Windermere Cottage Rentals
Cottage
1 Bedroom
1 Bath
3 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
R5,774/Night
7 Nights - R40,414
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
Pet Friendly- Kitchen
- Parking
R1,803/Night
7 Nights - R12,629
Villa
10.0(1 Review)
5 Bedrooms
3 Baths
11 Guests
3100.01 ft²
Pool- Balcony/Terrace
View- Pet Friendly
R3,595/Night
7 Nights - R25,162
Villa
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R9,592/Night
7 Nights - R67,146
House
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
R69,067/Night
7 Nights - R483,461
Resort
9.4(74 Reviews)
9 Baths
18 Guests
630.46 ft²
Oceanfront
Hot Tub
Spa- Fireplace/Heating
R4,453/Night
7 Nights - R31,169
House
1 Bedroom
1 Bath
28 Guests
- Air Conditioner
- Internet
- Child Friendly
Security/Safety
R1,480/Night
7 Nights - R10,363
Apartment
7.2(5 Reviews)
1 Bedroom
1 Bath
6 Guests
548.96 ft²
- Oceanfront
- Hot Tub
- Pool
Ocean View
R2,471/Night
7 Nights - R17,292
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
R1,312/Night
7 Nights - R9,181
House
3 Bedrooms
2 Baths
10 Guests
1625.35 ft²
- Fireplace/Heating
- Pool
- Parking
- Internet
R2,963/Night
7 Nights - R20,741
House
10.0(61 Reviews)
4 Bedrooms
3 Baths
6 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R10,929/Night
7 Nights - R76,505
House
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R5,509/Night
7 Nights - R38,568
People Visiting Windermere Also Like
Why Choose Rent By Owner for your Windermere Cottage Rentals?
What makes our Cottage 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.
Weekly Weather Forecast for Windermere
How to Book Your Windermere Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage 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
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Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windermere
Common Cottage Rentals Amenities
What amenities can you expect?
Our Cottage 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
Other Places to Stay in Windermere, FL
Tibet Butler Preserve
Lake Butler
Isleworth Golf and Country Club
Windermere Country Club
Frequently Asked Questions About Windermere Rental Cottages
1. What are the top Cottages 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 Cottages 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 Cottages are available in Windermere?
Currently, the total number of properties listed by RBO in 2026 is over 1 in the Windermere area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Windermere.
More Rentals You May Like Near Windermere
House
9.6(7 Reviews)
4 Bedrooms
3 Baths
20 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
R5,686/Night
7 Nights - R39,799
House
9.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R5,063/Night
7 Nights - R35,443
Villa
9.0(2 Reviews)
3 Bedrooms
2 Baths
12 Guests
2825 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,948/Night
7 Nights - R27,639
House
7.4(3 Reviews)
5 Bedrooms
2 Baths
7 Guests
2600 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R4,755/Night
7 Nights - R33,290
Villa
6.0(7 Reviews)
5 Bedrooms
4 Baths
11 Guests
2847 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,178/Night
7 Nights - R29,242
House
4.8(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
R4,842/Night
7 Nights - R33,889
House
2.0(2 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
R8,158/Night
7 Nights - R57,107
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R69,218/Night
7 Nights - R484,529
R6,831/Night
7 Nights - R47,813
House
4 Bedrooms
3 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R6,505/Night
7 Nights - R45,530
House
5 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R5,726/Night
7 Nights - R40,090
Villa
5 Bedrooms
4 Baths
11 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
R5,511/Night
7 Nights - R38,568
