Best Vacation Homes in Windermere
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
3 Guests
Balcony/Terrace
Pet Friendly
Kitchen
Parking
US $116/Night
7 Nights - US $814
Villa
10.0(1 Review)
5 Bedrooms
3 Baths
11 Guests
3100.01 ft²
Pool- Balcony/Terrace
View- Pet Friendly
US $222/Night
7 Nights - US $1,554
Villa
1 Bedroom
1 Bath
Fireplace/Heating- Balcony/Terrace
- Pet Friendly
- Kitchen
US $592/Night
7 Nights - US $4,147
House
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $4,289/Night
7 Nights - US $30,023
Resort
9.4(74 Reviews)
9 Baths
18 Guests
630.46 ft²
Oceanfront
Hot Tub
Spa- Fireplace/Heating
US $275/Night
7 Nights - US $1,925
Cottage
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $196/Night
7 Nights - US $1,370
House
1 Bedroom
1 Bath
28 Guests
- Air Conditioner
- Internet
- Child Friendly
Security/Safety
US $91/Night
7 Nights - US $640
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $81/Night
7 Nights - US $567
Windermere Luxury Rentals
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $4,275/Night
7 Nights - US $29,925
House
10.0(61 Reviews)
4 Bedrooms
3 Baths
6 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $675/Night
7 Nights - US $4,725
Villa
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $551/Night
7 Nights - US $3,856
House
2.0(2 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $504/Night
7 Nights - US $3,527
US $422/Night
7 Nights - US $2,953
House
4 Bedrooms
3 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $402/Night
7 Nights - US $2,812
House
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $358/Night
7 Nights - US $2,508
House
5 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $354/Night
7 Nights - US $2,476
Windermere Pet Friendly Vacation Rentals
House
9.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $313/Night
7 Nights - US $2,189
Villa
9.0(2 Reviews)
3 Bedrooms
2 Baths
12 Guests
2825 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $244/Night
7 Nights - US $1,707
House
7.4(3 Reviews)
5 Bedrooms
2 Baths
7 Guests
2600 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $294/Night
7 Nights - US $2,056
Villa
6.0(7 Reviews)
5 Bedrooms
4 Baths
11 Guests
2847 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $258/Night
7 Nights - US $1,806
Villa
5 Bedrooms
4 Baths
11 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $340/Night
7 Nights - US $2,382
Villa
3 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $273/Night
7 Nights - US $1,910
House
5 Bedrooms
7 Baths
12 Guests
- Fireplace/Heating
- Pool
Breakfast- Pet Friendly
US $1,912/Night
7 Nights - US $13,383
House
5 Bedrooms
6 Baths
10 Guests
6596 ft²
Private Pool- Spa
- Fireplace/Heating
- Pool
US $771/Night
7 Nights - US $5,398
Windermere Large Vacation Homes
House
9.6(7 Reviews)
4 Bedrooms
3 Baths
20 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $351/Night
7 Nights - US $2,458
House
3 Bedrooms
2 Baths
10 Guests
1625.35 ft²
- Fireplace/Heating
- Pool
- Parking
- Internet
US $183/Night
7 Nights - US $1,281
House
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $284/Night
7 Nights - US $1,988
House
3 Bedrooms
2 Baths
10 Guests
1620 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $207/Night
7 Nights - US $1,447
House
8.0(1 Review)
5 Bedrooms
5 Baths
12 Guests
- Private Pool
- Pool
- Air Conditioner
- Internet
US $555/Night
7 Nights - US $3,882
House
4 Bedrooms
2 Baths
11 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $414/Night
7 Nights - US $2,898
House
8.6(18 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $338/Night
7 Nights - US $2,363
House
5 Bedrooms
3 Baths
16 Guests
- Kitchen
- Parking
- Internet
- Child Friendly
US $249/Night
7 Nights - US $1,741
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 673+ 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 956+ 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 436+ 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
- 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
- Remarkable House finding at 7.9m distance from Disney and 7.2m to OCCC
- Welcome to the Farm House! Excellent Location, Pet Friendly!
- 5bd Country Charm w/1Acre, Deck, Private space near Parks
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 55 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
Resort
9.2(1000 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Balcony/Terrace
US $289/Night
7 Nights - US $2,025
Apartment
7.2(5 Reviews)
1 Bedroom
1 Bath
6 Guests
548.96 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $153/Night
7 Nights - US $1,068
Apartment
6.0(1 Review)
1 Bedroom
1 Bath
- Pool
- Kitchen
- Air Conditioner
- Internet
US $169/Night
7 Nights - US $1,186
House
4 Bedrooms
4 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $1,809/Night
7 Nights - US $12,660
House
4 Bedrooms
5 Baths
8 Guests
4000 ft²
- Private Pool
- Spa
- Fireplace/Heating
- Pool
US $1,200/Night
7 Nights - US $8,400
House
6 Bedrooms
7 Baths
90 Guests
- Private Pool
- Pool
- Air Conditioner
- Child Friendly
US $724/Night
7 Nights - US $5,068
US $449/Night
7 Nights - US $3,143
House
3 Bedrooms
2 Baths
6 Guests
1713 ft²
- Fireplace/Heating
- Pool
Lake View- View
US $421/Night
7 Nights - US $2,944
