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Our top choices for Windermere condo rentals

Condo in Kissimmee
Vacation Village Orlando, Celebration8.6 out of 10, Excellent, (3119)
$133 nightly
The price is $150
Jan 11 - Jan 12, 2026
Total with taxes and fees

10.0 out of 10, Exceptional, (1)

10.0 out of 10, Exceptional, (12)
$259 nightly
The price is $289
Jan 5 - Jan 6, 2026
Total with taxes and fees

Condo in Vacation Village
2 BR/2 bath Clermont cottage w/ Heated Olympic Pool/basketball/lake access10.0 out of 10, Exceptional, (4)
$244 nightly
The price is $268
Jan 14 - Jan 15, 2026
Total with taxes and fees

9.2 out of 10, Wonderful, (149)
$180 nightly
The price is $202
Jan 4 - Jan 5, 2026
Total with taxes and fees

Condo in Kissimmee
Warm and cozy 1 bed/1 bath Condo Just 7 miles from Disney!9.4 out of 10, Exceptional, (81)
$209 nightly
The price is $234
Jan 3 - Jan 4, 2026
Total with taxes and fees

Condo in Kissimmee
2bd/2ba condo close to Disney, Storey Lake10.0 out of 10, Exceptional, (5)
$270 nightly
The price is $301
Jan 6 - Jan 7, 2026
Total with taxes and fees

Condo in Kissimmee
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+29.6 out of 10, Exceptional, (193)
$218 nightly
The price is $244
Dec 28 - Dec 29
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windermere Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings
10/10 Excellent
Find out more about Windermere
Windermere Condo Rentals information
Number of reviews | 3,811 |
|---|---|
Accommodation | 5831 Condo Rentals |
Lowest Price | $150 |
Highest Price | $504 |
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