House holiday rentals in Winter Haven
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Top-rated house rentals in Winter Haven
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Haven house rentals
House rentals with a pool
Home in Davenport
4.95 out of 5 average rating, 161 reviewsDOLPHIN COVE NEAR DISNEY
26 Apr – 3 May
Home in Lakeland
4.86 out of 5 average rating, 108 reviewsHollingsworth Pool Home
23–30 Aug
Home in Auburndale
4.94 out of 5 average rating, 146 reviewsLake Whistler Beach House with lakefront pool
2–9 Jan
Home in Davenport
4.87 out of 5 average rating, 135 reviewsInsta-worthy getaway near Disney w/ free parking!💎
27 Sep – 4 Oct
Home in Davenport
4.9 out of 5 average rating, 105 reviewsCharming Home near Disney with Private Heated Pool
28 Oct – 4 Nov
Home in Davenport
4.87 out of 5 average rating, 121 reviewsDisney getaway
25 Oct – 1 Nov
Home in Davenport
4.78 out of 5 average rating, 130 reviewsBeautiful 4 bed home, south-facing pool,games room
10–17 May
Home in Davenport
4.79 out of 5 average rating, 102 reviewsMintra’s Villa Pool & Spa
18–25 Sep
Weekly house rentals
Home in Winter Haven
5.0 out of 5 average rating, 14 reviewsScottlee's Magnolia Farmhouse
25 Nov – 2 Dec
Home in Lake Alfred
4.95 out of 5 average rating, 41 reviewsCentral FL Bungalow! 2BR/1B With Fully Fenced Yard
16–23 Jan
Home in Winter Haven
4.94 out of 5 average rating, 18 reviewsOverlook Joy
11–18 Dec
Home in Winter Haven
4.96 out of 5 average rating, 46 reviewsThe Family Friendly Fun House
13–20 Jan
Home in Winter Haven
5.0 out of 5 average rating, 3 reviewsPeaceful Lakeside Escape
6–13 Oct
Home in Winter Haven
4.98 out of 5 average rating, 54 reviewsBeautiful home near downtown - 15 min to Legoland!
17–24 Sep
Home in Winter Haven
5.0 out of 5 average rating, 12 reviewsCozy Legoland Pool House
15–22 Jun
Home in Lake Wales
4.96 out of 5 average rating, 28 reviewsLa Casita Redonda
22–29 Dec
Private house rentals
Home in Winter Haven
5.0 out of 5 average rating, 33 reviews341 Legoland Sherman's Antiques Lake Silver
11–18 May
Home in Winter Haven
5.0 out of 5 average rating, 11 reviewsCozy Lakefront Home w/ Pool -7 mins from Legoland
13–20 Oct
Home in Winter Haven
4.93 out of 5 average rating, 27 reviewsParaiso de relax Legoland
4–11 Jan
Home in Davenport
5.0 out of 5 average rating, 14 reviewsSpacious House Near Attractions
12–19 Dec
Home in Lakeland
4.99 out of 5 average rating, 97 reviewsSwan Studio Lakeland
30 May – 6 Jun
Home in Winter Haven
5.0 out of 5 average rating, 17 reviewsCozy on the Canal near Legoland
8–15 Oct
Home in Winter Haven
4.91 out of 5 average rating, 33 reviewsLake Front Lego Land Estate
1–8 May
Home in Auburndale
4.9 out of 5 average rating, 21 reviewsA Cozy Place!
14–21 Dec
Quick stats about house rentals in Winter Haven
Total rentals
260 properties
Rentals with dedicated workspaces
150 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
170 properties are a good fit for families
Total number of reviews
8.3K reviews
Destinations to explore
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