Windermere Accommodations

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

10.0

Exceptional

(1 Review)

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

3 Guests 1 Bedroom 1 Bathroom

Family Friendly Apartment

Balcony/Terrace
Pet Friendly
Kitchen

CA $162/Night For 7 Nights CA $1,135

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Luxury Retreat in Windermere The Perfect Base for Exploring Orlando

10.0

Exceptional

(1 Review)

Luxury Retreat in Windermere The Perfect Base for Exploring Orlando

3100.01 ft² 11 Guests 5 Bedrooms 3 Bathrooms

Villa

Pool
Balcony/Terrace
View

CA $307/Night For 7 Nights CA $2,151

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New

Rustic Hideaway - Great Location + Pet Friendly!

1 Bedroom 1 Bathroom

Family Friendly Villa

Fireplace/Heating
Balcony/Terrace
Pet Friendly

CA $846/Night For 7 Nights CA $5,919

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

New Property

New

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

6 Guests 2 Bedrooms 2 Bathrooms

House

Fireplace/Heating
Air Conditioner
Internet

CA $5,905/Night For 7 Nights CA $41,335

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9.4

Exceptional

(74 Reviews)

Arnold Palmer's Bay Hill Club & Lodge

630.46 ft² 18 Guests 59 Bedrooms 9 Bathrooms

Free Cancellation Resort

Oceanfront
Hot Tub
Spa

CA $381/Night For 7 Nights CA $2,665

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New

The Farm House - Great Location + Pet Friendly!

1 Bedroom 1 Bathroom

Family Friendly Villa

Fireplace/Heating
Balcony/Terrace
Pet Friendly

CA $805/Night For 7 Nights CA $5,638

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New

Near Disney, amazing, private and comfortable room

28 Guests 1 Bedroom 1 Bathroom

House

Air Conditioner
Internet
Child Friendly

CA $127/Night For 7 Nights CA $886

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3860 - Wonderful and Modern House with pool Close Disney

9.1

Exceptional

(7 Reviews)

3860 - Wonderful and Modern House with pool Close Disney

6705.92 ft² 8 Guests 4 Bedrooms 3 Bathrooms

House

Private Pool
Fireplace/Heating
Pool

CA $392/Night For 7 Nights CA $2,745

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New

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

2 Guests 1 Bedroom 1 Bathroom

Family Friendly Apartment

Fireplace/Heating
Pool
Balcony/Terrace

CA $112/Night For 7 Nights CA $785

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Resort Family Suite near Disney Pool view Free parks shuttle

7.2

Very Good

(5 Reviews)

Resort Family Suite near Disney Pool view Free parks shuttle

548.96 ft² 6 Guests 1 Bedroom 1 Bathroom

Ocean View Apartment

Oceanfront
Hot Tub
Pool

CA $211/Night For 7 Nights CA $1,478

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Highly Rated

10.0

Exceptional

(61 Reviews)

The Home of Sweet Peace

2000 ft² 6 Guests 4 Bedrooms 3 Bathrooms

Ocean View House

Oceanfront
Fireplace/Heating
Ocean View

CA $934/Night For 7 Nights CA $6,541

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New

7 Mi to Disney World Orlando Home with Private Pool

1625.35 ft² 10 Guests 3 Bedrooms 2 Bathrooms

House

Fireplace/Heating
Pool
Parking

CA $253/Night For 7 Nights CA $1,773

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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 543+ 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 913+ 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 432+ 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

Tibet Butler Preserve

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Lake Butler

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Isleworth Golf and Country Club

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Windermere Country Club

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More Places to Stay Near Windermere

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 54 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.