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 house rentals in Winter Haven
House rentals with a pool
Home in Davenport
4.95 out of 5 average rating, 161 reviewsDOLPHIN COVE NEAR DISNEY
20–27 Jan
Home in Davenport
4.98 out of 5 average rating, 104 reviewsSunset Villa
2–9 Sept
Home in Auburndale
4.94 out of 5 average rating, 146 reviewsLake Whistler Beach House with lakefront pool
6–13 Aug
Home in Davenport
4.87 out of 5 average rating, 120 reviewsDisney getaway
16–23 Jan
Home in Davenport
4.9 out of 5 average rating, 104 reviewsCharming Home near Disney with Private Heated Pool
31 Oct – 7 Nov
Home in Davenport
4.81 out of 5 average rating, 131 reviewsWelcoming fully equipped villa in Davenport
15–22 Jan
Home in Davenport
4.79 out of 5 average rating, 102 reviewsMintra’s Villa Pool & Spa
28 Aug – 4 Sept
Home in Winter Haven
4.94 out of 5 average rating, 16 reviewsKid-friendly Home w/ Pool & BBQ
6–13 Nov
Weekly house rentals
Home in Winter Haven
4.89 out of 5 average rating, 37 reviewsNewly remodeled House 3BR/2BA
13–20 Apr
Home in Lake Alfred
4.95 out of 5 average rating, 40 reviewsCentral FL Bungalow! 2BR/1B With Fully Fenced Yard
10–17 Jan
Home in Winter Haven
5.0 out of 5 average rating, 14 reviewsScottlee's Magnolia Farmhouse
25 Nov – 2 Dec
Home in Winter Haven
4.94 out of 5 average rating, 18 reviewsOverlook Joy
20–27 Dec
Home in Winter Haven
4.96 out of 5 average rating, 45 reviewsThe Family Friendly Fun House
6–13 Jan
Home in Winter Haven
5.0 out of 5 average rating, 3 reviewsPeaceful Lakeside Escape
15–22 Aug
Home in Lake Wales
4.96 out of 5 average rating, 28 reviewsLa Casita Redonda
30 Oct – 6 Nov
Home in Winter Haven
5.0 out of 5 average rating, 11 reviewsCozy Legoland Pool House
22–29 Sept
Private house rentals
Home in Lake Wales
4.86 out of 5 average rating, 51 reviewsHidden Gem - Hot Tub/ Fire pit/Hammock/Grill Area
12–19 Aug
Home in Lakeland
4.99 out of 5 average rating, 97 reviewsSwan Studio Lakeland
23–30 Oct
Home in Lakeland
4.96 out of 5 average rating, 79 reviewsCozy Lake House Retreat - Amazing Views !
7–14 Nov
Home in Lakeland
5.0 out of 5 average rating, 20 reviewsModern 2 Queens-Walk to Downtown
7–14 Sept
Home in Davenport
4.95 out of 5 average rating, 59 reviewsSweet vacation home.
13–20 Jul
Home in Haines City
4.81 out of 5 average rating, 16 reviewsVilla Blanca Villa Villa
9–16 Apr
Home in Winter Haven
4.88 out of 5 average rating, 52 reviews3-br peaceful home near Legoland
11–18 Aug
Home in Auburndale
4.9 out of 5 average rating, 21 reviewsA Cozy Place!
11–18 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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