Title: Winter Park Vacation Home Rentals from CA $197: Search Top Private Vacation Homes for Rent | Expedia.ca

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![Casa Feliz Historic Home Museum featuring a park and a house](https://images.trvl-media.com/place/6154784/fc715ff8-b152-4bf8-a1b6-c4214a58153a.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6154784/fc715ff8-b152-4bf8-a1b6-c4214a58153a.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winter Park vacation homes

![Property grounds](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/312f2783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/b34af36d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/7253cdd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/fc26e60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.ca/Orlando-Hotels-Charming-Home-Wp-Patio-Gazebo-Close-To-Highwys.h120187220.Hotel-Information)

CA $174

CA $365 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Orlando-Hotels-Charming-Home-Wp-Patio-Gazebo-Close-To-Highwys.h120187220.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/13f778dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/170acb69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/9e87b9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/18ad5479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Park

[](https://www.expedia.ca/Orlando-Hotels-Spacious-5-Bedroom-House-In-Gorgeous-Winter-Park.h121017283.Hotel-Information)

CA $234

CA $385 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Orlando-Hotels-Spacious-5-Bedroom-House-In-Gorgeous-Winter-Park.h121017283.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/fee1fbc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/64b5a908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/1bba5733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/3736e6a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in College Park

[](https://www.expedia.ca/Orlando-Hotels-Winter-Park-Gem.h118778200.Hotel-Information)

8.0/10

Very good

(2 reviews)

"We had a wonderful stay — the house was spotless, comfortable, and offered plenty of space. The peaceful neighborhood and convenient location made it easy to explore the area."

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

Danielle H.

CA $233

CA $528 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Orlando-Hotels-Winter-Park-Gem.h118778200.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/d9e95202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/8914dae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, computer monitors](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/a9d269d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/7061403d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.ca/Orlando-Hotels-Cozy-Home-5min-To-Park-Ave-And-Downtown-Orlando.h121857215.Hotel-Information)

CA $222

CA $406 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Orlando-Hotels-Cozy-Home-5min-To-Park-Ave-And-Downtown-Orlando.h121857215.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/w1350h895x0y5-06f55f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/a352947e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/36f4f2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/c29ed280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.ca/Orlando-Hotels-Funky-Remodeled-Otown-Bungalow-Sleeps-8.h123147976.Hotel-Information)

CA $220

CA $412 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Orlando-Hotels-Funky-Remodeled-Otown-Bungalow-Sleeps-8.h123147976.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/d0827223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/5d356775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/d7d75fc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/ea81348a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.ca/Orlando-Hotels-Mills-House-WP-Sleeps-11-Renovated-Queen-Beds.h119712429.Hotel-Information)

CA $230

CA $454 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Orlando-Hotels-Mills-House-WP-Sleeps-11-Renovated-Queen-Beds.h119712429.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/437efd0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/78c9ab55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/3aa946ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/0312eb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Park

[](https://www.expedia.ca/Orlando-Hotels-4-Bedroom-House-In-Superb-Winter-Park.h120488903.Hotel-Information)

4.0/10

(1 review)

"We checked in late and were surprised to find half eaten food in the fridge and freezer. Both were very dirty with a noticeable odor. The dishwasher was full of dirty dishes. The oven was full of dirty pans. Most of the dishes in the cupboards had little bits in them as well. There was a fire alarm battery beeping in one of the bedrooms. There was no coffee maker or wine opener or wine glasses or hand soap. There were very few dishes in general, it would have been challenging to cook and serve...

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

Nyssa S.

CA $368

CA $797 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Orlando-Hotels-4-Bedroom-House-In-Superb-Winter-Park.h120488903.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123820000/123810600/123810526/d5846256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/124000000/123820000/123810600/123810526/w1177h878x1y0-2d23bffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/124000000/123820000/123810600/123810526/025a39c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123820000/123810600/123810526/w1280h1255x0y4-267bfb8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kissimmee

[](https://www.expedia.ca/Orlando-Hotels-Charming-2-Bedroom-Florida-Getaway-Sleeps-6.h123810526.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Perfect! Place was clean. Parking was easy. ( Business travel)"

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

Matt S.

CA $83

CA $369 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Orlando-Hotels-Charming-2-Bedroom-Florida-Getaway-Sleeps-6.h123810526.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/90000000/89410000/89401800/89401769/c965de3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89410000/89401800/89401769/3ae1f54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89410000/89401800/89401769/479731f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/90000000/89410000/89401800/89401769/9507fd24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Union Park

[](https://www.expedia.ca/Orlando-Hotels-La-Casita-Pool-Oasis.h89401769.Hotel-Information)

9.8/10

Exceptional

(19 reviews)

"Great location , Very enjoy , private space, would book in the future for sure "

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

Matt B.

CA $153

CA $388 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Orlando-Hotels-La-Casita-Pool-Oasis.h89401769.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111190000/111183800/111183769/519e072c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111190000/111183800/111183769/eef64c45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111190000/111183800/111183769/e9a88111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/112000000/111190000/111183800/111183769/407b592c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Conway

[](https://www.expedia.ca/Orlando-Hotels-Lake-View-10min-To-Dwtn-Near-Parks-2-Guests.h111183769.Hotel-Information)

9.4/10

Exceptional

(3 reviews)

"Overall the stay was perfect!! Very cozy atmosphere with a great view of a lake. Super private area with lots of space to roam. Location was perfect, literally was close to everything. Very sad I had to cut my trip short but definitely would stay again. "

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

Freda T.

CA $63

CA $216 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Orlando-Hotels-Lake-View-10min-To-Dwtn-Near-Parks-2-Guests.h111183769.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110910000/110900200/110900191/6ea41fb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/111000000/110910000/110900200/110900191/ea640587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/111000000/110910000/110900200/110900191/a791c585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110910000/110900200/110900191/efdd09bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Azalea Park

[](https://www.expedia.ca/Orlando-Hotels-Private-Studio-Near-Parks-DNTN.h110900191.Hotel-Information)

9.0/10

Wonderful

(2 reviews)

CA $75

CA $236 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Orlando-Hotels-Private-Studio-Near-Parks-DNTN.h110900191.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/111000000/110800000/110795600/110795550/w2158h1438x0y0-8604c210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110800000/110795600/110795550/w2141h1428x0y1-40bd74dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110800000/110795600/110795550/w2143h1428x2y2-682f4b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110800000/110795600/110795550/w2142h1427x1y1-19dac4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Deltona

[](https://www.expedia.ca/Deltona-Hotels-Charming-2-Bedroom-House-With-WiFi.h110795550.Hotel-Information)

9.6/10

Exceptional

(11 reviews)

"Great stay! "

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

Ash L.

CA $109

CA $197 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Deltona-Hotels-Charming-2-Bedroom-House-With-WiFi.h110795550.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71730000/71725000/71724933/bd4fc8f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71730000/71725000/71724933/d783c6a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71730000/71725000/71724933/9b9db93f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71730000/71725000/71724933/e82049d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Buena Ventura Lakes

[](https://www.expedia.ca/Orlando-Hotels-Escape-To-ParadiseLuxury-Waterfront-Heated-Pool-House-In-Tranquil-Neighborhood.h71724933.Hotel-Information)

10/10

Exceptional

(22 reviews)

"Was a great property for our Disney vacation ! Very clean, nice beds . "

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

Ashley G.

CA $174

CA $433 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Orlando-Hotels-Escape-To-ParadiseLuxury-Waterfront-Heated-Pool-House-In-Tranquil-Neighborhood.h71724933.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83640000/83639200/83639104/1e5bbdee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83640000/83639200/83639104/c6e99f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83640000/83639200/83639104/f6d36493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/84000000/83640000/83639200/83639104/36587a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Orlando

[](https://www.expedia.ca/Orlando-Hotels-Tiny-Living-At-Large.h83639104.Hotel-Information)

9.0/10

Wonderful

(22 reviews)

"It was incredible! The tiny home feels incredibly cozy and was super easy to find. We had a wonderful visit."

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

Tristen H.

CA $89

CA $206 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Orlando-Hotels-Tiny-Living-At-Large.h83639104.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/34000000/33560000/33550500/33550485/3b8c2243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33560000/33550500/33550485/0897124c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/34000000/33560000/33550500/33550485/73c42aa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/34000000/33560000/33550500/33550485/0d3924ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kissimmee

[](https://www.expedia.ca/Orlando-Hotels-Breathtaking-Fantasy-World-Newly-Renovated-Near-Disney-22-5-Star-Unit.h33550485.Hotel-Information)

9.0/10

Wonderful

(115 reviews)

"Nice and relaxing. Great pool very within walking distance. Lots to do. Close to entertainment and shopping."

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

Beth R.

CA $96

CA $335 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Orlando-Hotels-Breathtaking-Fantasy-World-Newly-Renovated-Near-Disney-22-5-Star-Unit.h33550485.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93610000/93605100/93605011/e4e0c0bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/94000000/93610000/93605100/93605011/1ef7af6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93610000/93605100/93605011/69cd42cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/94000000/93610000/93605100/93605011/79c03dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sanford

[](https://www.expedia.ca/Sanford-Hotels-Home-Sweet-Home.h93605011.Hotel-Information)

9.6/10

Exceptional

(22 reviews)

"It was a great location for our trip and everything was true to the listing. The host was very responsive and helpful."

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

K B.

CA $126

CA $474 total

includes taxes & fees

Feb 9 - Feb 10

[](https://www.expedia.ca/Sanford-Hotels-Home-Sweet-Home.h93605011.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91270000/91263400/91263391/4b4bd432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91270000/91263400/91263391/898bd5e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91270000/91263400/91263391/9adcbfd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91270000/91263400/91263391/6c55d3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Wadeview Park

[](https://www.expedia.ca/Orlando-Hotels-Free-Laundry-Parking-Near-Downtown-Disney.h91263391.Hotel-Information)

10/10

Exceptional

(8 reviews)

"lovely!"

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

Abby B.

CA $152

CA $440 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Orlando-Hotels-Free-Laundry-Parking-Near-Downtown-Disney.h91263391.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90160000/90150800/90150726/w510h683x257y0-fb46a368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90160000/90150800/90150726/ca81d0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90160000/90150800/90150726/a7e04363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90160000/90150800/90150726/w822h683x101y0-5deb0938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Orlando

[](https://www.expedia.ca/Orlando-Hotels-Sunshine-Escape-Guesthouse.h90150726.Hotel-Information)

9.6/10

Exceptional

(12 reviews)

"The property was immaculately clean, stylish, roomy and private! It was so convenient to everything yet on the outskirts in a quiet peaceful neighborhood. "

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

KELLY Z.

CA $81

CA $236 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Orlando-Hotels-Sunshine-Escape-Guesthouse.h90150726.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99720000/99711400/99711337/d5efbbd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/100000000/99720000/99711400/99711337/cbcaf15a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/100000000/99720000/99711400/99711337/e59dd61a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99720000/99711400/99711337/d5c0d8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kissimmee

[](https://www.expedia.ca/Orlando-Hotels-DISNEY-AREA-RESORT-2-BEDROOM-VACATION-RENTAL-AWARD-WINNING-MILL-CREEK-RESORT.h99711337.Hotel-Information)

9.8/10

Exceptional

(14 reviews)

"The place was in a great community. We felt very safe and right at home. Very well maintained with so many things to do on property. Great communication from the property owner. You can’t go wrong booking a stay here! We will definitely be back!"

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

Emily D.

CA $124

CA $318 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Orlando-Hotels-DISNEY-AREA-RESORT-2-BEDROOM-VACATION-RENTAL-AWARD-WINNING-MILL-CREEK-RESORT.h99711337.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/58000000/57710000/57709100/57709079/w1125h1111x0y0-c0864400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/58000000/57710000/57709100/57709079/da548abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/58000000/57710000/57709100/57709079/w1125h844x0y796-563f5405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/58000000/57710000/57709100/57709079/aaf54c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Orlando

[](https://www.expedia.ca/Orlando-Hotels-Mi-Casa-Es-Su-Casa-4-Bdrm-Home-With-Pool.h57709079.Hotel-Information)

8.8/10

Excellent

(104 reviews)

"We had a great time at the house! Close to everything, spacious, clean, and with a good host! "

![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg)

Synnøve Sætervik H.

CA $157

CA $684 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Orlando-Hotels-Mi-Casa-Es-Su-Casa-4-Bdrm-Home-With-Pool.h57709079.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=2026-01-30&endDate=2026-01-31&regionId=7902&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=APART_HOTEL)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CHALET)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=HOUSE_BOAT)

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## Top Winter Park Hotel Reviews

![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg)

### Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"Room spotless, staff were amazing and very helpful. "

[](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information)

![Spark by Hilton Orlando near Universal](https://images.trvl-media.com/lodging/1000000/20000/16000/15927/5cf8836a_y.jpg)

### Spark by Hilton Orlando near Universal

10/10 Excellent

"The stay at Spark by Hilton Orlando near Universal was delightful. Upon entry into the hotel, I was warmly greeted by staff and was met with a tranquil environment. The room had an enchanting atmosphere, making my stay incredible."

[](https://expedia.ca/Orlando-Hotels-Spark-By-Hilton-Orlando-Near-Universal.h15927.Hotel-Information)

![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg)

### DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent

"Good "

[](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information)

![Hyatt Regency Orlando](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg)

### Hyatt Regency Orlando

10/10 Excellent

"Excellent"

[](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information)

![Ramada by Wyndham Suites Orlando Airport](https://images.trvl-media.com/lodging/1000000/130000/120400/120303/2eaf4a61_y.jpg)

### Ramada by Wyndham Suites Orlando Airport

10/10 Excellent

"Clean room, great amenities "

[](https://expedia.ca/Orlando-Hotels-Ramada-By-Wyndham-Suites-Orlando-Airport.h120303.Hotel-Information)

![Lake Buena Vista Resort Village & Spa](https://images.trvl-media.com/lodging/2000000/1360000/1350900/1350864/16b6b8e7_y.jpg)

### Lake Buena Vista Resort Village & Spa

10/10 Excellent

"Clean parking is a hassle but very. Clean "

[](https://expedia.ca/Orlando-Hotels-Lake-Buena-Vista-Resort-Village-Spa.h1350864.Hotel-Information)

![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg)

### DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Everything was amazing- the room, the staff the overall experience "

[](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information)

![Universal's Endless Summer Resort - Dockside Inn and Suites](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517_y.jpg)

### Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"Breakfast was not free."

[](https://expedia.ca/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information)

![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg)

### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Excellent and clean Resort, good location, spacious, easy to get around. Friendly staff. "

[](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information)

## Find out more about Winter Park

## Winter Park Vacation Homes information

| Number of reviews | 344                 |
| ----------------- | ------------------- |
| Accommodation     | 5892 Vacation Homes |
| Lowest Price      | CA $197             |
| Highest Price     | CA $797             |

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- [Albin Polasek Museum and Sculpture Gardens ](https://www.expedia.ca/Albin-Polasek-Museum-And-Sculpture-Gardens-Orlando.d6154778.Vacation-Attraction)
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- [Harry P. Leu Gardens ](https://www.expedia.ca/Harry-P-Leu-Gardens-Orlando.d6068689.Vacation-Attraction)
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- [Rollins Museum of Art ](https://www.expedia.ca/Rollins-Museum-Of-Art-Orlando.d6154782.Vacation-Attraction)
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- [Things to do in Orlando ](https://www.expedia.ca/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities)

- [Book Vacation Homes in Winter Park on Expedia.com ](https://www.expedia.com/Winter-Park-Private-Vacation-Homes.d7902-aaPrivateVacationHomes.Travel-Guide-Accommodation)