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Search results; Over 1,000 homes in Winter Haven

Guest favourite
Cottage in Winter Haven
Sweet Cottage - 5 mi to Legoland & 0.5 mi to Dtwn
2 bedrooms, 5 beds, 1.5 private bathrooms
13–18 Sept
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4.81 out of 5 average rating, 235 reviews
Home in Winter Haven
Pool+Jacuzzi+Game/Movie Rm+Near Legoland/Downtown
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 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 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
Top guest favourite
Home in Winter Haven
Lovely Home on Lilac Lane - Winter Haven
3 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Winter Haven
Lakefront home w/heated pool minutes from Legoland
5 bedrooms, 7 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 11 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
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
Room in Winter Haven
Quiet & safe, for one or two.
2 single beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 105 reviews
Guest favourite
Home in Winter Haven
Beautiful Lake Front Cottage
3 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 15 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
Apartment in Winter Haven
Waterfront Condo | Pool & Dock | Near Legoland
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Lakeland
Edinger's Nest
4 bedrooms, 6 beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 63 reviews
Home in Auburndale
Pleasant 4 Bed, 2 Bath Home with Screened Pool
4 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Winter Haven
Cozy room near Legoland/WinterHaven Hospital/CDL.
1 queen bed, 1 bathroom
14–19 Sept
4.9 out of 5 average rating, 89 reviews
Top guest favourite
Home in Davenport
Large Pool & Spa Near Disney | Big Family Memories
4 bedrooms, 6 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 21 reviews
Home in Lakeland
Fully Furnished 3BR Lake Hollingsworth Oasis
3 bedrooms, 5 beds, 1 bathroom
29 Sept – 4 Oct
New place to stay
Guest favourite
Cottage in Lake Wales
Lake Wales Vacation Rental w/ Screened-In Porch!
3 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
4.98 out of 5 average rating, 55 reviews
Superhost
Home in Davenport
Bridgeford Splash Retreat
4 bedrooms, 6 beds, 3 bathrooms
26–31 Oct
New place to stay