Windermere beach rentals

We found 745 beach rentals — enter your dates for availability

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September 2025

October 2025

Explore Windermere beach rentals

Spacious 4-bedroom house in wonderful Orlando with AC, WiFi

Sleeps 12 · 4 bedrooms · 2+ bathrooms

Large pool heated in the winter. Lovely lake by pool

CHECKIN TODAY 89+/N OCT 1-OCT 4, 13-19 LOVELY 2.5 BDRS 2 BTHS LAKE VIEW BALCONY

Sleeps 8 · 3 bedrooms · 2 bathrooms

Private pool/Spa in the backyard with nice view

Beautiful Family Home, private Pool/Spa, Great View, Gated Resort near Disney

Sleeps 16 · 7 bedrooms · 4+ bathrooms

7BR/Pool/Covered Lanai/Game room/WiFi, near Disney and golf

Gorgeous, Private Pool, Covered Lanai, Gated Resort, Near Orlando Disney

Sleeps 16 · 7 bedrooms · 4+ bathrooms

Top rated beach rentals - Windermere

Premier Host

Excellent family home

Beautifully presented home with excellent facilities that catered well for our family get together. The children loved the games room and the swimming pool.

Julie F.

Stayed Jul 2025

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