

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The Farm House - Great Location + Pet Friendly!

Villa

The Farm House - Great Location + Pet Friendly!

1 Bedroom 1 Bath

R9,793/Night 7 Nights - R68,546

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House

150-Yards To Arnold Palmer’s Bay Hill Clubhouse!

2 Bedrooms 2 Baths 6 Guests

R69,339/Night 7 Nights - R485,368

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Resort

Arnold Palmer's Bay Hill Club & Lodge

9.4

Exceptional

(74 Reviews)

9 Baths 18 Guests 630.46 ft²

R4,446/Night 7 Nights - R31,121

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House

Near Disney, amazing, private and comfortable room

1 Bedroom 1 Bath 28 Guests

R1,478/Night 7 Nights - R10,347

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Apartment

Resort condo near Disney Free parks shuttle

7.2

Very Good

(5 Reviews)

1 Bedroom 1 Bath 6 Guests 548.96 ft²

R2,468/Night 7 Nights - R17,266

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Apartment

1 Bedroom Lofted, Private entrance, dedicated parking, W/D, WiFi

1 Bedroom 1 Bath 2 Guests

R1,309/Night 7 Nights - R9,166

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7 Mi to Disney World: Orlando Home w/Private Pool

House

7 Mi to Disney World: Orlando Home w/Private Pool

3 Bedrooms 2 Baths 10 Guests 1625.35 ft²

R2,958/Night 7 Nights - R20,709

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Highly Rated

House

The Home of Sweet Peace

10.0

Exceptional

(61 Reviews)

4 Bedrooms 3 Baths 6 Guests 2000 ft²

R10,912/Night 7 Nights - R76,387

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House

Beautiful 4 Bedroom Home

10.0

Exceptional

(1 Review)

4 Bedrooms 4 Baths 8 Guests

R5,791/Night 7 Nights - R40,546

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House

Orlando 20 Guest Villa Centrally Located with Game Room

9.6

Exceptional

(7 Reviews)

4 Bedrooms 3 Baths 20 Guests

R5,677/Night 7 Nights - R39,737

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More Top-Rated Accommodations in Windermere Area

Why Choose Rent By Owner for your Windermere Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Windermere Accommodations

Where are the best neighborhoods to stay in Windermere?

For a memorable stay in Windermere, Florida, consider neighborhoods that offer convenient access to local attractions and serene surroundings. These areas provide a perfect balance of privacy and activity, ensuring you experience the best of what the region has to offer. Whether you prefer quiet residential streets or lively community hubs, you'll find options that cater to your travel preferences while enjoying the welcoming atmosphere of Windermere, Florida.

Bay Lake

Located adjacent to the region’s most popular attractions, Bay Lake offers convenient access to the area's vibrant entertainment and natural scenery. Staying here places you near the heart of the area’s dynamic attractions, making it an ideal choice for those seeking a central location.

View 672+ Rentals in Bay Lake

Southwest Orlando

This part of the region is known for its diverse amenities and peaceful surroundings, perfect for travelers looking to enjoy a quiet retreat while remaining close to the area's major attractions. Here, you can experience a balance of tranquility and accessibility during your stay.

View 942+ Rentals in Southwest Orlando

Metro West

A popular neighborhood that combines urban convenience with family-friendly environments, Metro West provides easy access to shopping, dining, and entertainment venues. Choosing accommodations here means being well-positioned to explore all that the area has to offer.

View 436+ Rentals in Metro West

Best Times to Visit Windermere

When should you plan your Accommodations stay?

To make the most of your visit, consider planning your vacation during the shoulder seasons when the area offers pleasant weather and fewer crowds, ensuring a more relaxing experience within this popular Florida destination.

Peak Season Highlights

Spring (March to May)

During spring, the area experiences pleasant weather perfect for enjoying outdoor activities while exploring the region’s scenic beauty.

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

Winter Holidays (December to February)

This period sees a surge of visitors taking advantage of cooler temperatures and festive celebrations, making it an ideal time for booking accommodations in this destination.

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

Off-Season Highlights

Summer (June to August)

While summer offers warm weather, this is also the less busy season here, giving you a more relaxed experience and better availability when booking your stay.

Average Temperature Daytime: 85-95°F - Nighttime: 70-80°F

Fall (September to November)

Autumn brings cooler days and fewer crowds, making it an excellent time to secure accommodations without the peak-season prices and enjoy a quieter visit.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F

Weekly Weather Forecast for Windermere

How to Book Your Windermere Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Windermere

More Top-Rated Accommodations in Windermere Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations 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 outdoor pool facilities for relaxing swims under the sun.
Take advantage of lush private gardens or landscaped yards for outdoor leisure.
Make use of patio areas equipped with tables and chairs for al fresco dining.
Experience outdoor grilling with designated barbecue areas on the property.
Access to scenic walking trails or bike paths nearby for outdoor adventures.
Relax in spacious lanai or covered porch spaces perfect for lounging.
Benefit from secure parking areas designed for your convenience during outdoor excursions.

Top Attractions Around Windermere

What attractions are nearby?

When visiting this destination, you'll find a variety of outdoor activities such as boating, fishing, and scenic nature walks nearby, making it an ideal spot to explore the natural beauty and tranquil surroundings of Windermere, Florida.

Family Activities

Windsor Hills Butterfly Garden Discover a lush outdoor space perfect for family strolls and educational encounters with native butterflies.
Lake Activities at Lake Windermere Enjoy paddle boating, fishing, or simply relaxing by the water in this scenic area ideal for family outings.
Orlando Tree Trek Adventure Park Experience an exhilarating outdoor adventure with treetop courses that challenge and entertain visitors of all ages.
Visit Local Playgrounds and Parks Spend quality time at family-friendly parks equipped with playgrounds and open spaces to unwind and have fun together.

Adult Activities

Lake Windsong Park Enjoy a relaxing day outdoors at this scenic park, perfect for picnics, walking trails, and appreciating the natural beauty of the area.
Windermere Historical Museum Discover the rich history and heritage of the region through engaging exhibits that provide insights into local life and culture.
Golfing at Windermere Club Tee off at this renowned golf course offering stunning views and a challenging layout, ideal for both beginners and experienced golfers.
Shopping and Dining Experiences Explore charming shops and dine at local restaurants that showcase the flavors and craftsmanship unique to the vicinity.

Other Places to Stay in Windermere, FL

Windermere Travel Tips

How Can You Make the Most of Your Stay?

Plan ahead for outdoor activities Take advantage of the area's pleasant climate by scheduling outdoor excursions early in the day to enjoy the natural beauty around here.
Explore local dining options Discover the region's culinary scene by trying nearby restaurants and cafes that showcase local flavors and ingredients.
Book your stay in advance To secure the best accommodations, especially during peak seasons, it's advisable to reserve your property through trusted platforms here well ahead of time.
Take advantage of nearby amenities Make the most of the community facilities and recreational spots available close to your accommodations to enhance your visit here.

Transportation Options

Personal Vehicle Rental: Renting a car offers you the flexibility to explore Windermere and its surroundings at your own pace, making it an ideal transportation option for your stay.
Shuttle Services: Many local shuttle services provide convenient transfers between major points of interest and nearby airports, ensuring a hassle-free experience while visiting this region.
Taxi and Rideshare: Taxis and rideshare options like Uber and Lyft are readily available in the area, providing quick and reliable transportation without the need for parking or driving yourself.
Bicycle Rentals: For a more active way to see the sights, renting a bicycle is an environmentally friendly choice that allows you to enjoy the scenic views here at your leisure.

Local Customs Options

Respect for Local Etiquette: When visiting, you’ll find that courteous manners and respect for community traditions are highly valued here in the region.
Celebration of Local Festivals: Participating in or observing vibrant festivals is a common way to embrace the area’s cultural heritage during your stay.
Environmental Awareness: Eco-friendly practices and conservation efforts are important here, so consider engaging in sustainable behaviors during your visit.
Community Hospitality: The locals are known for their welcoming spirit, making it easy for visitors to feel at home while exploring this destination.

Frequently Asked Questions about Windermere Accommodations

1. What are the top Accommodations in Windermere?

There are a lot of options in Windermere. If you plan on staying in the Windermere area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Windermere:

2. How many Accommodations are available in Windermere?

Currently, the total number of properties listed by RBO in 2026 is over 53 in the Windermere area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Windermere. 

3. What is the cancellation policy for bookings in this area?

Cancellation policies vary depending on the property listing. You should review the specific terms and conditions detailed on the listing page or contact the property owner directly to understand the cancellation options and any applicable fees.

4. Are there any additional fees I should be aware of when booking?

Additional fees, such as cleaning fees or service charges, are typically outlined on the listing. For a clear understanding of all costs involved, please check the detailed description or reach out to the host before confirming your reservation.

5. How can I secure my reservation during peak travel times?

To ensure your stay during busy seasons, it’s advisable to book well in advance. Confirm availability and any special requirements directly with the property owner through the listing's communication options.

6. What amenities are included with the accommodations here?

Amenities vary by property but are generally listed on each property’s page. For specific features like Wi-Fi, parking, or kitchen facilities, review the listing details or contact the host directly for more information.

7. Is there a minimum stay requirement for bookings in this destination?

Minimum stay policies depend on the individual property. To find out if there are any length-of-stay restrictions, please consult the listing details or contact the host prior to booking.