Title: Winter Park Vacation Rentals from $100: 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)

![](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

[Apr 17 - Apr 19](https://www.expedia.com/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 two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-07-24&endDate=2026-07-26&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)

![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, 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)

![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 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.

$157 nightly

$174 total

Apr 27 - Apr 28

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)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/1a1d4665.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)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/c1954c59.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)

### 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

Apr 2 - Apr 3

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)

![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)

![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/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

Apr 2 - Apr 3

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/6f9b109b.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

Apr 2 - Apr 3

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/081e1921.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)

### 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.

$254 nightly

$283 total

Apr 13 - Apr 14

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/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)

![Exterior detail](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/64430b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Boutique Guest house in Winter Park 

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

Winter Park

10/10

Exceptional

(106 reviews)

"Excellent location, peaceful setting "

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

Christy M.

$301 nightly

$335 total

Apr 14 - Apr 15

Total with taxes and fees

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

![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)

![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)

### 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

$240 nightly

$267 total

Apr 22 - Apr 23

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/128000000/127430000/127424700/127424651/d34e4e4e.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

$357 nightly

$395 total

Apr 2 - Apr 3

Total with taxes and fees

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

![Smart TV](https://images.trvl-media.com/lodging/101000000/100690000/100688000/100687935/08c17f0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100690000/100688000/100687935/f1746a8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100690000/100688000/100687935/53c487b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/101000000/100690000/100688000/100687935/bf9b8236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winter Park Charmer - Heated Pool Home - Close to everything

[](https://www.expedia.com/Winter-Park-Hotels-Winter-Park-Charmer-Heated-Pool-Home-Close-To-Everything.h100687935.Hotel-Information)

Winter Park

8.0/10

Very Good

(14 reviews)

"Not as advertised, very disappointed. Got in from a red eye flight and thought we could relax around the pool. But it was unkept and full of algae. Stained black mold all around the pool. And mold on the furniture and pool floats. Not a pleasant start to our family vacation."

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

Jon F.

$379 nightly

$420 total

Apr 3 - Apr 4

Total with taxes and fees

[](https://www.expedia.com/Winter-Park-Hotels-Winter-Park-Charmer-Heated-Pool-Home-Close-To-Everything.h100687935.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)

![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)

![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/121000000/120190000/120187300/120187220/7253cdd8.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.

$201 nightly

$224 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Charming-Home-Wp-Patio-Gazebo-Close-To-Highwys.h120187220.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/a9cacec8.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.com/Orlando-Hotels-Serene-Mid-Century-32-WBonus-Room-And-Huge-Shaded-Yard-WFence.h91693626.Hotel-Information)

Goldenrod

10/10

Exceptional

(3 reviews)

"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.

$364 nightly

$405 total

Apr 6 - Apr 7

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)

![Interior](https://images.trvl-media.com/lodging/119000000/118790000/118783100/118783079/18dcac50.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)

![Dining](https://images.trvl-media.com/lodging/119000000/118790000/118783100/118783079/7ad5d1d9.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.

$421 nightly

$467 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)

![Living area](https://images.trvl-media.com/lodging/84000000/83190000/83185200/83185152/72e0c58f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/84000000/83190000/83185200/83185152/c43516fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/84000000/83190000/83185200/83185152/01c88c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/84000000/83190000/83185200/83185152/9fc3078d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### WINTER PARK TOWNHOUSE - NEAR DOWNNTOWN & PARKS 

[](https://www.expedia.com/Orlando-Hotels-WINTER-PARK-TOWNHOUSE-NEAR-DOWNNTOWN-PARKS.h83185152.Hotel-Information)

College Park

9.0/10

Wonderful

(2 reviews)

"We had a great time! Home was clean, roomy and all we had hoped for. The hosts were very communicative and quick to answer all our questions prior to our stay! Would definitely recommend!"

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

Rita C.

$565 nightly

$628 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-WINTER-PARK-TOWNHOUSE-NEAR-DOWNNTOWN-PARKS.h83185152.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.com/Orlando-Hotels-Funky-Remodeled-Otown-Bungalow-Sleeps-8.h123147976.Hotel-Information)

Fairview Shores

$253 nightly

$282 total

Apr 19 - Apr 20

Total with taxes and fees

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

![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/122000000/121020000/121017300/121017283/9e87b9ef.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)

### 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.

$313 nightly

$347 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)

![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)

![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.

$283 nightly

$315 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/121000000/120490000/120489000/120488903/437efd0b.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)

![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)

### 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.

$479 nightly

$531 total

Apr 27 - Apr 28

Total with taxes and fees

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

(64 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 | 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)

![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)

### 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

Apr 6 - Apr 7

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/w1284h1701x0y0-a0042edf.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)

![Interior](https://images.trvl-media.com/lodging/110000000/109750000/109748100/109748076/ca507c3a.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

(12 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

Apr 4 - Apr 5

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=2026-04-15&endDate=2026-04-16&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.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APART_HOTEL)

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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=VACATION_HOME)

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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CONDO)

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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=VILLA)

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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APARTMENT)

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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CABIN)

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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=HOUSE_BOAT)

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=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CHALET)

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## Top Winter Park Hotel Reviews

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

### Rosen Inn Lake Buena Vista

8/10 Good

"For a one night stay it was good. We didn’t use the pool , but it looked very nice. "

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

![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/4c48bd3d_y.jpg)

### Universal's Cabana Bay Beach Resort

10/10 Excellent

"I would definitely stay here again! Next time longer! "

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

![Hyatt Regency Orlando International Airport](https://images.trvl-media.com/lodging/1000000/10000/2800/2754/928976cc_y.jpg)

### Hyatt Regency Orlando International Airport

8/10 Good

"Very clean & nice. "

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

![Drury Plaza Hotel Orlando - Disney Springs Area](https://images.trvl-media.com/lodging/1000000/30000/24200/24103/6af5b762_y.jpg)

### Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"Clean room , friendly staff "

[](https://expedia.com/Orlando-Hotels-Drury-Plaza-Hotel-Orlando-Lake-Buena-Vista.h24103.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

"Beautiful room, except my socks and feet were filthy from the floor. Had trouble twice with my room key and had to wait outside. I was there 2 1/2 days to join my son. He went on the 90 minute tour and they wouldn't stop pressuring him to buy. He was gone 5 hours! As I sat waiting for him alone. The pool chairs fill up fast because people get down there early and save many chaises along with a table. Then no one shows up.to sit in them for a couple hours. A lot of walking especially to the adult pool. No body lotion in rooms.Everything is overpriced."

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

![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/cae40483_y.jpg)

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

8/10 Good

"All good."

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

![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/4ca8f177_y.jpg)

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

10/10 Excellent

"Pool was great "

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

![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

8/10 Good

"Very long wait to get into our room when registering. Had to request toilet paper, no extras in room. Still love this resort and location"

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

"Visited CoCo Key in late March with my 6 and 9 year old daughters. We loved the hotel- were some things run down sure but for the price the place was great. The food was about 6/7 out of 10 (would suggest grabbing snacks before arriving), drinks were expensive but good, staff was excellent and most importantly- we felt safe while staying there. My girls were able to roam back and forth from pools and I was never worried on safety. We would 100% book this place again."

[](https://expedia.com/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.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 $100 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.

## Explore a world of travel with Expedia

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- [Vacation Homes in Winter Park ](https://expedia.com/Winter-Park-Private-Vacation-Homes.d7902-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Winter Park ](https://expedia.com/Winter-Park-Apartments.d7902-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Winter Park ](https://expedia.com/Winter-Park-Condos.d7902-aaCondos.Travel-Guide-Accommodation)
- [Villas in Winter Park ](https://expedia.com/Winter-Park-Villas.d7902-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Winter Park ](https://expedia.com/Winter-Park-Resorts.d7902-aaResorts.Travel-Guide-Accommodation)
- [Cottages in Winter Park ](https://expedia.com/Winter-Park-Cottages.d7902-aaCottages.Travel-Guide-Accommodation)
- [Aparthotels in Winter Park ](https://expedia.com/Winter-Park-Apart-Hotels.d7902-aaApartHotels.Travel-Guide-Accommodation)
- [Town Houses in Winter Park ](https://expedia.com/Winter-Park-Town-Houses.d7902-aaTownHouses.Travel-Guide-Accommodation)
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- [B&B in Winter Park ](https://expedia.com/Winter-Park-Bed-And-Breakfast.d7902-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Motels in Winter Park ](https://expedia.com/Winter-Park-Motels.d7902-aaMotels.Travel-Guide-Accommodation)
- [Chalets in Winter Park ](https://expedia.com/Winter-Park-Chalets.d7902-aaChalets.Travel-Guide-Accommodation)
- [Houseboats in Winter Park ](https://expedia.com/Winter-Park-Houseboats.d7902-aaHouseboats.Travel-Guide-Accommodation)
- [Farmstay in Winter Park ](https://expedia.com/Winter-Park-Agritourism.d7902-aaAgritourism.Travel-Guide-Accommodation)
- [Lodges in Winter Park ](https://expedia.com/Winter-Park-Lodges.d7902-aaLodges.Travel-Guide-Accommodation)
- [RV Parks in Winter Park ](https://expedia.com/Winter-Park-RV-Parks.d7902-aaRVParks.Travel-Guide-Accommodation)
- [Residences in Winter Park ](https://expedia.com/Winter-Park-Residences.d7902-aaResidences.Travel-Guide-Accommodation)
- [Cabin Rentals in Winter Park ](https://expedia.com/Winter-Park-Cabins.d7902-aaCabins.Travel-Guide-Accommodation)
- [Hostels in Winter Park ](https://expedia.com/Winter-Park-Hostels.d7902-aaHostels.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

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- [Lake Buena Vista Cheap Hotels](https://expedia.com/Lake-Buena-Vista-Hotels-Cheap-Hotels.0-0-d10870-tCheapHotels.Travel-Guide-Filter-Hotels)
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- [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)
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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)
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- [Enterprise Car Rentals In Kissimmee](https://expedia.com/Enterprise-Car-Rentals-In-Kissimmee.d7927-c15.Car-Rental-Guide-Suppliers)
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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

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Vacation Rentals

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General

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

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