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Search results; Over 1,000 homes in Winter Haven

Top guest favourite
Flat in Winter Haven
Florida Penthouse in luxurious mansion!
1 bedroom, 1 bed, 1 private bathroom
12–17 Aug
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4.98 out of 5 average rating, 179 reviews
Top guest favourite
Home in Winter Haven
Winter Haven Waterfront Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
12–17 Aug
5.0 out of 5 average rating, 42 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, 121 reviews
Guest favourite
Guest house in Winter Haven
Charming Lakeside Cottage
1 bedroom, 1 queen bed, 1 bathroom
15–20 Aug
4.98 out of 5 average rating, 125 reviews
Guest favourite
Home in Winter Haven
Beautiful Lake Front Cottage
3 bedrooms, 6 beds, 3 bathrooms
12–17 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Winter Haven
Luxury by Legoland 106
2 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Villa in Haines City
Family 3BR Pool Home Near Disney w/ Private Patio
3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 16 reviews
Home in Haines City
Minniehaha Castle
4 bedrooms, 7 beds, 3 bathrooms
25–30 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Room in Auburndale
Private King Bed Near I-4 | Fast Wi-Fi & Parking
1 king bed, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Room in Winter Haven
Peace and Love Room 1B Private Entrance
1 queen bed, 1 bathroom
21–26 Aug
4.87 out of 5 average rating, 31 reviews
Guest favourite
Home in Winter Haven
Cozy Castle
2 bedrooms, 3 beds, 1 bathroom
23–28 Nov
4.96 out of 5 average rating, 24 reviews
Villa in Haines City
Fairway Oasis - Southern Dunes - Golf Course
4 bedrooms, 6 beds, 2 bathrooms
12–17 Aug
Home in Lakeland
Lake House - Beautiful Views, Spacious & Modern
4 bedrooms, 5 beds, 3 bathrooms
16–21 Aug
Guest favourite
Guest house in Auburndale
The Auburndale Cottage―Game Room―Central Florida
2 bedrooms, 3 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 8 reviews
Home in Lake Hamilton
Spacious Lakefront 5BR home, Near Disney, Legoland
5 bedrooms, 6 beds, 2 bathrooms
29 Aug – 3 Sept
New place to stay
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
14–19 Sept
Home in Davenport
Davenport Disney Destination w/Pool
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Winter Haven
Waterfront Condo | Pool & Dock | Near Legoland
2 bedrooms, 2 beds, 2 bathrooms
13–18 Aug
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Haines City
Florida Dream Home
4 bedrooms, 5 beds, 4.5 bathrooms
12–17 Aug
4.98 out of 5 average rating, 44 reviews