Best Vacation Homes in Windermere
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $120/Night
For 7 Nights US $838
3100.01 ft²
11 Guests
5 Bedrooms
3 Bathrooms
Villa
- Pool
- Balcony/Terrace
- View
US $222/Night
For 7 Nights US $1,554
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $611/Night
For 7 Nights US $4,276
6 Guests
2 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $4,266/Night
For 7 Nights US $29,859
630.46 ft²
18 Guests
59 Bedrooms
9 Bathrooms
Free Cancellation
Resort
- Oceanfront
- Hot Tub
- Spa
US $275/Night
For 7 Nights US $1,925
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $196/Night
For 7 Nights US $1,370
28 Guests
1 Bedroom
1 Bathroom
House
- Air Conditioner
- Internet
- Child Friendly
US $91/Night
For 7 Nights US $640
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $81/Night
For 7 Nights US $567
Windermere Luxury Rentals
6 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $4,275/Night
For 7 Nights US $29,925
14 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $1,809/Night
For 7 Nights US $12,660
2000 ft²
6 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $675/Night
For 7 Nights US $4,725
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $582/Night
For 7 Nights US $4,073
11 Guests
5 Bedrooms
2 Bathrooms
Pet Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
US $504/Night
For 7 Nights US $3,527
12 Guests
4 Bedrooms
4 Bathrooms
Group Friendly
House
- Private Pool
- Pool
- Air Conditioner
US $422/Night
For 7 Nights US $2,953
20 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Kitchen
US $410/Night
For 7 Nights US $2,870
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $402/Night
For 7 Nights US $2,812
Windermere Pet Friendly Vacation Rentals
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $308/Night
For 7 Nights US $2,156
6705.92 ft²
8 Guests
4 Bedrooms
3 Bathrooms
House
- Private Pool
- Fireplace/Heating
- Pool
US $283/Night
For 7 Nights US $1,983
2825 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $287/Night
For 7 Nights US $2,008
8 Guests
5 Bedrooms
4 Bathrooms
Pet Friendly
House
- Pet Friendly
- Air Conditioner
- Internet
US $343/Night
For 7 Nights US $2,399
2600 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $294/Night
For 7 Nights US $2,056
2847 ft²
11 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $349/Night
For 7 Nights US $2,445
11 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $370/Night
For 7 Nights US $2,591
10 Guests
5 Bedrooms
4 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $354/Night
For 7 Nights US $2,476
Windermere Large Vacation Homes
11 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $295/Night
For 7 Nights US $2,062
1625.35 ft²
10 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Pool
- Parking
US $183/Night
For 7 Nights US $1,281
11 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $285/Night
For 7 Nights US $1,996
1620 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $250/Night
For 7 Nights US $1,748
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Air Conditioner
US $555/Night
For 7 Nights US $3,882
12 Guests
5 Bedrooms
7 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Breakfast
US $1,912/Night
For 7 Nights US $13,383
6596 ft²
10 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Spa
- Fireplace/Heating
US $771/Night
For 7 Nights US $5,398
11 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Parking
- Air Conditioner
US $414/Night
For 7 Nights US $2,898
Why Choose Rent By Owner for your Windermere Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals
Where are the best neighborhoods to stay in Windermere?
When exploring Windermere, Florida, choosing the right neighborhood can elevate your vacation experience to new heights. Each area offers unique charm and convenient access to local amenities, making it easy to find the perfect setting for your stay. Whether you prefer a peaceful retreat or a lively community atmosphere, Windermere's neighborhoods provide a diverse range of options that cater to different preferences. By selecting a well-suited location, you can enjoy a seamless and memorable visit to this beautiful Florida destination.
Bay Lake
Located within close proximity to the area’s renowned attractions, Bay Lake offers convenient access to the region’s vibrant entertainment scene and picturesque scenery, making it an ideal choice for those seeking a memorable stay in this destination.
View 930+ Rentals in Bay LakeSouthwest Orlando
This part of the region provides easy connectivity to popular attractions and amenities, ensuring your stay here is both comfortable and practical for exploring the best that the area has to offer.
View 929+ Rentals in Southwest OrlandoMetro West
Offering a blend of suburban tranquility and accessibility, Metro West is perfect for visitors looking to enjoy a peaceful retreat while remaining close to the key sites and activities in this lively region.
View 433+ Rentals in Metro WestBest Times to Visit Windermere
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the region offers ideal conditions for enjoying your stay whether you prefer warm, sunny days or cooler, quieter months.
Peak Season Highlights
Spring (March to May)
During the spring months, you will experience warm daytime temperatures ideal for enjoying the outdoor scenery and local activities.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Winter Holidays (December to February)
The winter season offers cooler weather and festive atmosphere, making it a popular time to explore the area with fewer crowds.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Summer (June to August)
Though summer is warmer, it tends to be less crowded, offering a more relaxed experience for those seeking tranquility and comfort.
Average Temperature Daytime: 85-95°F - Nighttime: 65-75°F
Fall (September to November)
In fall, the region features milder weather and fewer visitors, making it an excellent choice for peaceful getaways.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Weekly Weather Forecast for Windermere
How to Book Your Windermere Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Windermere
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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 lounge areas with comfortable seating to relax and unwind.
- Take advantage of private pools perfect for cooling off during warm days.
- Make the most of lush backyard spaces ideal for outdoor dining or picnics.
- Utilize dedicated BBQ grills for preparing delicious meals al fresco.
- Explore landscaped gardens that enhance the outdoor ambiance of your stay.
- Benefit from spacious patios or decks offering scenic views of the surrounding area.
- Participate in recreational activities such as outdoor sports or games in open yards.
Top Attractions Around Windermere
What attractions are nearby?
During your stay here, you'll find a variety of outdoor recreational activities and scenic spots nearby to enhance your visit in this charming region.
Family Activities
- Lake Windermere Cruises: Enjoy a relaxing boat tour around the region’s scenic lake, providing an enjoyable family outing with stunning views and wildlife spotting.
- Windermere Sports Complex: Engage in sports and outdoor activities at this family-friendly facility that offers courts, fields, and recreation areas for all ages.
- Local Parks and Playgrounds: Spend quality time at nearby parks featuring playgrounds, picnic areas, and open spaces perfect for children to play and families to unwind.
- Community Events and Festivals: Participate in seasonal events and festivals hosted throughout the year, offering entertainment and cultural experiences for families visiting here.
Adult Activities
- Distillery Tours: Explore local craft distilleries to sample unique spirits and learn about their production process in this charming destination.
- Golfing Experiences: Tee off at premier golf courses renowned for their picturesque landscapes and challenging fairways here in the region.
- Lake Activities: Enjoy fishing, paddleboarding, or tranquil boat rides on the nearby lakes that offer a perfect escape into nature’s serenity.
- Dining Out: Indulge in diverse culinary experiences at highly rated restaurants that showcase the area’s vibrant food scene.
Other Places to Stay in Windermere, FL
Tibet Butler Preserve
Lake Butler
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 region’s popular outdoor spots and local amenities by scheduling your activities ahead to maximize your stay.
- Select Convenient Accommodation Locations: Choose a vacation rental close to key attractions and transportation options to reduce travel time and enhance your experience here.
- Explore Local Dining and Shopping: Immerse yourself in the area's culture by trying nearby restaurants and browsing charming shops during your visit.
- Check Guest Reviews and Ratings: Review feedback on properties to find the most reliable and well-maintained vacation rentals that meet your expectations in this destination.
Transportation Options
- Rental Car Services: Renting a car gives you the flexibility to explore the scenic region and visit nearby attractions at your own pace.
- Local Taxis and Rideshare Options: Convenient for quick trips around town or airport transfers, ensuring reliable transportation during your stay.
- Public Transportation: Local bus services provide an economical way to navigate here without the hassle of parking or driving yourself.
- Shuttle Services: Many vacation rentals in this area offer convenient shuttle options that connect you to key destinations effortlessly.
Local Customs Options
- Southern Hospitality: You’ll notice that greeting visitors warmly is a cherished tradition here, reflecting the friendly spirit of this welcoming community.
- Local Dining Etiquette: When enjoying meals at neighborhood eateries, it’s common to share dishes and engage in friendly conversation, embodying the region’s communal vibe.
- Community Events: Participating in local festivals or outdoor gatherings offers a great way to experience the area's rich customs and connect with residents.
- Respect for Nature: The region values its natural beauty, so you are encouraged to follow eco-friendly practices during outdoor activities and preserve the environment.
Windermere Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals 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 Vacation Rentals in Windermere:
- The Home of Sweet Peace
- Beautiful 4 Bedroom Home
- Remarkable House finding at 7.9m distance from Disney and 7.2m to OCCC
- Luxury Retreat in Windermere The Perfect Base for Exploring Orlando
- New 1 Bedroom suite with full kitchen, living room and bathroom
- Orlando 20 Guest Villa Centrally Located with Game Room
- Arnold Palmer's Bay Hill Club & Lodge
- Arnold Palmer's Bay Hill Club & Lodge
- 3860 - Wonderful and Modern House with pool Close Disney
- Welcome to the Farm House! Excellent Location, Pet Friendly!
2. How many vacation rentals have private pools in Windermere?
There are 1 vacation rentals with private pools near Windermere. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windermere are best for families?
If you are looking for a family-friendly vacation home in Windermere, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windermere:
4. How many Rentbyowner vacation rentals are available in Windermere?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 56 in the Windermere 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 Windermere.
5. What is the cancellation policy for vacation rentals in Windermere, Florida?
Cancellation policies vary by property. Please review the specific listing details or contact the property owner directly to understand the terms and any applicable fees before booking your stay.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or security deposits may apply. It’s best to consult the listing or contact the owner for a complete breakdown of all costs involved.
7. How do I ensure my reservation is secured after booking?
Once you complete the booking process and submit your payment, your reservation is confirmed. For added peace of mind, verify all details with the property owner and keep confirmation emails handy.
8. Can I modify or cancel my reservation if my plans change?
Modification and cancellation options depend on the property's policies. Review the specific listing's cancellation terms or reach out directly to the owner for guidance regarding any changes to your stay.
9. What amenities are typically included in vacation rentals in this region?
Most rentals offer amenities like Wi-Fi, fully equipped kitchens, private pools, and outdoor spaces. To confirm the available amenities, check the property description or contact the owner before booking.
Windermere Top Rated Vacation Rentals
US $366/Night
For 7 Nights US $2,559
548.96 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Pool
US $153/Night
For 7 Nights US $1,068
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Kitchen
- Air Conditioner
US $169/Night
For 7 Nights US $1,186
4000 ft²
8 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Spa
- Fireplace/Heating
US $1,200/Night
For 7 Nights US $8,400
90 Guests
6 Bedrooms
7 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Air Conditioner
US $724/Night
For 7 Nights US $5,068
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
US $449/Night
For 7 Nights US $3,143
1713 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Lake View
US $421/Night
For 7 Nights US $2,944
2342 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $404/Night
For 7 Nights US $2,829
