Title: Winter Park Vacation Rentals from CA $116: Short-Term Rentals for 2026 | Expedia.ca

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![Kraft Azalea Gardens showing a fountain, a park and a pond](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-06-12&endDate=2026-06-14&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 rentals

![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/3ef41108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/22001730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/55f38262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/a4a236a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1-bedroom vacation room just 12 minutes from University of Central Florida

[](https://www.expedia.ca/Orlando-Hotels-1-Bedroom-Vacation-Room-Just-12-Minutes-From-University-Of-Central-Florida.h91093651.Hotel-Information)

Orlando

9.4/10

Exceptional

(3 reviews)

"Fantastic Host"

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

Marek K.

CA $91

CA $244 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Orlando-Hotels-1-Bedroom-Vacation-Room-Just-12-Minutes-From-University-Of-Central-Florida.h91093651.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/180-b531af67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/b4b96d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/57a8906a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/081e1921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet and safe neighborhood come to this great place with lots of room for relax

[](https://www.expedia.ca/Orlando-Hotels-Quiet-And-Safe-Neighborhood-Come-To-This-Great-Place-With-Lots-Of-Room-For-Relax.h120648509.Hotel-Information)

Orlando

10/10

Exceptional

(1 review)

"Pool is very inviting"

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

Geri Lamborn M.

CA $160

CA $374 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Orlando-Hotels-Quiet-And-Safe-Neighborhood-Come-To-This-Great-Place-With-Lots-Of-Room-For-Relax.h120648509.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/4a4f7206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/4c2b0b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/c94baf8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/d34ef452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Boutique Guest house in Winter Park 

[](https://www.expedia.ca/Orlando-Hotels-Newly-Built-Stylish-Guest-House-With-Free-Parking.h78004694.Hotel-Information)

Winter Park

10/10

Exceptional

(103 reviews)

"Beautiful house and such sweet hosts! Would highly recommend! The cabinets were well stocked! "

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

Amber V.

CA $205

CA $474 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Orlando-Hotels-Newly-Built-Stylish-Guest-House-With-Free-Parking.h78004694.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)

![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)

![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)

### Cozy home 5min to Park Ave and Downtown Orlando

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

Fairview Shores

CA $266

CA $468 total

includes taxes & fees

Mar 15 - Mar 16

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/4e7b5cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/ad8a3de4.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/122000000/121830000/121826500/121826401/e47ef39a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/fb43e8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek, Spacious & Central – Your Ideal Getaway

[](https://www.expedia.ca/Orlando-Hotels-Sleek.h121826401.Hotel-Information)

Fairview Shores

10/10

Exceptional

(1 review)

"Great location in Winter Park! So many quality restaurants and things to do close by. The home is easily accessible with plenty of space. The host, Wendy was very hospitable. We left a toiletry bag and she was kind enough to let us know so we could come back. We enjoyed our one night stay!"

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

Adam A.

CA $165

CA $301 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Orlando-Hotels-Sleek.h121826401.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/1a1d4665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/eacfcee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/9a1d28f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/bf1a7baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Virbo Host Website is not working for me. Do not book this property. Thank you

[](https://www.expedia.ca/Orlando-Hotels-Money-Saving-Clean-Small-11-Private-Apartment-On-The-Orlando-Border.h121551588.Hotel-Information)

Fairview Shores

CA $74

CA $148 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Orlando-Hotels-Money-Saving-Clean-Small-11-Private-Apartment-On-The-Orlando-Border.h121551588.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)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/9dff99a8.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)

### Cozy home w/full kitchen & workspace

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

College Park

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 $107

CA $358 total

includes taxes & fees

Feb 25 - Feb 26

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

![Property grounds](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/312f2783.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/121000000/120190000/120187300/120187220/7335419c.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)

### Charming home @wp. Patio +Gazebo. close to highwys

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

Fairview Shores

10/10

Exceptional

(1 review)

"Very clean and location was great"

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

Vicki V.

CA $170

CA $357 total

includes taxes & fees

Feb 22 - Feb 23

[](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)

![Exterior](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/7f29b0af.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)

### Spacious 5-bedroom house in gorgeous Winter Park

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

Winter Park

CA $296

CA $459 total

includes taxes & fees

Feb 24 - Feb 25

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

![Smart TV, video games](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/4737a68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/c75613db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/c4b6e35a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/777ceefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

[](https://www.expedia.ca/Orlando-Hotels-Serene-Mid-Century-32-WBonus-Room-And-Huge-Shaded-Yard-WFence.h91693626.Hotel-Information)

Goldenrod

CA $252

CA $596 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Orlando-Hotels-Serene-Mid-Century-32-WBonus-Room-And-Huge-Shaded-Yard-WFence.h91693626.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)

![Interior](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/aeff95b3.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)

### Funky Remodeled Otown Bungalow Sleeps 8

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

Fairview Shores

CA $212

CA $398 total

includes taxes & fees

Feb 23 - Feb 24

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

![Pool](https://images.trvl-media.com/lodging/123000000/122300000/122291600/122291511/2eccd419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122300000/122291600/122291511/25a3e347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122300000/122291600/122291511/w1320h753x0y0-6ab2b54f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122300000/122291600/122291511/0a1ee9ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy RV with AC and fitness room in brilliant Winter Park

[](https://www.expedia.ca/Orlando-Hotels-Cozy-RV-With-AC-And-Fitness-Room-In-Brilliant-Winter-Park.h122291511.Hotel-Information)

Goldenrod

CA $181

CA $230 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Orlando-Hotels-Cozy-RV-With-AC-And-Fitness-Room-In-Brilliant-Winter-Park.h122291511.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/w1350h895x0y5-04b0130a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/f1476d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/9bd56f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/6de8c24e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfy Tiny Home @WP. Large Private Deck+Queen bed

[](https://www.expedia.ca/Orlando-Hotels-Comfy-Tiny-Home-WP-Large-Private-DeckQueen-Bed.h123398794.Hotel-Information)

Fairview Shores

CA $218

CA $360 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Orlando-Hotels-Comfy-Tiny-Home-WP-Large-Private-DeckQueen-Bed.h123398794.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)

![Interior](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/d7d75fc8.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)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/b29eebc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mills House @WP. Sleeps 11 Renovated. Queen beds

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

Fairview Shores

6.0/10

(1 review)

"The air fresheners plug ins were too powerful, we had to put them outside while we stayed in the house. Not enough power outlets. Hanging lamps on master bedroom are not practical, didn’t find the switch to turn them off. Spot light outside kept me up. The motion triggered the light to go on and off constantly. "

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

Monica E.

CA $234

CA $456 total

includes taxes & fees

Feb 23 - Feb 24

[](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)

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

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/b9965092.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)

### Cute 5-bedroom,6bed house in superb Winter Park.

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

Winter Park

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 $436

CA $877 total

includes taxes & fees

Feb 24 - Feb 25

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

![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)

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

![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/90000000/89410000/89401800/89401769/a650b2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious & Private Guest Pool House Oasis

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

Union Park

9.8/10

Exceptional

(21 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 $150

CA $377 total

includes taxes & fees

Mar 10 - Mar 11

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

![2 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/99000000/98470000/98469800/98469736/w4027h3010x5y0-555f91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment](https://images.trvl-media.com/lodging/99000000/98470000/98469800/98469736/1d758b0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/99000000/98470000/98469800/98469736/bd0a898d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch LCD TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/99000000/98470000/98469800/98469736/e7607662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Front Porch

[](https://www.expedia.ca/Sanford-Hotels-212-W-4th-St.h98469736.Hotel-Information)

Sanford

9.4/10

Exceptional

(3 reviews)

"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "

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

Johnny

[](https://www.expedia.ca/Sanford-Hotels-212-W-4th-St.h98469736.Hotel-Information)

![Standard Apartment | Living area](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/w4033h3016x0y6-00b73534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | Private kitchen](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/6e8626f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/d76725c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/e1a32506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Blue Aztec

[](https://www.expedia.ca/Sanford-Hotels-The-Blue-Aztec.h99354524.Hotel-Information)

Sanford

9.6/10

Exceptional

(13 reviews)

"Great location! Great Dining! "

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

Lisa

[](https://www.expedia.ca/Sanford-Hotels-The-Blue-Aztec.h99354524.Hotel-Information)

![Standard Apartment | Living area](https://images.trvl-media.com/lodging/100000000/99360000/99353800/99353747/216905b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | Living area](https://images.trvl-media.com/lodging/100000000/99360000/99353800/99353747/w4032h3012x0y7-d90d4baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99360000/99353800/99353747/c09dd838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment](https://images.trvl-media.com/lodging/100000000/99360000/99353800/99353747/8bf6b7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boho Nights

[](https://www.expedia.ca/Sanford-Hotels-Boho-Nights.h99353747.Hotel-Information)

Sanford

9.2/10

Wonderful

(10 reviews)

"Wonderful spot, and excellent hosts!"

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

Thomas

[](https://www.expedia.ca/Sanford-Hotels-Boho-Nights.h99353747.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/100000000/99880000/99871700/99871637/aab8aa70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/100000000/99880000/99871700/99871637/32eef9f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99880000/99871700/99871637/f2750c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/100000000/99880000/99871700/99871637/1ed742e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Private Apartment - Stylish & Spotless — No sharing areas 

[](https://www.expedia.ca/Orlando-Hotels-Cozy-Private-Apartment-Stylish-Spotless-No-Sharing-Areas.h99871637.Hotel-Information)

Orlando

10/10

Exceptional

(29 reviews)

"Mercedes is an amazing host and has thought of - and provided EVERYTHING you need for a fantastic stay. Would ABSOLUTELY stay here again and HIGHLY recommend!!"

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

Rick K.

CA $116

CA $250 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Orlando-Hotels-Cozy-Private-Apartment-Stylish-Spotless-No-Sharing-Areas.h99871637.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=2026-03-03&endDate=2026-03-04&regionId=7902&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_7902)

## 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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=HOUSE_BOAT)

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

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## Top Winter Park Hotel Reviews

![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

"All the above. Great staff and clean rooms. "

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

![La Quinta Inn & Suites by Wyndham Orlando Airport North](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/4fbafd8c_y.jpg)

### La Quinta Inn & Suites by Wyndham Orlando Airport North

10/10 Excellent

"Amazing, great service."

[](https://expedia.ca/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.Hotel-Information)

![Hyatt Regency Orlando International Airport](https://images.trvl-media.com/lodging/1000000/10000/2800/2754/acaa1e8b_y.jpg)

### Hyatt Regency Orlando International Airport

10/10 Excellent

"Check in was quick even with a line and room was very nice. Zero complaints."

[](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando-International-Airport.h2754.Hotel-Information)

![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg)

### Universal's Cabana Bay Beach Resort

10/10 Excellent

"Clean room, great food choices and friendly staff at check in."

[](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information)

![Rosen Inn Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg)

### Rosen Inn Lake Buena Vista

10/10 Excellent

"Nice room, nice staff, nice place"

[](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information)

![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg)

### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"Spotless room. Beautiful view. Nice staff and amenities. Will definitely be booking again"

[](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information)

![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg)

### Rosen Inn at Pointe Orlando

10/10 Excellent

"Room was clean "

[](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information)

![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/033f2fa5_y.jpg)

### Caribe Royale Orlando

10/10 Excellent

"Clean room, housekeeping and amenities were excellent!"

[](https://expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information)

![Marriott's Grande Vista](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg)

### Marriott's Grande Vista

10/10 Excellent

"Amenities. "

[](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information)

## Find out more about Winter Park

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 Park. 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.   

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- [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 Park ](https://expedia.ca/Winter-Park-Private-Vacation-Homes.d7902-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Winter Park ](https://expedia.ca/Winter-Park-Condos.d7902-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Winter Park ](https://expedia.ca/Winter-Park-Apartments.d7902-aaApartments.Travel-Guide-Accommodation)
- [Villas in Winter Park ](https://expedia.ca/Winter-Park-Villas.d7902-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Winter Park ](https://expedia.ca/Winter-Park-Resort-Hotels.d7902-aaResortHotels.Travel-Guide-Accommodation)
- [Cottages in Winter Park ](https://expedia.ca/Winter-Park-Cottages.d7902-aaCottages.Travel-Guide-Accommodation)
- [Aparthotels in Winter Park ](https://expedia.ca/Winter-Park-Apart-Hotels.d7902-aaApartHotels.Travel-Guide-Accommodation)
- [Townhomes in Winter Park ](https://expedia.ca/Winter-Park-Townhomes.d7902-aaTownhomes.Travel-Guide-Accommodation)
- [Guest Houses in Winter Park ](https://expedia.ca/Winter-Park-Guest-Houses.d7902-aaGuestHouses.Travel-Guide-Accommodation)
- [B&B in Winter Park ](https://expedia.ca/Winter-Park-Bed-And-Breakfast.d7902-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Winter Park ](https://expedia.ca/Winter-Park-Chalets.d7902-aaChalets.Travel-Guide-Accommodation)
- [Motels in Winter Park ](https://expedia.ca/Winter-Park-Motels.d7902-aaMotels.Travel-Guide-Accommodation)
- [Condo Resorts in Winter Park ](https://expedia.ca/Winter-Park-Condominium-Resort.d7902-aaCondominiumResort.Travel-Guide-Accommodation)
- [Houseboats in Winter Park ](https://expedia.ca/Winter-Park-Houseboats.d7902-aaHouseboats.Travel-Guide-Accommodation)
- [Farmstay in Winter Park ](https://expedia.ca/Winter-Park-Agritourism.d7902-aaAgritourism.Travel-Guide-Accommodation)
- [Lodges in Winter Park ](https://expedia.ca/Winter-Park-Lodges.d7902-aaLodges.Travel-Guide-Accommodation)
- [Cabin Rentals in Winter Park ](https://expedia.ca/Winter-Park-Cabins.d7902-aaCabins.Travel-Guide-Accommodation)
- [Residences in Winter Park ](https://expedia.ca/Winter-Park-Residences.d7902-aaResidences.Travel-Guide-Accommodation)
- [Hostels in Winter Park ](https://expedia.ca/Winter-Park-Hostels.d7902-aaHostels.Travel-Guide-Accommodation)
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- [Castles in Winter Park ](https://expedia.ca/Winter-Park-Castles.d7902-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

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- [Best Hotels in Kissimmee](https://expedia.ca/Kissimmee-Hotels.d7927.Travel-Guide-Hotels)
- [Best Hotels in Fern Park](https://expedia.ca/Fern-Park-Hotels.d7377.Travel-Guide-Hotels)
- [Four Seasons Hotels in Lake Buena Vista](https://expedia.ca/Lake-Buena-Vista-Hotels-Four-Seasons.0-0-d10870--bFourSeasons.Travel-Guide-Filter-Hotels)
- [Windermere Boutique Hotels](https://expedia.ca/Windermere-Hotels-Boutique-Hotel.0-0-d6085091-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Kissimmee Pet-friendly Hotels](https://expedia.ca/Kissimmee-Hotels-Pet-Friendly-Hotel.0-0-d7927-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Kissimmee Hotels with a Lazy River](https://expedia.ca/Kissimmee-Hotels-Hotels-With-A-Lazy-River.0-0-d7927-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels)
- [Kissimmee Cheap Hotels](https://expedia.ca/Kissimmee-Hotels-Cheap-Hotels.0-0-d7927-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Kissimmee Waterpark Hotels](https://expedia.ca/Kissimmee-Hotels-Waterpark-Hotels.0-0-d7927-tWaterparkHotels.Travel-Guide-Filter-Hotels)
- [Hotels with Early Check-in in Lake Buena Vista](https://expedia.ca/Lake-Buena-Vista-Hotels-Hotel-With-Early-Check-In.0-0-d10870-thotelwithearlycheckin.Travel-Guide-Filter-Hotels)
- [Best Hotels in Lake Buena Vista](https://expedia.ca/Lake-Buena-Vista-Hotels.d10870.Travel-Guide-Hotels)
- [Best Hotels in Celebration](https://expedia.ca/Celebration-Hotels.d602896.Travel-Guide-Hotels)
- [Kissimmee Hotels with Kitchenettes](https://expedia.ca/Kissimmee-Hotels-Hotels-With-Kitchenettes.0-0-d7927-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels)
- [Lake Buena Vista Pet-friendly Hotels](https://expedia.ca/Lake-Buena-Vista-Hotels-Pet-Friendly-Hotel.0-0-d10870-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Wyndham Extra Holidays Hotels in Lake Buena Vista](https://expedia.ca/Lake-Buena-Vista-Hotels-Wyndham-Extra-Holidays.0-0-d10870--bWyndhamExtraHolidays.Travel-Guide-Filter-Hotels)
- [Fern Park Spa Hotels](https://expedia.ca/Fern-Park-Hotels-Spa-Hotel.0-0-d7377-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Wyndham Extra Holidays Hotels in Celebration](https://expedia.ca/Celebration-Hotels-Wyndham-Extra-Holidays.0-0-d602896--bWyndhamExtraHolidays.Travel-Guide-Filter-Hotels)
- [Kissimmee All Inclusive Resorts and Hotels](https://expedia.ca/Kissimmee-Hotels-All-Inclusive-Hotel.0-0-d7927-tAllInclusiveHotel.Travel-Guide-Filter-Hotels)

Flights

- [Flights to ORL](https://expedia.ca/Cheap-Flights-To-Kissimmee.d7927.Travel-Guide-Flights)

Cars

- [Car rentals in Kissimmee](https://expedia.ca/Car-Rentals-In-Kissimmee.d7927.Car-Rental-Guide)
- [Car rentals in Lake Buena Vista](https://expedia.ca/Car-Rentals-In-Lake-Buena-Vista.d10870.Car-Rental-Guide)

Activities

- [Things to do in Celebration](https://expedia.ca/Things-To-Do-In-Celebration.d602896.Travel-Guide-Activities)
- [Things to do in Lake Buena Vista](https://expedia.ca/Things-To-Do-In-Lake-Buena-Vista.d10870.Travel-Guide-Activities)
- [Things to do in Kissimmee](https://expedia.ca/Things-To-Do-In-Kissimmee.d7927.Travel-Guide-Activities)

Packages

- [Kissimmee Holidays](https://expedia.ca/Kissimmee.d7927.Destination-Travel-Guides)

Vacation Rentals

- [Vacation Rental Lake Buena Vista](https://expedia.ca/Lake-Buena-Vista-Vacation-Rentals.d10870.Travel-Guide-VacationRentals)
- [Vacation Rental Kissimmee](https://expedia.ca/Kissimmee-Vacation-Rentals.d7927.Travel-Guide-VacationRentals)
- [Vacation Rental Celebration](https://expedia.ca/Celebration-Vacation-Rentals.d602896.Travel-Guide-VacationRentals)

General

- [Visit Altamonte Springs](https://expedia.ca/Altamonte-Springs.dx5965)
- [Visit Celebration](https://expedia.ca/Celebration.dx602896)
- [Visit Kissimmee](https://expedia.ca/Kissimmee.dx7927)

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