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Search results; Over 1,000 homes in Windermere

Home in Ocoee

Serenity Retreat

2 bedrooms, 2 beds, 2 bathrooms

10–15 Aug

$972 SGD for 5 nights

New place to stay

Superhost

Townhouse in Kissimmee

SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney

4 bedrooms, 8 beds, 3.5 bathrooms

17–22 Aug

5.0 out of 5 average rating, 3 reviews

Superhost

Townhouse in Clermont

5 BD/ 4.5 BA/ Windsor Cay (16218 CC)

5 bedrooms, 7 beds, 4.5 bathrooms

18–23 Oct

$1,886 SGD for 5 nights

Top guest favourite

Home in Four Corners

Luxury 05 Bedroom at Windsor Cay

5 bedrooms, 7 beds, 4.5 bathrooms

25–30 Aug

5.0 out of 5 average rating, 29 reviews

Flat in Kissimmee

Vacation Condo with pool-20 Min from Disney

3 bedrooms, 4 beds, 2 bathrooms

9–14 Aug

$963 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Superhost

Home in Orlando

Next Epic Universe, OCC, Disney @Vista Cay home

3 bedrooms, 4 beds, 3.5 bathrooms

5–10 Aug

$1,531 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Home in Kissimmee

Modern Disney Villa • 7BR • Private Pool

7 bedrooms, 9 beds, 6.5 bathrooms

4–9 Aug

New place to stay

Superhost

Home in Four Corners

7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)

7 bedrooms, 10 beds, 5.5 bathrooms

23–28 Aug

$1,990 SGD for 5 nights

Flat in Orlando

Cute, cozy condo - Universal walk

2 bedrooms, 4 beds, 2 bathrooms

26 Sept – 1 Oct

$742 SGD for 5 nights

New place to stay

Superhost

Home in Kissimmee

6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)

6 bedrooms, 8 beds, 4 bathrooms

10–15 Aug

$1,444 SGD for 5 nights

Superhost

Townhouse in Clermont

5 Bd/ 5.5 Ba/ Windsor Cay (16123 Cl)

5 bedrooms, 7 beds, 5.5 bathrooms

23–28 Aug

$1,725 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Home in Orlando

Henry Balch Landing

4 bedrooms, 5 beds, 3 bathrooms

5–10 Aug

$1,435 SGD for 5 nights

New place to stay

Superhost

Home in Four Corners

2026 Themed 07 Bedrooms At Windsor Cay

7 bedrooms, 8 single beds, 5 bathrooms

28 Aug – 2 Sept

Top guest favourite

Home in Ocoee

Lakefront in West Orlando Florida

3 bedrooms, 4 beds, 2 bathrooms

9–14 Aug

$2,261 SGD for 5 nights

4.91 out of 5 average rating, 93 reviews

Superhost

Home in Clermont

Pool, hot tub & arcade - 19 mins to Disney

4 bedrooms, 5 beds, 2 bathrooms

10–15 Aug

Extended stay discount

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Davenport

Pool Spa + Outdoor Entertainment | Golf Retreat

4 bedrooms, 6 beds, 5 bathrooms

16–21 Aug

$2,253 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

Superhost

Townhouse in Clermont

5BR Private Pool Home at Windsor Cay Near Disney

5 bedrooms, 7 beds, 4.5 bathrooms

16–21 Aug

$1,335 SGD for 5 nights

New place to stay

Home in Winter Park

Luxury Designer Home • Downtown,Universal & Disney

4 bedrooms, 4 beds, 3.5 bathrooms

4–9 Aug

5.0 out of 5 average rating, 5 reviews