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Search results; Over 1,000 homes in Winter Haven

Guest favorite
Home in Winter Haven
Lakefront with a dock and tiki bar
3 bedrooms, 5 beds, 2 private baths
Aug 17 – 22
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4.89 out of 5 average rating, 47 reviews
Top guest favorite
Home in Winter Haven
Lakefront with a pool and private dock
4.98 out of 5 average rating, 121 reviews, 5 bedrooms, 7 beds, 3.5 baths
Nov 16 – 21
Top guest favorite
Home in Winter Haven
Lakefront with a private pool and lake views
5.0 out of 5 average rating, 42 reviews, 4 bedrooms, 4 beds, 2.5 baths
Aug 13 – 18
Guest favorite
Guesthouse in Winter Haven
Private dock on Lake Howard
4.98 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bath
Aug 15 – 20
Top guest favorite
Apartment in Winter Haven
Under a mile from LEGOLAND, with pool
4.98 out of 5 average rating, 44 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 17 – 22
Guest favorite
Home in Winter Haven
Lakefront with a heated pool and kayaks
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 6 beds, 3 baths
Aug 13 – 18
Top guest favorite
Condo in Winter Haven
Lake Lulu views from a screened patio
4.89 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 13 – 18
Guest favorite
Home in Winter Haven
Restored Spanish Gothic home with a fireplace
4.96 out of 5 average rating, 24 reviews, 2 bedrooms, 3 beds, 1 bath
Nov 23 – 28
Guest favorite
Guesthouse in Auburndale
Gated cottage with a game room
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 18 – 23
Home in Lake Hamilton
Lakefront home with stunning lake views
New place to stay, 5 bedrooms, 6 beds, 2 baths
Aug 29 – Sep 3
Home in Davenport
Private pool and grill near Disney
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 4 baths
Oct 5 – 10
Guest favorite
Room in Winter Haven
Private entrance, 10 minutes from Legoland
4.87 out of 5 average rating, 31 reviews, 1 queen bed, 1 bath
Aug 21 – 26
Top guest favorite
Home in Haines City
Private pool, 15 minutes from LEGOLAND
4.98 out of 5 average rating, 44 reviews, 4 bedrooms, 5 beds, 4.5 baths
Aug 16 – 21
Home in Davenport
Screened pool and spa near Disney
New place to stay, 4 bedrooms, 5 beds, 2 baths
Oct 2 – 7
Top guest favorite
Villa in Haines City
Gated villa with a pool and grill
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 29 – Sep 3
Top guest favorite
Home in Winter Haven
One-story home 5 miles from Legoland
4.96 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 11 – 16
Top guest favorite
Home in Davenport
Pool, spa, and cinema near Disney
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 5 beds, 3 baths
Sep 7 – 12
Home in Davenport
Private pool near Disney with free parking
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 19 – 24
Superhost
Home in Winter Haven
Spacious two-story near Lake Howard
3.5 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2.5 baths
Aug 15 – 20