Title: Winter Park Vacation Rentals from $96: Search Short-Term Rentals | Expedia.com

[Winter Park Travel Guide](https://expedia.com/Winter-Park.dx7902)[Hotels in Winter Park](https://expedia.com/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Flights to Winter Park](https://expedia.com/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Things to do in Winter Park](https://expedia.com/Things-To-Do-In-Winter-Park.d7902.Travel-Guide-Activities)[Car Rentals in Winter Park](https://expedia.com/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.com/Winter-Park.d7902.Destination-Travel-Guides)

![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)

## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.com/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 two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-07-17&endDate=2026-07-19&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

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/4d10ef55.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.com/Orlando-Hotels-Quiet-And-Safe-Neighborhood-Come-To-This-Great-Place-With-Lots-Of-Room-For-Relax.h120648509.Hotel-Information)

Orlando

10/10

Exceptional

(2 reviews)

"Pool is very inviting"

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

Geri Lamborn M.

$248 nightly

$276 total

Apr 21 - Apr 22

Total with taxes and fees

[](https://www.expedia.com/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/122000000/121830000/121826500/121826401/4e7b5cb0.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)

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

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

[](https://www.expedia.com/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.

$196 nightly

$218 total

Mar 30 - Mar 31

Total with taxes and fees

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

![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)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/71fcc6a8.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.com/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.

$154 nightly

$170 total

Apr 21 - Apr 22

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-1-Bedroom-Vacation-Room-Just-12-Minutes-From-University-Of-Central-Florida.h91093651.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/122000000/121860000/121857300/121857215/626ae4d3.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)

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

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

Fairview Shores

$239 nightly

$266 total

Mar 29 - Mar 30

Total with taxes and fees

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

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/18df6c8b.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)

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

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

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

Fairview Shores

$184 nightly

$204 total

Mar 29 - Mar 30

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/c1954c59.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.com/Orlando-Hotels-Money-Saving-Clean-Small-11-Private-Apartment-On-The-Orlando-Border.h121551588.Hotel-Information)

Fairview Shores

$99 nightly

$109 total

Mar 26 - Mar 27

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/a9cacec8.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.com/Orlando-Hotels-Serene-Mid-Century-32-WBonus-Room-And-Huge-Shaded-Yard-WFence.h91693626.Hotel-Information)

Goldenrod

10/10

Exceptional

(1 review)

"We thoroughly enjoyed our stay! Everything was clean, comfortable, and quiet. Very easy access to local restaurants and shopping, and a short drive to theme parks. We would definitely stay here again! Thank you! "

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

Megan J.

$360 nightly

$401 total

Apr 1 - Apr 2

Total with taxes and fees

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

![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)

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

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

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

Fairview Shores

7.0/10

Good

(2 reviews)

"Very clean and location was great"

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

Vicki V.

$216 nightly

$241 total

Mar 29 - Mar 30

Total with taxes and fees

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

![Private kitchen](https://images.trvl-media.com/lodging/128000000/127430000/127424700/127424651/5cf5ea37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/128000000/127430000/127424700/127424651/9fe1a268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/128000000/127430000/127424700/127424651/b90bbc87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/128000000/127430000/127424700/127424651/50674d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cute 5-bedroom house in peaceful Winter Park

[](https://www.expedia.com/Orlando-Hotels-Cute-5-Bedroom-House-In-Peaceful-Winter-Park.h127424651.Hotel-Information)

Winter Park

$358 nightly

$396 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Cute-5-Bedroom-House-In-Peaceful-Winter-Park.h127424651.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/c29ed280.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)

### Funky Remodeled Otown Bungalow Sleeps 8

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

Fairview Shores

$246 nightly

$274 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/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)

![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.com/Orlando-Hotels-Mills-House-WP-Sleeps-11-Renovated-Queen-Beds.h119712429.Hotel-Information)

Fairview Shores

8.0/10

Very Good

(2 reviews)

"Comfortable beds and plentiful TV screens. Nice central location to shopping and dining. Lights are bright without dimming options, and some fixtures not working. "

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

Larry S.

$293 nightly

$326 total

Apr 12 - Apr 13

Total with taxes and fees

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

![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)

![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)

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

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

Winter Park

10/10

Exceptional

(1 review)

"The house was clean, in a quiet neighborhood. Everything you could need was close and traffic was not bad at all. The host answers any and all questions quick and made the experience hassle free."

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

Stephanie S.

$316 nightly

$351 total

Apr 13 - Apr 14

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/119000000/118790000/118783100/118783079/18dcac50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118790000/118783100/118783079/7ad5d1d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118790000/118783100/118783079/e293f7a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118790000/118783100/118783079/2813a8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious Modern Japandi Retreat - Winter Park

[](https://www.expedia.com/Orlando-Hotels-Spacious-Modern-Japandi-Retreat-Winter-Park.h118783079.Hotel-Information)

Winter Park

10/10

Exceptional

(6 reviews)

"Clean house, good location to where we wanted to be!"

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

Jennifer M.

$459 nightly

$508 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Spacious-Modern-Japandi-Retreat-Winter-Park.h118783079.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)

![Living area](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/0312eb1a.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)

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

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

[](https://www.expedia.com/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.

$499 nightly

$553 total

Apr 20 - Apr 21

Total with taxes and fees

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

![Restaurant](https://images.trvl-media.com/lodging/1000000/790000/787900/787845/17d9fa97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/790000/787900/787845/d1af3e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/790000/787900/787845/193d8a8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/787900/787845/d663425f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites Orlando Int'l Drive/Convention Center

[](https://www.expedia.com/Orlando-Hotels-Fairfield-Inn-Suites-Orlando-Intl-DriveConvention-Center.h787845.Hotel-Information)

International Drive District

8.6/10

Excellent

(1,004 reviews)

"Great staff clean great breakfast and convenient location. "

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

Jessica

$99 nightly

$111 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Fairfield-Inn-Suites-Orlando-Intl-DriveConvention-Center.h787845.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)

![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)

![Apartment | 2 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/99000000/98470000/98469800/98469736/1d758b0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/99000000/98470000/98469800/98469736/40f281d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Front Porch

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

Sanford

9.0/10

Wonderful

(4 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

$205 nightly

$230 total

Mar 31 - Apr 1

Total with taxes and fees

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

![Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services](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 | 50-inch LED TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/100000000/99360000/99353800/99353747/w4032h3012x0y7-d90d4baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | Private kitchen | Mini-fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99360000/99353800/99353747/590198f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | 1 bedroom, desk, free WiFi](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.com/Sanford-Hotels-Boho-Nights.h99353747.Hotel-Information)

Sanford

9.4/10

Exceptional

(12 reviews)

"Wonderful spot, and excellent hosts!"

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

Thomas

$140 nightly

$157 total

Mar 30 - Mar 31

Total with taxes and fees

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

![Beach](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/0ba4a661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/3011289f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/bbd3365c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/95ab5ded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tiny Hidden Cottage 

[](https://www.expedia.com/Orlando-Hotels-Tiny-Cottage.h88627180.Hotel-Information)

Longwood

9.4/10

Exceptional

(63 reviews)

"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."

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

Anna M.

$131 nightly

$144 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Tiny-Cottage.h88627180.Hotel-Information)

![Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services](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 | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/e1a32506.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 | Private kitchen | Mini-fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/6e8626f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Blue Aztec

[](https://www.expedia.com/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

$218 nightly

$235 total

Mar 29 - Mar 30

Total with taxes and fees

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

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109750000/109748100/109748076/44ea1667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109750000/109748100/109748076/ab0c5991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/110000000/109750000/109748100/109748076/64dcb1df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109750000/109748100/109748076/w1284h1701x0y0-a0042edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

[](https://www.expedia.com/Orlando-Hotels-Charming-2-Bedroom-Apartment-With-WiFi.h109748076.Hotel-Information)

Orlando

9.8/10

Exceptional

(11 reviews)

"Great host, and stayed connected with us."

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

Christopher

$225 nightly

$251 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Charming-2-Bedroom-Apartment-With-WiFi.h109748076.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.com/Hotel-Search?startDate=2026-04-08&endDate=2026-04-09&regionId=7902&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CONDO)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VACATION_HOME)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=COTTAGE)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CABIN)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CHALET)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=HOUSE_BOAT)

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## Top Winter Park Hotel Reviews

![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/91c45539_y.jpg)

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

6/10 Okay

"Service was disappointing and did not match the price. For what we paid, we expected much better overall quality and attention."

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

![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg)

### Westgate Lakes Resort & Spa Universal Studios Area

6/10 Okay

"It’s very hard to find a parking spot near your room, the "

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

![Coco Key Hotel & Water Park Resort](https://images.trvl-media.com/lodging/1000000/10000/300/228/84c2249c_y.jpg)

### Coco Key Hotel & Water Park Resort

10/10 Excellent

"Loved "

[](https://expedia.com/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information)

![Sonesta Essential Orlando Airport](https://images.trvl-media.com/lodging/1000000/460000/455400/455359/13049557_y.jpg)

### Sonesta Essential Orlando Airport

2/10 Terrible

"Lobby not clean Rooms clean at the third day stayed. 😳😕"

[](https://expedia.com/Orlando-Hotels-Sonesta-Essential-Orlando.h455359.Hotel-Information)

![Marriott's Grande Vista](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/w4000h2662x0y0-7b7256af_y.jpg)

### Marriott's Grande Vista

10/10 Excellent

"My room was nice and clean and the kids loved watching March Madness on the large screen in the pool area "

[](https://expedia.com/Orlando-Hotels-Marriotts-Grande-Vista.h853519.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

8/10 Good

"Seems to be an older property but was clean and in good repair. Staff was friendly and competent. Good value for the money. Being close to Universal Orlando was a plus. Would recommend to my friends…"

[](https://expedia.com/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.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

"."

[](https://expedia.com/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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

8/10 Good

"Very nice resort, great amenities. Shuttle to parks, Starbucks in the hotel Enjoyed it until the last night when a tidal wave of teens came in and you know the rest. Non-stop ruckus. Overall, very satisfied with my stay!"

[](https://expedia.com/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.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

6/10 Okay

"Laundry facility not working properly hot tub cold "

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

## Find out more about Winter Park

**Everything you need to know about Winter Park vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winter Park vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winter Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $96 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Winter Park rentals**

At Expedia, we put the best Winter Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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- [Vacation Homes in Winter Park ](https://expedia.com/Winter-Park-Private-Vacation-Homes.d7902-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Winter Park ](https://expedia.com/Winter-Park-Condos.d7902-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Winter Park ](https://expedia.com/Winter-Park-Apartments.d7902-aaApartments.Travel-Guide-Accommodation)
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- [Cabin Rentals in Winter Park ](https://expedia.com/Winter-Park-Cabins.d7902-aaCabins.Travel-Guide-Accommodation)
- [Residences in Winter Park ](https://expedia.com/Winter-Park-Residences.d7902-aaResidences.Travel-Guide-Accommodation)
- [Hostels in Winter Park ](https://expedia.com/Winter-Park-Hostels.d7902-aaHostels.Travel-Guide-Accommodation)
- [RV Parks in Winter Park ](https://expedia.com/Winter-Park-RV-Parks.d7902-aaRVParks.Travel-Guide-Accommodation)
- [Riads in Winter Park ](https://expedia.com/Winter-Park-Riads.d7902-aaRiads.Travel-Guide-Accommodation)
- [Castles in Winter Park ](https://expedia.com/Winter-Park-Castles.d7902-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Winter Park?

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

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

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

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

### Expedia's Latest Trends

Hotels

- [Best Hotels in Altamonte Springs](https://expedia.com/Altamonte-Springs-Hotels.d5965.Travel-Guide-Hotels)
- [Extended Stay Hotels in Kissimmee](https://expedia.com/Kissimmee-Hotels-Extended-Stay-Hotels.0-0-d7927-tExtendedStayHotels.Travel-Guide-Filter-Hotels)
- [Best Hotels in Celebration](https://expedia.com/Celebration-Hotels.d602896.Travel-Guide-Hotels)
- [Lake Buena Vista Cheap Hotels](https://expedia.com/Lake-Buena-Vista-Hotels-Cheap-Hotels.0-0-d10870-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Kissimmee Pet-friendly Hotels](https://expedia.com/Kissimmee-Hotels-Pet-Friendly-Hotel.0-0-d7927-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Best Hotels in Maitland](https://expedia.com/Maitland-Hotels.d8442.Travel-Guide-Hotels)
- [Best Hotels in Kissimmee](https://expedia.com/Kissimmee-Hotels.d7927.Travel-Guide-Hotels)
- [Best Hotels in Windermere](https://expedia.com/Windermere-Hotels.d6085091.Travel-Guide-Hotels)
- [Kissimmee Hotels with a Lazy River](https://expedia.com/Kissimmee-Hotels-Hotels-With-A-Lazy-River.0-0-d7927-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels)
- [Kissimmee Casinos](https://expedia.com/Kissimmee-Hotels-Casino-Hotel.0-0-d7927-tCasinoHotel.Travel-Guide-Filter-Hotels)
- [Lake Buena Vista Hotels with Free Breakfast](https://expedia.com/Lake-Buena-Vista-Hotels-Hotels-With-Complimentary-Breakfast.0-0-d10870-tHotelswithComplimentaryBreakfast.Travel-Guide-Filter-Hotels)
- [Best Hotels in Lake Buena Vista](https://expedia.com/Lake-Buena-Vista-Hotels.d10870.Travel-Guide-Hotels)
- [Kissimmee Waterpark Hotels](https://expedia.com/Kissimmee-Hotels-Waterpark-Hotels.0-0-d7927-tWaterparkHotels.Travel-Guide-Filter-Hotels)
- [Kissimmee Cheap Hotels](https://expedia.com/Kissimmee-Hotels-Cheap-Hotels.0-0-d7927-tCheapHotels.Travel-Guide-Filter-Hotels)

Flights

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

Cars

- [Car rentals in Lake Buena Vista](https://expedia.com/Car-Rentals-In-Lake-Buena-Vista.d10870.Car-Rental-Guide)
- [Car rentals in Kissimmee](https://expedia.com/Car-Rentals-In-Kissimmee.d7927.Car-Rental-Guide)
- [Enterprise Car Rentals In Kissimmee](https://expedia.com/Enterprise-Car-Rentals-In-Kissimmee.d7927-c15.Car-Rental-Guide-Suppliers)
- [Car rentals in Altamonte Springs](https://expedia.com/Car-Rentals-In-Altamonte-Springs.d5965.Car-Rental-Guide)
- [Car rentals in Celebration](https://expedia.com/Car-Rentals-In-Celebration.d602896.Car-Rental-Guide)

Activities

- [Things to do in Lake Buena Vista](https://expedia.com/Things-To-Do-In-Lake-Buena-Vista.d10870.Travel-Guide-Activities)
- [Things to do in Kissimmee](https://expedia.com/Things-To-Do-In-Kissimmee.d7927.Travel-Guide-Activities)
- [Things to do in Altamonte Springs](https://expedia.com/Things-To-Do-In-Altamonte-Springs.d5965.Travel-Guide-Activities)
- [Things to do in Celebration](https://expedia.com/Things-To-Do-In-Celebration.d602896.Travel-Guide-Activities)

Packages

- [Kissimmee Packages](https://expedia.com/Kissimmee.d7927.Destination-Travel-Guides)
- [Celebration Packages](https://expedia.com/Celebration.d602896.Destination-Travel-Guides)

Vacation Rentals

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

General

- [Visit Kissimmee](https://expedia.com/Kissimmee.dx7927)
- [Visit Celebration](https://expedia.com/Celebration.dx602896)