House vacation rentals in Winter Haven
Find and book unique houses on Airbnb
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 Auburndale
4.94 out of 5 average rating, 146 reviewsLake Whistler Beach House with lakefront pool
Aug 16 – 23
Home in Davenport
4.95 out of 5 average rating, 161 reviewsDOLPHIN COVE NEAR DISNEY
Jan 22 – 29
Home in Lakeland
4.86 out of 5 average rating, 109 reviewsHollingsworth Pool Home
Nov 15 – 22
Home in Davenport
4.8 out of 5 average rating, 137 reviewsKing bed pool in 4 corners area near shopping
Aug 30 – Sep 6
Home in Davenport
4.98 out of 5 average rating, 104 reviewsSunset Villa
Aug 29 – Sep 5
Home in Davenport
4.87 out of 5 average rating, 122 reviewsDisney getaway
Sep 24 – Oct 1
Home in Haines City
4.95 out of 5 average rating, 140 reviewsLuxury Home 4/3 near Disney, 2 Masters
Apr 29 – May 6
Home in Haines City
4.82 out of 5 average rating, 107 reviewsSouthern Dunes Golf Vacation Villa
Dec 20 – 27
Weekly house rentals
Home in Winter Haven
4.94 out of 5 average rating, 17 reviewsKid-friendly Home w/ Pool & BBQ
Oct 30 – Nov 6
Home in Winter Haven
4.84 out of 5 average rating, 19 reviewsElohim Guest House (Cozy House in Winter Haven).
Aug 1 – 8
Home in Winter Haven
5.0 out of 5 average rating, 11 reviewsCozy Lakefront Home w/ Pool -7 mins from Legoland
Oct 14 – 21
Home in Winter Haven
4.93 out of 5 average rating, 15 reviewsA charming lake house 4 beds/2ba
Sep 18 – 25
Home in Winter Haven
4.94 out of 5 average rating, 18 reviewsOverlook Joy
Sep 4 – 11
Home in Winter Haven
4.95 out of 5 average rating, 85 reviews3/2 House w Heated Pool 5mins to Legoland
Jun 24 – Jul 1
Home in Winter Haven
4.96 out of 5 average rating, 47 reviewsThe Family Friendly Fun House
Jan 5 – 12
Home in Lake Wales
4.97 out of 5 average rating, 29 reviewsLa Casita Redonda
Sep 16 – 23
Private house rentals
Home in Haines City
5.0 out of 5 average rating, 4 reviewsGolf Course Retreat
Sep 5 – 12
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
4.98 out of 5 average rating, 59 reviewsLake View, Game Room, 10 min Legoland
Mar 23 – 30
Home in Lakeland
4.99 out of 5 average rating, 99 reviewsSwan Studio Lakeland
Oct 29 – Nov 5
Home in Winter Haven
4.89 out of 5 average rating, 53 reviews3-br peaceful home near Legoland
Apr 21 – 28
Home in Winter Haven
5.0 out of 5 average rating, 33 reviews341 Legoland Sherman's Antiques Lake Silver
Jun 13 – 20
Home in Winter Haven
4.91 out of 5 average rating, 33 reviewsLake Front Lego Land Estate
Oct 15 – 22
Home in Lake Wales
5.0 out of 5 average rating, 45 reviewsLake access, Canal front Crooked Lake Gem
Jun 26 – Jul 3
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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