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Search results; Over 1,000 homes in Winter Haven

Guest favourite
Guest house in Winter Haven
Charming Lakeside Cottage
1 bedroom, 1 bed, 1 private bathroom
1–6 Sept
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4.98 out of 5 average rating, 125 reviews
Flat in Winter Haven
One of the best in Polk
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
New place to stay
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, 123 reviews
Top guest favourite
Home in Winter Haven
Winter Haven Waterfront Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 42 reviews
Guest favourite
Home in Winter Haven
Lakefront home w/heated pool minutes from Legoland
5 bedrooms, 7 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Room in Winter Haven
Peace and Love Room 1B Private Entrance
1 queen bed, 1 bathroom
1–6 Sept
4.87 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Winter Haven
Luxury by Legoland 106
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Winter Haven
Lovely Home on Lilac Lane - Winter Haven
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Room in Winter Haven
Quiet & safe, for one or two.
2 single beds, 1 bathroom
1–6 Sept
4.96 out of 5 average rating, 105 reviews
Villa in Haines City
6BR Lake View Home | Private Pool | Near Legoland
6 bedrooms, 8 beds, 5.5 bathrooms
1–6 Sept
New place to stay
Guest favourite
Home in Winter Haven
Beautiful Lake Front Cottage
3 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 15 reviews
Home in Lake Hamilton
Spacious Lakefront 5BR home, Near Disney, Legoland
5 bedrooms, 6 beds, 2 bathrooms
6–11 Sept
New place to stay
Villa in Haines City
4BR Themed Villa | Pool & Cinema | Balmoral
4 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
New place to stay
Guest favourite
Room in Winter Haven
Historic touch private Ensuite in Winter Haven
2 queen beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Apartment in Winter Haven
Waterfront Condo | Pool & Dock | Near Legoland
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
4.89 out of 5 average rating, 9 reviews
Guest favourite
Home in Haines City
Minniehaha Castle
4 bedrooms, 7 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Winter Haven
Roomy 3BR Near Lake Howard & Downtown Winter Haven
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
3.5 out of 5 average rating, 4 reviews
Home in Lakeland
Lake House - Beautiful Views, Spacious & Modern
4 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds, 8 bathrooms
13–18 Sept