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Search results; Over 1,000 homes in Winter Haven

Guest favourite
Cottage in Winter Haven
Sweet Cottage - 5 mi to Legoland & 0.5 mi to Dtwn
2 bedrooms, 5 beds, 1.5 private bathrooms
6–11 Sept
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4.81 out of 5 average rating, 235 reviews
Top guest favourite
Home in Winter Haven
Family Friendly Lake House W/ Pool Near Legoland
5 bedrooms, 7 beds, 3.5 bathrooms
16–21 Nov
4.98 out of 5 average rating, 126 reviews
Top guest favourite
Home in Winter Haven
Winter Haven Waterfront Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 42 reviews
Home in Davenport
Hidden Lagoon: 5BR Pool Home, Close to Disney
5 bedrooms, 7 beds, 3 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Home in Haines City
Florida Dream Home
4 bedrooms, 5 beds, 4.5 bathrooms
5–10 Sept
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Home in Davenport
6BR pool retreat - game room & EV charger
6 bedrooms, 7 beds, 4 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Home in Davenport
Josh & Megan’s Place
5 bedrooms, 10 beds, 5 bathrooms
23–28 Oct
4.99 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Winter Haven
Luxury by Legoland 106
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 46 reviews
Superhost
Home in Haines City
Posh and Peaceful Golf Resort Gate Home w Pool
4 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Lakeland
Family Heated Pool Home Sleep 12 Near Tampa Disney
4 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Davenport
4BR family villa w/ pool & balcony
4 bedrooms, 8 beds, 3 bathrooms
16–21 Sept
4.98 out of 5 average rating, 55 reviews
Home in Davenport
The Palm w/ themed rooms private pool near Disney
4 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
New place to stay
Guest favourite
Guest house in Winter Haven
Charming Lakeside Cottage
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 126 reviews
Top guest favourite
Home in Lakeland
Lakeland Retreat: Private Heated Pool & Yard Games
3 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 36 reviews
Flat in Winter Haven
One of the best in Polk
2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Davenport
Star Wars & Wizard Themed XL Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Davenport
The New Woodlands Villa | 4 Bed 3 Bath Villa
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Davenport
Magic Place | 15 Min Disney Park |Heated Pool |BBQ
4 bedrooms, 6 beds, 4.5 bathrooms
4–9 Sept
4.99 out of 5 average rating, 83 reviews
Villa in Haines City
4BR Themed Villa | Pool & Cinema | Balmoral
4 bedrooms, 6 beds, 3 bathrooms
21–26 Sept
New place to stay