House vacation 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.
Vacation 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
Jan 22 – 29
Home in Auburndale
4.94 out of 5 average rating, 146 reviewsLake Whistler Beach House with lakefront pool
Mar 18 – 25
Home in Lakeland
4.86 out of 5 average rating, 108 reviewsHollingsworth Pool Home
Apr 18 – 25
Home in Davenport
4.87 out of 5 average rating, 122 reviewsDisney getaway
Nov 16 – 23
Home in Davenport
4.9 out of 5 average rating, 105 reviewsCharming Home near Disney with Private Heated Pool
Oct 28 – Nov 4
Home in Davenport
4.87 out of 5 average rating, 135 reviewsInsta-worthy getaway near Disney w/ free parking!💎
Sep 27 – Oct 4
Home in Davenport
4.8 out of 5 average rating, 136 reviewsKing bed pool in 4 corners area near shopping
Sep 7 – 14
Home in Davenport
4.81 out of 5 average rating, 131 reviewsWelcoming fully equipped villa in Davenport
Jan 9 – 16
Weekly house rentals
Home in Winter Haven
5.0 out of 5 average rating, 14 reviewsScottlee's Magnolia Farmhouse
Dec 7 – 14
Home in Winter Haven
4.97 out of 5 average rating, 64 reviewsThe Dalt Retreat
Dec 8 – 15
Home in Winter Haven
4.84 out of 5 average rating, 19 reviewsElohim Guest House (Cozy House in Winter Haven).
Jul 12 – 19
Home in Lake Alfred
4.95 out of 5 average rating, 41 reviewsCentral FL Bungalow! 2BR/1B With Fully Fenced Yard
Mar 5 – 12
Home in Winter Haven
4.95 out of 5 average rating, 85 reviews3/2 House w Heated Pool 5mins to Legoland
Oct 16 – 23
Home in Winter Haven
4.94 out of 5 average rating, 18 reviewsOverlook Joy
Aug 22 – 29
Home in Winter Haven
5.0 out of 5 average rating, 12 reviewsCozy Legoland Pool House
Aug 5 – 12
Home in Winter Haven
4.96 out of 5 average rating, 46 reviewsThe Family Friendly Fun House
Jan 14 – 21
Private house rentals
Home in Haines City
5.0 out of 5 average rating, 3 reviewsGolf Course Retreat
Jul 14 – 21
Home in Winter Haven
5.0 out of 5 average rating, 3 reviewsPeaceful Lakeside Escape
Sep 11 – 18
Home in Winter Haven
5.0 out of 5 average rating, 33 reviews341 Legoland Sherman's Antiques Lake Silver
May 11 – 18
Home in Davenport
4.93 out of 5 average rating, 60 reviewsSweet vacation home.
May 15 – 22
Home in Eagle Lake
4.82 out of 5 average rating, 17 reviewsQuaint Cottage. 6 mi to Legoland. Pet friendly!
Dec 14 – 21
Home in Winter Haven
4.87 out of 5 average rating, 30 reviewsCharming Town House
Sep 1 – 8
Home in Winter Haven
5.0 out of 5 average rating, 17 reviewsCozy on the Canal near Legoland
Oct 8 – 15
Home in Winter Haven
4.91 out of 5 average rating, 33 reviewsLake Front Lego Land Estate
May 3 – 10
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
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