Holiday 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.
Holiday 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
26 Apr – 3 May
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, 122 reviewsDisney getaway
25 Oct – 1 Nov
Home in Winter Haven
4.95 out of 5 average rating, 84 reviews3/2 House w Heated Pool 5mins to Legoland
27 Jun – 4 Jul
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 Davenport
4.93 out of 5 average rating, 60 reviewsSweet vacation home.
15–22 May
Condo rentals with a pool
Condo in Davenport
4.84 out of 5 average rating, 141 reviewsFull Service Gated Resort, Close to Disney & MCO!
8–15 Sep
Condo in Davenport
4.91 out of 5 average rating, 211 reviews3/2 King Bed Apartment near Disney Universal
17–24 Nov
Condo in Davenport
4.92 out of 5 average rating, 377 reviewsMediterranean Resort! 2+2 Condo. 10 mins to Disney
9–16 Nov
Condo in Davenport
4.94 out of 5 average rating, 135 reviewsIsland Style at Bahama Bay - Minutes to Disney!
8–15 Sep
Condo in Four Corners
4.86 out of 5 average rating, 107 reviews"Ocean's Gate" - 2BD/2BA condo near Disney
4–11 Dec
Condo in Davenport
4.97 out of 5 average rating, 152 reviewsDisney Orlando Bahama Bay Resort Theme Parks &More
30 Nov – 7 Dec
Condo in Kissimmee
4.98 out of 5 average rating, 290 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
21–28 Nov
Condo in Davenport
4.91 out of 5 average rating, 159 reviewsThe Smuggler's Gateway
21–28 Jul
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
4–11 Sep
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
30 Jan – 6 Feb
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
24–31 Aug
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
11–18 Jan
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
4–11 Oct
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
3–10 Dec
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
25 Jun – 2 Jul
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
6–13 Dec
Quick stats about holiday rentals with a pool in Winter Haven
Total rentals
80 properties
Wi-Fi availability
80 properties include access to Wi-Fi
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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