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Search results; Over 1,000 homes in Winter Haven

Guest favourite
Cottage in Winter Haven
2 - Ships Ahoy Bungalow 2 bed/2 bath - Unit 17
2 bedrooms, 4 beds, 2 bathrooms
29 Sept – 4 Oct
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4.87 out of 5 average rating, 181 reviews
Top guest favourite
Home in Winter Haven
Winter Haven Waterfront Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Haines City
Florida Dream Home
4 bedrooms, 5 beds, 4.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 44 reviews
Home in Haines City
Amazing pool house in Southern Dunes!
4 bedrooms, 6 beds, 3 bathrooms
13–18 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, 126 reviews
Home in Winter Haven
Pool+Jacuzzi+Game/Movie Rm+Near Legoland/Downtown
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
New place to stay
Guest favourite
Guest house in Auburndale
The Auburndale Cottage―Game Room―Central Florida
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Lakeland
Family Heated Pool Home Sleep 12 Near Tampa Disney
4 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 49 reviews
Room in Winter Haven
Lovely Lakefront Stay w/Queen Bed
1 queen bed, 1 bathroom
1–6 Jan
5.0 out of 5 average rating, 4 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, 96 reviews
Top guest favourite
Home in Davenport
Megan and Josh's Place
4 bedrooms, 5 beds, 3 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Home in Davenport
6BR family retreat w/ pool & game room
6 bedrooms, 7 beds, 4 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Winter Haven
Luxury by Legoland 106
2 bedrooms, 4 beds, 2 bathrooms
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, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 128 reviews
Home in Haines City
Cozy 6BR Balmoral Retreat | Pool, Spa & Waterpark
6 bedrooms, 6.5 bathrooms
20–25 Sept
Top guest favourite
Home in Lakeland
Luxury Pool Retreat | Heated Pool & Pet Friendly
5 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
4.95 out of 5 average rating, 66 reviews
Home in Davenport
Hidden Lagoon: 5BR Pool Home, Close to Disney
5 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
New place to stay
Home in Auburndale
Pleasant 4 Bed, 2 Bath Home with Screened Pool
4 bedrooms, 4 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 3 reviews
Home in Winter Haven
Charlie’s Choice: Your Perfect Home Base
4 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews