Title: Winter Haven Vacation Rentals from CA $171: Short-Term Rentals for 2026 | Expedia.ca

[Winter Haven Travel Guide](https://expedia.ca/Winter-Haven.dx7464)[Hotels in Winter Haven](https://expedia.ca/Winter-Haven-Hotels.d7464.Travel-Guide-Hotels)[Flights to Winter Haven](https://expedia.ca/Cheap-Flights-To-Winter-Haven.d7464.Travel-Guide-Flights)[Things to do in Winter Haven](https://expedia.ca/Things-To-Do-In-Winter-Haven.d7464.Travel-Guide-Activities)[Winter Haven Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Haven.d7464.Car-Rental-Guide)[Winter Haven Vacation Packages](https://expedia.ca/Winter-Haven.d7464.Destination-Travel-Guides)

![Winter Haven showing rides](https://images.trvl-media.com/place/7464/a00f555f-1771-4135-ad57-834cb1a10a56.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Winter Haven Vacation Rentals

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## Check prices for these dates

Tonight

[Dec 7 - Dec 8](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-07&endDate=2025-12-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 8 - Dec 9](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-08&endDate=2025-12-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7464&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Winter Haven

![Aerial view](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/fb6985f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/63e7fb0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hiking](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/9e1fc450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068973/41323424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Kissimmee

8.6/10

Excellent

(3087)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jose

CA $121

CA $172 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Vacation-Village-At-Parkway.h1068973.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/23050871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/f3c73455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/8bc597c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/28000000/27550000/27548600/27548551/26d508b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

8.8/10

Excellent

(1742)

"Amazing accommodations "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Marina

CA $261

CA $573 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando-Cottages-By-Rentyl.h27548551.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/c7c5e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/93c8e502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 4 Bedrooms (2 King, 1 Queen, & 2 Trundle Bed) | Balcony view](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/c3a6b674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695932/4a4db2cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kissimmee

9.6/10

Exceptional

(1999)

"Recommended amazing stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elf

CA $170

CA $207 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Orlando-Hotels-The-Berkley.h1695932.Hotel-Information)

![Billiards](https://images.trvl-media.com/lodging/2000000/1840000/1838800/1838783/cab10b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/2000000/1840000/1838800/1838783/71d234b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1840000/1838800/1838783/67dca9c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1840000/1838800/1838783/2dc39584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo resort in Kissimmee

8.4/10

Very good

(3019)

" Clean room and a great staff"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Victor

CA $173

CA $469 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-CLC-Regal-Oaks-Resort-Vacation-Townhomes.h1838783.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111410000/111401500/111401427/a1409b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's play area - outdoor](https://images.trvl-media.com/lodging/112000000/111410000/111401500/111401427/0a0c9635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/112000000/111410000/111401500/111401427/79f73889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/112000000/111410000/111401500/111401427/5681a60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

9.0/10

Wonderful

(165)

"Fully equipped kitchen was decent, staff was warm and welcoming."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karunya Bharadwaja

CA $136

CA $172 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Orlando-Hotels-Barefootn-Resort.h111401427.Hotel-Information)

![Water park](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/45af642e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/0666884a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![ONE BEDROOM GRANDE SUITE | Private kitchen](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/e96914e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/1000000/992500/992499/cbe2f6c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Reunion

8.8/10

Excellent

(1436)

"Family Friendly"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Janaya

CA $323

CA $432 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Reunion-Resort-Golf-Club.h992499.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/10000000/9050000/9046300/9046290/8e0b9435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/10000000/9050000/9046300/9046290/02d9bf29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9050000/9046300/9046290/b008f649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Villa, 3 Bedrooms, Non Smoking, Pool View (2 Floors)](https://images.trvl-media.com/lodging/10000000/9050000/9046300/9046290/aac68c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

9.2/10

Wonderful

(1153)

"Fully equipped kitchen, clean bathrooms"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shahid

[](https://www.expedia.ca/Orlando-Hotels-Magic-Village-Yards.h9046290.Hotel-Information)

![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/5000000/4660000/4651300/4651255/2fcd2016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Townhome, 4 Bedrooms, Private Pool | Living area](https://images.trvl-media.com/lodging/5000000/4660000/4651300/4651255/623713dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Townhome, 4 Bedrooms, Private Pool | Living area](https://images.trvl-media.com/lodging/5000000/4660000/4651300/4651255/e651e5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/5000000/4660000/4651300/4651255/b0f8f739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

8.4/10

Very good

(1400)

"2nd time staying here safe to say this is our second home "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melanie

CA $129

CA $419 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Orlando-Hotels-CLC-Encantada-Resort-Vacation-Townhomes.h4651255.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/119000000/118680000/118679700/118679692/5254aadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/119000000/118680000/118679700/118679692/d67d1f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118680000/118679700/118679692/fa9c1d63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118680000/118679700/118679692/71a6f0d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

7.0/10

Good

(4)

"Parking can be an issue but as long as you communicate with the others, you’ll be alright. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shana

CA $77

CA $182 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Magical-Dreams.h118679692.Hotel-Information)

![2 outdoor pools, open 8 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/600000/597200/597113/027f136a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/600000/597200/597113/2909eab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 3 Bedrooms (Lodge) | Private kitchen](https://images.trvl-media.com/lodging/1000000/600000/597200/597113/b4b69417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/600000/597200/597113/c50e45b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Davenport

9.2/10

Wonderful

(499)

"Everything was great "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bobby

CA $151

CA $193 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Orlando-Hotels-Holiday-Inn-Club-Vacations-Orlando-Breeze-Resort.h597113.Hotel-Information)

![Dock](https://images.trvl-media.com/lodging/38000000/37620000/37613200/37613141/6af08a1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/38000000/37620000/37613200/37613141/8b42a824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/38000000/37620000/37613200/37613141/d6c448ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/38000000/37620000/37613200/37613141/15a7f110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

9.2/10

Wonderful

(153)

"Amber was great we had a ball definitely coming back resort was beautiful "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

TAIYLAR

[](https://www.expedia.ca/Orlando-Hotels-The-Grand-Lake-Resort.h37613141.Hotel-Information)

![Private pool](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/9a3d3e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Townhome, 5 Bedrooms, Private Pool](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/74efd052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Townhome, 5 Bedrooms, Private Pool | Private kitchen](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/6699c829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Townhome, 5 Bedrooms, Private Pool | Living area](https://images.trvl-media.com/lodging/76000000/75970000/75962100/75962058/85d76152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kissimmee

9.4/10

Exceptional

(193)

"Loved our stay here. Would highly recommend "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Walter

CA $229

CA $701 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Formosa-Valley-Resort-By-UNE-Homes.h75962058.Hotel-Information)

![Dock](https://images.trvl-media.com/lodging/6000000/5290000/5287800/5287768/f1fc2176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/6000000/5290000/5287800/5287768/04ace0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/6000000/5290000/5287800/5287768/4a5f5c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/6000000/5290000/5287800/5287768/ec893e47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

9.0/10

Wonderful

(1796)

"Barefoot Suites is just an overall an awesome place to stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Loretta

[](https://www.expedia.ca/Orlando-Hotels-Barefoot-Suites.h5287768.Hotel-Information)

![Lake view](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068972/cacc5dfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068972/a57e1571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068972/68ec9286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/2000000/1070000/1069000/1068972/7e68d8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Kissimmee

9.4/10

Exceptional

(151)

"Very nice quiet place... very polite front desk personnel "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Iliana

[](https://www.expedia.ca/Orlando-Hotels-Lifetime-Of-Vacations-Resort.h1068972.Hotel-Information)

![Captiva-06 (SMV104) | Private kitchen](https://images.trvl-media.com/lodging/21000000/20240000/20231400/20231360/1cfa809e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Islamorada-01 (SMV102) | Shared kitchen](https://images.trvl-media.com/lodging/21000000/20240000/20231400/20231360/03cd9bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Captiva-11 (SMV116) | Private kitchen](https://images.trvl-media.com/lodging/21000000/20240000/20231400/20231360/514040a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/21000000/20240000/20231400/20231360/cfc0e773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kissimmee

8.4/10

Very good

(152)

"Not enough parking "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Corey

[](https://www.expedia.ca/Orlando-Hotels-Summerville-Vacation-Homes-By-Columbia-Management.h20231360.Hotel-Information)

![Sauna](https://images.trvl-media.com/lodging/120000000/119700000/119695700/119695623/4fa28cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Quadruple Room, 2 Queen Beds, Non Smoking, Private Bathroom](https://images.trvl-media.com/lodging/120000000/119700000/119695700/119695623/407a8e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119700000/119695700/119695623/ecab4876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, 1 Queen Bed, Non Smoking, Private Bathroom | Interior entrance](https://images.trvl-media.com/lodging/120000000/119700000/119695700/119695623/b28b75c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

CA $67

CA $171 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Harmony-Haven.h119695623.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/42000000/41900000/41898100/41898043/59585f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, foosball, stereo](https://images.trvl-media.com/lodging/42000000/41900000/41898100/41898043/2724dcb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/42000000/41900000/41898100/41898043/e26eb297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/42000000/41900000/41898100/41898043/2de67906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kissimmee

9.6/10

Exceptional

(48)

"Very nice property. The kids really enjoyed the themed rooms."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ahmed E.

[](https://www.expedia.ca/Orlando-Hotels-Glam-Villa-Near-The-Parks-W-Gamer-Princess-BRs.h41898043.Hotel-Information)

![Full-size fridge, microwave, cookware/dishes/utensils, freezer](https://images.trvl-media.com/lodging/120000000/119230000/119223100/119223033/w1529h1024x0y0-fc6b4550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/120000000/119230000/119223100/119223033/d71e5cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119230000/119223100/119223033/ba0b3e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/120000000/119230000/119223100/119223033/52b7f872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Solterra Resort

10/10

Exceptional

(1)

"Amazing "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nilda

CA $81

CA $184 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Jade-Manor.h119223033.Hotel-Information)

![Blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113250000/113245600/113245577/dc616ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private pool](https://images.trvl-media.com/lodging/114000000/113250000/113245600/113245577/9da06a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living room](https://images.trvl-media.com/lodging/114000000/113250000/113245600/113245577/268ce36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/114000000/113250000/113245600/113245577/44531f97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Davenport

9.4/10

Exceptional

(25)

"My family loved our stay highly recommend for family vacation. I would stay here again in the future!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Myia

CA $254

CA $618 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Doppio-Westside.h113245577.Hotel-Information)

![2 outdoor pools](https://images.trvl-media.com/lodging/112000000/111360000/111358100/111358085/f4f51507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment, Balcony | Private kitchen](https://images.trvl-media.com/lodging/112000000/111360000/111358100/111358085/6bd8d102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Apartment, Balcony | Living area](https://images.trvl-media.com/lodging/112000000/111360000/111358100/111358085/w1479h998x0y0-fe77f980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Apartment, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/112000000/111360000/111358100/111358085/d70dd7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Champions Gate

9.0/10

Wonderful

(52)

"Home and owners were amazing. We would definitely stay again if need. Great for soccer families as there is a little field right across the street. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melissa

CA $152

CA $424 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Orlando-Hotels-Champions-Gate-Condos-By-UNE.h111358085.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-22&endDate=2025-12-23&regionId=7464&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-03-07&d1=2026-03-07&endDate=2026-03-10&d2=2026-03-10&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-03-07&d1=2026-03-07&endDate=2026-03-10&d2=2026-03-10&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-03-07&d1=2026-03-07&endDate=2026-03-10&d2=2026-03-10&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-03-07&d1=2026-03-07&endDate=2026-03-10&d2=2026-03-10&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-03-07&d1=2026-03-07&endDate=2026-03-10&d2=2026-03-10&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-03-07&d1=2026-03-07&endDate=2026-03-10&d2=2026-03-10&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-03-07&d1=2026-03-07&endDate=2026-03-10&d2=2026-03-10&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Haven%2C+Florida%2C+United+States+of+America&regionId=7464&latLong=28.022253%2C-81.73286&adults=2&startDate=2026-03-07&d1=2026-03-07&endDate=2026-03-10&d2=2026-03-10&lodging=CHALET)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Haven-Vacation-Rentals.d7464.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Haven-Vacation-Rentals.d7464.Travel-Guide-VacationRentals)

## Top Winter Haven Hotel Reviews

![Silver Lake Resort](https://images.trvl-media.com/lodging/1000000/20000/14600/14518/f53cedc1_y.jpg)

### Silver Lake Resort

10/10 Excellent

"Room was clean and well stocked . Property was well maintained . "

[](https://expedia.ca/Orlando-Hotels-Silver-Lake-Resort.h14518.Hotel-Information)

![Margaritaville Resort Orlando](https://images.trvl-media.com/lodging/25000000/24060000/24054800/24054711/5f422c24_y.jpg)

### Margaritaville Resort Orlando

10/10 Excellent

"Great location, close to Disney, heated pool it was a big plus, Nice breakfast and service! "

[](https://expedia.ca/Orlando-Hotels-Margaritaville-Resort-Orlando.h24054711.Hotel-Information)

![The Grove Resort & Water Park Orlando](https://images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg)

### The Grove Resort & Water Park Orlando

10/10 Excellent

"One of the best resorts my family and I have ever been to! We had an amazing experience, very spacious, luxury-style service and accommodations. And the room was spotless…the cleanest room we’ve ever stayed in! The pool and water park 😍👌"

[](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information)

![Comfort Inn & Suites Kissimmee by the Parks](https://images.trvl-media.com/lodging/1000000/440000/430500/430452/578ae569_y.jpg)

### Comfort Inn & Suites Kissimmee by the Parks

10/10 Excellent

"Very nice"

[](https://expedia.ca/Orlando-Hotels-Comfort-Inn-Maingate.h430452.Hotel-Information)

![Ramada by Wyndham Kissimmee Gateway](https://images.trvl-media.com/lodging/1000000/50000/40600/40513/b94616ba_y.jpg)

### Ramada by Wyndham Kissimmee Gateway

10/10 Excellent

"Clean room, location, facilities "

[](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Kissimmee-Gateway.h40513.Hotel-Information)

![Holiday Inn Resort Kissimmee by the Parks by IHG](https://images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b_y.jpg)

### Holiday Inn Resort Kissimmee by the Parks by IHG

10/10 Excellent

"Nice location "

[](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information)

![Kompose Boutique Resort at Theme Parks](https://images.trvl-media.com/lodging/101000000/100840000/100837800/100837786/3cf09a4a_y.jpg)

### Kompose Boutique Resort at Theme Parks

10/10 Excellent

"Room was nice and clean. Real close by the Theme parks. Enjoyed the stay."

[](https://expedia.ca/Orlando-Hotels-Kompose-Boutique-Resort-At-Theme-Parks.h100837786.Hotel-Information)

![Parkway International Resort](https://images.trvl-media.com/lodging/1000000/700000/692700/692651/fd297cb8_y.jpg)

### Parkway International Resort

10/10 Excellent

"Room was great, staff friendly."

[](https://expedia.ca/Orlando-Hotels-Parkway-International-Resort.h692651.Hotel-Information)

![Staybridge Suites Orlando Royale Parc Suites by IHG](https://images.trvl-media.com/lodging/1000000/10000/7100/7008/a5ca763f_y.jpg)

### Staybridge Suites Orlando Royale Parc Suites by IHG

10/10 Excellent

"Great breakfast. Nice and quiet despite families."

[](https://expedia.ca/Orlando-Hotels-Staybridge-Suites-Orlando-Royale-Parc-Suites.h7008.Hotel-Information)

## Find out more about Winter Haven

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winter Haven. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

## Explore a world of travel with Expedia

- Trending destinations on Expedia.ca
- All accommodation types in Winter Haven

### Trending destinations on Expedia.ca

- [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals)
- [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
- [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals)
- [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals)
- [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals)
- [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals)
- [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations)
- [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals)
- [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals)
- [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals)
- [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals)
- [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals)
- [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals)
- [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals)
- [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals)
- [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
- [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
- [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Winter Haven ](https://expedia.ca/Winter-Haven-Private-Vacation-Homes.d7464-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Villas in Winter Haven ](https://expedia.ca/Winter-Haven-Villas.d7464-aaVillas.Travel-Guide-Accommodation)
- [Condo Rentals in Winter Haven ](https://expedia.ca/Winter-Haven-Condos.d7464-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Winter Haven ](https://expedia.ca/Winter-Haven-Apartments.d7464-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winter Haven ](https://expedia.ca/Winter-Haven-Cottages.d7464-aaCottages.Travel-Guide-Accommodation)
- [Resorts in Winter Haven ](https://expedia.ca/Winter-Haven-Resort-Hotels.d7464-aaResortHotels.Travel-Guide-Accommodation)
- [Townhomes in Winter Haven ](https://expedia.ca/Winter-Haven-Townhomes.d7464-aaTownhomes.Travel-Guide-Accommodation)
- [Aparthotels in Winter Haven ](https://expedia.ca/Winter-Haven-Apart-Hotels.d7464-aaApartHotels.Travel-Guide-Accommodation)
- [Guest Houses in Winter Haven ](https://expedia.ca/Winter-Haven-Guest-Houses.d7464-aaGuestHouses.Travel-Guide-Accommodation)
- [Motels in Winter Haven ](https://expedia.ca/Winter-Haven-Motels.d7464-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Winter Haven ](https://expedia.ca/Winter-Haven-Cabins.d7464-aaCabins.Travel-Guide-Accommodation)
- [B&B in Winter Haven ](https://expedia.ca/Winter-Haven-Bed-And-Breakfast.d7464-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Winter Haven ](https://expedia.ca/Winter-Haven-Chalets.d7464-aaChalets.Travel-Guide-Accommodation)
- [Residences in Winter Haven ](https://expedia.ca/Winter-Haven-Residences.d7464-aaResidences.Travel-Guide-Accommodation)
- [Condo Resorts in Winter Haven ](https://expedia.ca/Winter-Haven-Condominium-Resort.d7464-aaCondominiumResort.Travel-Guide-Accommodation)
- [Houseboats in Winter Haven ](https://expedia.ca/Winter-Haven-Houseboats.d7464-aaHouseboats.Travel-Guide-Accommodation)
- [Riads in Winter Haven ](https://expedia.ca/Winter-Haven-Riads.d7464-aaRiads.Travel-Guide-Accommodation)
- [Farmstay in Winter Haven ](https://expedia.ca/Winter-Haven-Agritourism.d7464-aaAgritourism.Travel-Guide-Accommodation)
- [RV Parks in Winter Haven ](https://expedia.ca/Winter-Haven-RV-Parks.d7464-aaRVParks.Travel-Guide-Accommodation)
- [Holiday Park Resorts in Winter Haven ](https://expedia.ca/Winter-Haven-Holiday-Parks.d7464-aaHolidayParks.Travel-Guide-Accommodation)
- [Lodges in Winter Haven ](https://expedia.ca/Winter-Haven-Lodges.d7464-aaLodges.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find a vacation rental in Winter Haven?

### What's the top vacation rental that Winter Haven has to offer?

### How many vacation rentals are there in Winter Haven?

### What can I see and do in Winter Haven?

### What are vacation rentals like in Winter Haven?

### Expedia's Latest Trends

Hotels

- [Hotels in Panama City Beach](https://expedia.ca/Panama-City-Beach-Hotels.d8021.Travel-Guide-Hotels)
- [Hotels in St. Augustine](https://expedia.ca/St-Augustine-Hotels.d6047864.Travel-Guide-Hotels)
- [Hotels in Key West](https://expedia.ca/Key-West-Hotels.d1187.Travel-Guide-Hotels)
- [Oceanfront Hotels in Cocoa Beach](https://expedia.ca/Cocoa-Beach-Hotels-Oceanfront-Hotels.0-0-d6549-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Beach Hotel in Siesta Key](https://expedia.ca/Siesta-Key-Hotels-Beach-Hotel.0-0-d6881-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Key Largo](https://expedia.ca/Key-Largo-Hotels.d8369.Travel-Guide-Hotels)
- [Hotels in Fort Myers Beach](https://expedia.ca/Fort-Myers-Beach-Hotels.d7194.Travel-Guide-Hotels)
- [All Inclusive Resorts and Hotels in Key West](https://expedia.ca/Key-West-Hotels-All-Inclusive-Hotel.0-0-d1187-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)
- [Hotels in Naples](https://expedia.ca/Naples-Hotels.d602724.Travel-Guide-Hotels)
- [Hotels in Daytona Beach](https://expedia.ca/Daytona-Beach-Hotels.d6023995.Travel-Guide-Hotels)
- [Hotels in Marco Island](https://expedia.ca/Marco-Island-Hotels.d8812.Travel-Guide-Hotels)
- [Hotels in West Palm Beach](https://expedia.ca/West-Palm-Beach-Hotels.d2742.Travel-Guide-Hotels)
- [Hotels in Fort Myers](https://expedia.ca/Fort-Myers-Hotels.d602729.Travel-Guide-Hotels)
- [Hotels in Sarasota](https://expedia.ca/Sarasota-Hotels.d602719.Travel-Guide-Hotels)

Flights

- [Cheap Flights to Sarasota](https://expedia.ca/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)
- [Cheap Flights to Naples](https://expedia.ca/Cheap-Flights-To-Naples.d602724.Travel-Guide-Flights)
- [Cheap Flights to Fort Myers](https://expedia.ca/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights)
- [Cheap Flights to Daytona Beach](https://expedia.ca/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights)
- [Cheap Flights to Punta Gorda](https://expedia.ca/Cheap-Flights-To-Punta-Gorda.d9394.Travel-Guide-Flights)
- [Cheap Flights to Cape Canaveral](https://expedia.ca/Cheap-Flights-To-Cape-Canaveral.d6484.Travel-Guide-Flights)
- [Cheap Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)

Cars

- [Car rentals in Fort Myers](https://expedia.ca/Car-Rentals-In-Fort-Myers.d602729.Car-Rental-Guide)

Activities

- [Things to do in Sarasota](https://expedia.ca/Things-To-Do-In-Sarasota.d602719.Travel-Guide-Activities)
- [Things to do in New Smyrna Beach](https://expedia.ca/Things-To-Do-In-New-Smyrna-Beach.d8943.Travel-Guide-Activities)
- [Things to do in Daytona Beach](https://expedia.ca/Things-To-Do-In-Daytona-Beach.d6023995.Travel-Guide-Activities)
- [Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)
- [Things to do in Cape Coral](https://expedia.ca/Things-To-Do-In-Cape-Coral.d6521.Travel-Guide-Activities)
- [Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)

Packages

- [Key West Vacations](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides)

General

- [Visit Cocoa Beach](https://expedia.ca/Cocoa-Beach.dx6549)

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app