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Search results; Over 1,000 homes in Winter Haven

Home in Winter Haven
Live your best Florida life!
3 bedrooms, 2 bathrooms
14–19 Sept
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4.8 out of 5 average rating, 59 reviews
Top guest favourite
Home in Lakeland
Family Heated Pool Home Sleep 12 Near Tampa Disney
4 bedrooms, 7 beds
14–19 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Davenport
Mickey themed villa/pool & Gameroom/mins to disney
3 bedrooms, 6 beds
14–19 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Winter Haven
Winter Haven Waterfront Retreat
4 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Winter Haven
Family Friendly Lake House W/ Pool Near Legoland
5 bedrooms, 7 beds
16–21 Nov
4.98 out of 5 average rating, 126 reviews
Home in Winter Haven
Pool+Jacuzzi+Game/Movie Rm+Near Legoland/Downtown
4 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Home in Haines City
Amazing pool house in Southern Dunes!
4 bedrooms, 6 beds
14–19 Sept
New place to stay
Top guest favourite
Home in Davenport
Josh & Megan’s Place
5 bedrooms, 10 beds
23–28 Oct
4.99 out of 5 average rating, 96 reviews
Top guest favourite
Home in Haines City
Florida Dream Home
4 bedrooms, 5 beds
14–19 Sept
4.98 out of 5 average rating, 44 reviews
Guest favourite
Guest house in Auburndale
The Auburndale Cottage―Game Room―Central Florida
2 bedrooms, 3 beds
15–20 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Davenport
6BR family retreat w/ pool & game room
6 bedrooms, 7 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Home in Davenport
Megan and Josh's Place
4 bedrooms, 5 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 53 reviews
Home in Haines City
Cozy 6BR Balmoral Retreat | Pool, Spa & Waterpark
6 bedrooms
20–25 Sept
Top guest favourite
Flat in Winter Haven
Luxury by Legoland 106
2 bedrooms, 4 beds
14–19 Sept
4.98 out of 5 average rating, 47 reviews
Guest favourite
Guest house in Winter Haven
Charming Lakeside Cottage
1 bedroom, 1 queen bed
19–24 Sept
4.98 out of 5 average rating, 128 reviews
Home in Davenport
Hidden Lagoon: 5BR Pool Home, Close to Disney
5 bedrooms, 7 beds
21–26 Sept
New place to stay
Guest favourite
Home in Winter Haven
Beautiful Lake Front Cottage
3 bedrooms, 6 beds
14–19 Sept
5.0 out of 5 average rating, 15 reviews
Villa in Haines City
Fairway Oasis - Southern Dunes - Golf Course
4 bedrooms, 6 beds
21–26 Sept
Top guest favourite
Home in Davenport
4BR themed villa w/ pool & balcony
4 bedrooms, 8 beds
16–21 Sept
4.98 out of 5 average rating, 58 reviews