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Search results; Over 1,000 homes in Winter Haven

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Guest favourite
Cottage in Winter Haven
2 - Ships Ahoy Bungalow 2 bed/2 bath - Unit 17
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
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4.87 out of 5 average rating, 179 reviews
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Top guest favourite
Home in Winter Haven
Winter Haven Waterfront Retreat
4 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 42 reviews
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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, 125 reviews
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Guest favourite
Guest house in Winter Haven
Charming Lakeside Cottage
1 bedroom, 1 queen bed
1–6 Sept
4.98 out of 5 average rating, 126 reviews
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Top guest favourite
Room in Winter Haven
Quiet & safe, for one or two.
2 single beds
1–6 Sept
4.96 out of 5 average rating, 105 reviews
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Top guest favourite
Flat in Winter Haven
Luxury by Legoland 106
2 bedrooms, 4 beds
7–12 Sept
4.98 out of 5 average rating, 46 reviews
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Flat in Winter Haven
One of the best in Polk
2 bedrooms, 2 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Room in Winter Haven
Peace and Love Room 1B Private Entrance
1 queen bed
1–6 Sept
4.87 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Winter Haven
Lovely Home on Lilac Lane - Winter Haven
3 bedrooms, 3 beds
18–23 Sept
4.96 out of 5 average rating, 26 reviews
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Guest favourite
Home in Winter Haven
Beautiful Lake Front Cottage
3 bedrooms, 6 beds
1–6 Sept
5.0 out of 5 average rating, 15 reviews
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Villa in Haines City
6BR Lake View Home | Private Pool | Near Legoland
6 bedrooms, 8 beds
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Home in Auburndale
Pleasant 4 Bed, 2 Bath Home with Screened Pool
4 bedrooms, 4 beds
15–20 Sept
New place to stay
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Guest favourite
Room in Winter Haven
Historic touch private Ensuite in Winter Haven
2 queen beds
1–6 Sept
5.0 out of 5 average rating, 10 reviews
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Home in Winter Haven
Rustic Private Home/Self Check-In/ Near Legoland
1 bedroom, 2 beds
7–12 Sept
New place to stay
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Superhost
Room in Winter Haven
Comfortable room
1 small double bed
10–15 Sept
New place to stay
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Top guest favourite
Apartment in Winter Haven
Waterfront Condo | Pool & Dock | Near Legoland
2 bedrooms, 2 beds
6–11 Sept
4.89 out of 5 average rating, 9 reviews
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Home in Kissimmee
Pool Home 10min from Disney
4 bedrooms, 8 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Room in Winter Haven
Cozy room near Legoland/WinterHaven Hospital/CDL.
1 queen bed
1–6 Sept
4.9 out of 5 average rating, 89 reviews
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Guest favourite
Cottage in Lake Wales
Lake Wales Vacation Rental w/ Screened-In Porch!
3 bedrooms, 4 beds
6–11 Sept
4.98 out of 5 average rating, 54 reviews