Windermere Short-Term Rentals

Windermere Short Term Stay

Orlando 20 Guest Villa Centrally Located with Game Room

9.6

Exceptional

(7 Reviews)

Orlando 20 Guest Villa Centrally Located with Game Room

20 Guests 4 Bedrooms 3 Bathrooms

Family Friendly House

Hot Tub
Fireplace/Heating
Kitchen

ZA R6,786/Night For 7 Nights ZA R47,503

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New

Sunrise On The Lake in Downtown Windermere

1713 ft² 6 Guests 3 Bedrooms 2 Bathrooms

Family Friendly House

Fireplace/Heating
Pool
Lake View

ZA R6,961/Night For 7 Nights ZA R48,727

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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

ZA R1,939/Night For 7 Nights ZA R13,572

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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

ZA R3,674/Night For 7 Nights ZA R25,721

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New

Rustic Hideaway - Great Location + Pet Friendly!

1 Bedroom 1 Bathroom

Family Friendly Villa

Fireplace/Heating
Balcony/Terrace
Pet Friendly

ZA R10,111/Night For 7 Nights ZA R70,774

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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

ZA R70,602/Night For 7 Nights ZA R494,208

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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

ZA R4,552/Night For 7 Nights ZA R31,861

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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

ZA R9,631/Night For 7 Nights ZA R67,414

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Shore Steps Cottage - Walking Distance To The Town Of Windermere

New Property

New

Shore Steps Cottage - Walking Distance To The Town Of Windermere

3 Guests 1 Bedroom 1 Bathroom

Family Friendly Cottage

Fireplace/Heating
Balcony/Terrace
Kitchen

ZA R3,444/Night For 7 Nights ZA R24,099

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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

ZA R4,689/Night For 7 Nights ZA R32,821

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New

Near Disney, amazing, private and comfortable room

28 Guests 1 Bedroom 1 Bathroom

House

Air Conditioner
Internet
Child Friendly

ZA R1,513/Night For 7 Nights ZA R10,593

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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

ZA R2,526/Night For 7 Nights ZA R17,677

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More Top-Rated Short Term Stay in Windermere Area

Why Choose Rent By Owner for your Windermere Short Term Stay?

What makes our Short Term Stay 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 Short Term Stay

Where are the best neighborhoods to stay in Windermere?

When choosing where to stay in Windermere, Florida, you’ll find neighborhoods that offer a peaceful and family-friendly atmosphere, perfect for relaxing getaways. Consider staying near the heart of Windermere for convenient access to local amenities and scenic views, or explore quieter residential areas for a more private retreat. Whatever your preference, these neighborhoods provide a dependable and comfortable base for your visit to this charming Florida town.

Bay Lake

This area offers convenient access to the region's popular attractions, making it an ideal choice for those seeking comfortable short term stays near the heart of the action. Staying here provides a relaxing retreat while remaining close to key entertainment hubs within the area.

View 566+ Rentals in Bay Lake

Southwest Orlando

Known for its accessible location, this neighborhood is perfect for travelers looking to enjoy easy drives to local attractions and amenities. It offers a peaceful environment with the convenience of nearby shopping, dining, and entertainment options for your stay.

View 916+ Rentals in Southwest Orlando

Metro West

Situated within a scenic part of the region, this neighborhood provides a tranquil setting while still being close to Orlando’s vibrant attractions. It’s an excellent choice for those seeking a balance of comfort and accessibility during their stay.

View 432+ Rentals in Metro West

Best Times to Visit Windermere

When should you plan your Short Term Stay stay?

Choosing the ideal time to vacation here can enhance your experience in this destination, as seasonal variations influence activities and weather, making it important to consider your preferred climate and crowd levels when planning your short term stay in the area.

Peak Season Highlights

Winter (December to February)

During these months, you will experience the highest demand for short term stays as visitors flock to enjoy the mild climate and festive events in the region.

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

Spring (March to May)

This period sees an influx of travelers seeking pleasant weather and blooming landscapes, making it a popular time for booking accommodations here.

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

Off-Season Highlights

Summer (June to August)

The summer months tend to be less crowded, offering more relaxed short term stay options with warmer temperatures and longer days.

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

Fall (September to November)

Autumn is a quieter season, providing a tranquil atmosphere ideal for those seeking a peaceful escape while enjoying cooler weather.

Average Temperature Daytime: 78°F - Nighttime: 58°F

Weekly Weather Forecast for Windermere

How to Book Your Windermere Short Term Stay

What's our booking process?

Our platform allows you to browse a curated selection of short term stay. 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 Short Term Stay in Windermere Area

Common Short Term Stay Amenities

What amenities can you expect?

Our Short Term Stay 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 access to private outdoor pools for relaxing swims under the Florida sun.
Take advantage of well-maintained outdoor patios or decks ideal for dining or lounging outside.
Experience the comfort of lush, landscaped gardens surrounding your rental in the area.
Make the most of spacious outdoor seating areas perfect for social gatherings or quiet evenings.
Benefit from outdoor grills or barbecues to prepare delicious meals with family and friends.
Utilize well-equipped outdoor sports facilities such as tennis courts or volleyball areas.
Stroll through scenic walking paths or trails nearby, showcasing the natural beauty of the region.

Top Attractions Around Windermere

What attractions are nearby?

Within this charming area, you can enjoy a variety of outdoor activities and scenic attractions that showcase the natural beauty and serene atmosphere of Windermere, Florida, making it an ideal destination for memorable short term stays where relaxation and exploration go hand in hand.

Family Activities

Lake Windermere Boat Tours Enjoy a family-friendly boat tour on the scenic waters, offering a relaxing way to explore the area's natural beauty.
Windermere Mini Golf Challenge each other to a fun-filled round of mini golf suitable for all ages in this family-oriented attraction.
Local Nature Trails Discover the region's lush landscapes with easy-to-navigate nature trails that provide opportunities for hiking, biking, and wildlife spotting.
Community Parks and Playgrounds Spend quality time at nearby parks with playgrounds and picnic areas, perfect for family gatherings and outdoor activities.

Adult Activities

Golfing at Windermere Club Experience a relaxing day on the beautifully maintained courses, perfect for golf enthusiasts seeking leisure and scenic views in this destination.
Lake Butler Trail Kayaking Enjoy exploring the tranquil waters of Lake Butler with kayak rentals, offering an ideal way to connect with nature in the region.
Visit to The Windermere Fine Art Gallery Discover local artists works and immerse yourself in the vibrant arts scene within this community-focused destination.
Shopping at Windermere Village Browse boutique stores and enjoy a leisurely shopping experience tailored to adult visitors interested in unique finds and local craftsmanship.

Other Places to Stay in Windermere, FL

Tibet Butler Preserve

Explore 94 Properties

Lake Butler

Explore 79 Properties

Isleworth Golf and Country Club

Explore 77 Properties

Windermere Country Club

Explore 64 Properties

More Places to Stay Near Windermere

Windermere Travel Tips

How Can You Make the Most of Your Stay?

Explore local outdoor activities: Take advantage of the region's scenic parks and lakes to enjoy activities like kayaking, paddleboarding, or cycling for a memorable experience during your visit.
Visit nearby dining options: Savor the diverse culinary scene around this destination by trying popular local restaurants that showcase regional flavors and hospitality.
Plan your transportation in advance: Utilize local shuttle services or rent a vehicle to easily access attractions and navigate the area comfortably during your stay.
Make the most of your short term stays: Take time to relax at your rental property, which often offers a home-like atmosphere, creating a perfect base for exploring this vibrant destination.

Transportation Options

Rental Car Services: Renting a vehicle is a flexible way to explore the area at your own pace, with several companies offering convenient pickup and drop-off options nearby.
Public Transportation: Local bus services provide an affordable and reliable means of traveling around the region, connecting you to key destinations within Windermere and beyond.
Taxi and Rideshare Options: Taxis and rideshare platforms like Uber and Lyft operate here, offering quick and comfortable transportation for short trips or airport transfers.
Bicycle Rentals: For a more active approach, bicycle rentals are available for exploring the scenic areas at a leisurely pace, ideal for enjoying the local ambiance.

Local Customs Options

Zoom Town Etiquette: Locals value a friendly and respectful demeanor, especially when navigating through the area's serene neighborhoods and local events.
Community Celebrations: Participating in or observing local festivals and parades is a cherished tradition that reflects the region’s vibrant community spirit.
Environmental Respect: There is a strong emphasis on preserving the natural beauty of the area, so respectful outdoor behavior is highly encouraged during visits.
Dining Customs: Supporting local eateries with customary tipping practices and courteous manners enhances your experience here.

Frequently Asked Questions About Windermere Short-term Rentals

1. What are the top Short Term Stays 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 Short Term Stays in Windermere:

2. How many Short Term Stays are available in Windermere?

Currently, the total number of properties listed by RBO in 2026 is over 2 in the Windermere area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Short Term Stays 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 outlined for each short term stay before completing your booking to understand any applicable fees or restrictions.

4. How do I find out about availability for my preferred travel dates?

Availability details are provided on each property listing. To confirm your dates, you can check directly on the listing page or contact the property owner for real-time updates.

5. Are there any specific house rules or guest requirements I should be aware of?

Yes, each short term stay will have its own set of house rules and guest requirements outlined in the listing description. It's recommended that you read these carefully before booking to ensure a smooth stay.

6. Is there a minimum stay requirement for booking here?

Minimum stay requirements are specified on each property listing. Be sure to verify the length of stay needed for your visit before proceeding with your reservation.

7. What amenities are typically included in these short term stays?

The amenities offered vary by property, but common features include Wi-Fi, parking, kitchens, and air conditioning. For specific amenities, refer to the individual listing details or contact the host directly.