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Search results; Over 1,000 homes in Windermere

Guest favourite
Guest house in Windermere
Paradise nook near Orlando's theme parks
1 bedroom, 2 beds, 1 private bathroom
17–22 Aug
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4.91 out of 5 average rating, 290 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds, 3.5 bathrooms
9–14 Sept
New place to stay
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.96 out of 5 average rating, 25 reviews
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
New place to stay
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 84 reviews
Villa in Kissimmee
Spacious villa w/pool & spa & game room
5 bedrooms, 7 beds, 5 bathrooms
27 Dec – 1 Jan
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 94 reviews
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 4 reviews
Flat in Orlando
Cute, cozy condo - Universal walk
2 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
New place to stay
Home in Kissimmee
Golden Haven | 5BR | Pool | 12 Min to Disney
5 bedrooms, 7 beds, 4.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds, 4 bathrooms
27 Jan – 1 Feb
5.0 out of 5 average rating, 6 reviews
Home in Kissimmee
Brisa Family Retreat with Private Pool
3 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
22–27 Nov
4.98 out of 5 average rating, 46 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
New place to stay
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
2 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 104 reviews
Top guest favourite
Home in Kissimmee
Cozy nd peaceful home w/ lake, near Disney Parks!
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jan
5.0 out of 5 average rating, 8 reviews