Accommodation 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
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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
21 – 28 Apr
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
23 – 30 Apr
Home in Davenport
4.87 out of 5 average rating, 120 reviewsDisney getaway
17 – 24 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
4.95 out of 5 average rating, 59 reviewsSweet vacation home.
13 – 20 May
Home in Haines City
4.89 out of 5 average rating, 19 reviewsHermies House
20 – 27 Sept
Home in Winter Haven
4.96 out of 5 average rating, 46 reviewsThe Family Friendly Fun House
6 – 13 Jan
Condo rentals with a pool
Condo in Davenport
4.84 out of 5 average rating, 140 reviewsFull Service Gated Resort, Close to Disney & MCO!
8 – 15 Sept
Condo in Davenport
4.92 out of 5 average rating, 377 reviewsMediterranean Resort! 2+2 Condo. 10 mins to Disney
10 – 17 Dec
Condo in Davenport
4.91 out of 5 average rating, 209 reviews3/2 King Bed Apartment near Disney Universal
23 – 30 Mar
Condo in Davenport
4.9 out of 5 average rating, 128 reviewsPremium Tuscana Resort Condo - Minutes to Disney!
23 – 30 July
Condo in Davenport
4.81 out of 5 average rating, 226 reviewsw POOL 2BR Near Disney & ChampionsGate - Sleeps 6
23 – 30 Aug
Condo in Davenport
4.97 out of 5 average rating, 152 reviewsDisney Orlando Bahama Bay Resort Theme Parks &More
24 Nov – 1 Dec
Condo in Kissimmee
4.98 out of 5 average rating, 289 reviewsGorgeous❤️ Pool & Lake View Condo near Disney Parks
30 Aug – 6 Sept
Condo in Davenport
4.91 out of 5 average rating, 159 reviewsThe Smuggler's Gateway
21 – 28 July
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
5 – 12 Sept
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
19 – 26 June
Home in Davenport
4.97 out of 5 average rating, 97 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
22 – 29 Mar
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
23 – 30 Nov
Villa in Kissimmee
4.79 out of 5 average rating, 223 reviewsVisit Disney World from a Sunny Home with a Pool
9 – 16 Dec
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
20 – 27 May
Home in Davenport
4.61 out of 5 average rating, 23 reviewsSolterra Resort 7br Family Home Pool Near Disney
14 – 21 Mar
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
1 – 8 Aug
Quick stats about accommodation 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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