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We found 24,144 vacation rentals — enter your dates for availability
Discover a selection of more than 10,000 vacation rentals in Windermere that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $100 per night, and houses and condos are popular options for a stay in Windermere. Either way, you'll find a rental for everyone's needs.
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Destination guide
The charming city of Windermere awaits you
The beaches and surrounding scenery provide a peaceful ambiance to your vacation home in Windermere. Well known for its restaurants, shopping and sporting events, this romantic city won't disappoint. Walt Disney World® and Universal Studios Florida™ are just a couple of the must-sees in the area. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.
Activities
Sightseeing in and around Windermere
Are you looking for things to do in the city? Venture out of your vacation home and check out everything that makes Windermere a one-of-a-kind vacation spot. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:
- Walt Disney World® (4.8 mi / 7.7 km)
- Universal Studios Florida™ (4.8 mi / 7.7 km)
- SeaWorld® Orlando (7.2 mi / 11.6 km)
- Magic Kingdom® Park (4.8 mi / 7.7 km)
- Universal’s Islands of Adventure™ (5.1 mi / 8.2 km)
- Epcot® (7.1 mi / 11.5 km)
Natural features
Exploring the natural landscape of Windermere
Whether you're looking for adventure or just want to spend some time taking in the scenery, Windermere is a great place to spend some time outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:
- Lake Butler (0.6 mi / 1 km)
- Tibet Butler Preserve (2.8 mi / 4.5 km)
- Turkey Lake Park (4.5 mi / 7.2 km)
- Lake Eve (7.7 mi / 12.4 km)
- Little Lake Bryan (7.7 mi / 12.4 km)
- Lake Bryan (8.5 mi / 13.7 km)
How to get there
How to get to and around Windermere
Fly into Kissimmee, FL (ISM-Kissimmee Gateway), the closest airport, located 14.7 mi (23.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Orlando, FL (MCO-Orlando Intl.), which is 15.2 mi (24.5 km) away.
How many vacation rentals are available around Windermere?
Our 2021 property listings offer a large selection of 24,144 vacation rentals around Windermere. From 18,306 house rentals to 4,221 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.