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Search results; Over 1,000 homes in Winter Haven

Guest favourite
Home in Winter Haven
Legoland Lakehouse Canoe&Kayak Retreat
3 bedrooms, 3 beds, 3 private bathrooms
13–18 Aug
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4.92 out of 5 average rating, 212 reviews
Top guest favourite
Home in Winter Haven
Family Friendly Lake House W/ Pool Near Legoland
5 bedrooms, 7 beds, 3.5 bathrooms
26–31 Jul
4.98 out of 5 average rating, 109 reviews
Top guest favourite
Home in Winter Haven
Adult-Only Getaway w/ Mermaid Pool | 18+, Private
4 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.98 out of 5 average rating, 123 reviews
Top guest favourite
Guest house in Winter Haven
Charming Lakeside Cottage
1 bedroom, 1 queen bed, 1 bathroom
22–27 Jun
5.0 out of 5 average rating, 117 reviews
Top guest favourite
Home in Winter Haven
Winter Haven Waterfront Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
16–21 Jun
5.0 out of 5 average rating, 39 reviews
Guest favourite
Home in Winter Haven
Lakefront home w/heated pool minutes from Legoland
5 bedrooms, 7 beds, 3 bathrooms
3–8 Jul
5.0 out of 5 average rating, 6 reviews
Place to stay in Winter Haven
Guest Room B
1 bedroom, 1 single bed, 1 bathroom
16–21 Jun
Superhost
Home in Kissimmee
2026 Themed NEW 08 Bedrooms At Solara Resort
8 bedrooms, 11 beds, 7.5 bathrooms
28 Nov – 3 Dec
Superhost
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
29 May – 3 Jun
5.0 out of 5 average rating, 3 reviews
Room in Winter Haven
05-Downtown Winter Haven Private Suite
1 bed, 1 bathroom
22–27 Jun
Top guest favourite
Flat in Winter Haven
Luxury by Legoland 106
2 bedrooms, 4 beds, 2 bathrooms
29 Jun – 4 Jul
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Haines City
Florida Dream Home
4 bedrooms, 5 beds, 4.5 bathrooms
17–22 Jun
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Guest house in Dundee
New Modern Guest House! Great location. Smoke-Free
1 bedroom, 1 queen bed, 1 bathroom
16–21 Jun
4.97 out of 5 average rating, 39 reviews
Superhost
Home in Kissimmee
Brand new pool /spa summer kitchen near clubhouse
7 bedrooms, 8 beds, 6.5 bathrooms
3–8 Aug
New place to stay
Top guest favourite
Home in Davenport
5BR Villa |2 Game Rooms |Heated Pool| 10 min Parks
5 bedrooms, 13 beds, 3 bathrooms
16–21 Jun
4.98 out of 5 average rating, 43 reviews
Villa in Haines City
Fairway Oasis - Southern Dunes - Golf Course
4 bedrooms, 6 beds, 2 bathrooms
16–21 Jun
Superhost
Home in Kissimmee
Ultimate Privacy, Pool & Spa, Theater, Near Disney
5 bedrooms, 6 beds, 4 bathrooms
21–26 Jun
New place to stay
Superhost
Townhouse in Clermont
Mario Arcade & Wizard Magic @ Windsor Cay
5 bedrooms, 8 beds, 5.5 bathrooms
29 Aug – 3 Sept
New place to stay
Superhost
Home in Orlando
11BR Brand New | Themed Rooms | Sleeps 24 - 11121
11 bedrooms, 15 beds, 11.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 3 reviews