Vacation rentals with a pool in Winter Haven
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Haven
Guests agree: these homes with a pool 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 rentals with a pool
House rentals with a pool
Home in Davenport
4.95 out of 5 average rating, 161 reviewsDOLPHIN COVE NEAR DISNEY
Apr 21 – 28
Home in Davenport
4.98 out of 5 average rating, 104 reviewsSunset Villa
Sep 2 – 9
Home in Auburndale
4.94 out of 5 average rating, 146 reviewsLake Whistler Beach House with lakefront pool
Apr 23 – 30
Home in Davenport
4.87 out of 5 average rating, 120 reviewsDisney getaway
Jan 17 – 24
Home in Davenport
4.9 out of 5 average rating, 104 reviewsCharming Home near Disney with Private Heated Pool
Oct 31 – Nov 7
Home in Davenport
4.95 out of 5 average rating, 59 reviewsSweet vacation home.
May 13 – 20
Home in Haines City
4.89 out of 5 average rating, 19 reviewsHermies House
Sep 20 – 27
Home in Winter Haven
4.96 out of 5 average rating, 46 reviewsThe Family Friendly Fun House
Jan 6 – 13
Condo rentals with a pool
Condo in Davenport
4.84 out of 5 average rating, 140 reviewsFull Service Gated Resort, Close to Disney & MCO!
Sep 8 – 15
Condo in Davenport
4.92 out of 5 average rating, 377 reviewsMediterranean Resort! 2+2 Condo. 10 mins to Disney
Dec 10 – 17
Condo in Davenport
4.91 out of 5 average rating, 209 reviews3/2 King Bed Apartment near Disney Universal
Mar 23 – 30
Condo in Davenport
4.9 out of 5 average rating, 128 reviewsPremium Tuscana Resort Condo - Minutes to Disney!
Jul 23 – 30
Condo in Davenport
4.81 out of 5 average rating, 226 reviewsw POOL 2BR Near Disney & ChampionsGate - Sleeps 6
Aug 23 – 30
Condo in Davenport
4.97 out of 5 average rating, 152 reviewsDisney Orlando Bahama Bay Resort Theme Parks &More
Nov 24 – Dec 1
Condo in Kissimmee
4.98 out of 5 average rating, 289 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
Aug 30 – Sep 6
Condo in Davenport
4.91 out of 5 average rating, 158 reviewsThe Smuggler's Gateway
Jul 21 – 28
Home rentals with a private pool
Townhouse in Kissimmee
4.83 out of 5 average rating, 191 reviewsBeach House with Private Pool and Clubhouse near Disney
Sep 5 – 12
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Jun 19 – 26
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Mar 22 – 29
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Nov 23 – 30
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
Dec 9 – 16
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
May 20 – 27
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
Mar 14 – 21
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Aug 1 – 8
Quick stats about vacation rentals with a pool in Winter Haven
Total rentals
80 properties
Wifi availability
80 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.6K reviews
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