Title: Winter Park Vacation Rentals from $102: 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)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three 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 four 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)

## Our top choices for Winter Park vacation rentals

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

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

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

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/9dff99a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in College Park

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

8.0/10

Very Good

(2 reviews)

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

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

Danielle H.

$238 nightly

$265 total

Mar 16 - Mar 17

Total with taxes and fees

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

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

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

![Smart TV, books, computer monitors](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/626ae4d3.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)

### Vacation Home in Fairview Shores

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

$227 nightly

$253 total

Mar 9 - Mar 10

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/f1476d84.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)

### Mobile Home in Fairview Shores

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

$172 nightly

$191 total

Mar 9 - Mar 10

Total with taxes and fees

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

![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, 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)

### Apartment in Orlando

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

9.4/10

Exceptional

(3 reviews)

"Fantastic Host"

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

Marek K.

$170 nightly

$188 total

Apr 1 - Apr 2

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)

![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)

![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/57a8906a.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)

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

### Apartment in Orlando

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

10/10

Exceptional

(2 reviews)

"Pool is very inviting"

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

Geri Lamborn M.

$265 nightly

$296 total

Apr 1 - Apr 2

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)

![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)

### Vacation Home in Fairview Shores

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

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 9 - Mar 10

Total with taxes and fees

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

![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)

### Apartment in Fairview Shores

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

$99 nightly

$109 total

Mar 9 - Mar 10

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)

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/fc26e60e.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)

### Vacation Home in Fairview Shores

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

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.

$217 nightly

$242 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)

![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)

![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)

![Interior](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/a9cacec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Goldenrod

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

$345 nightly

$384 total

Mar 10 - Mar 11

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)

![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/c29ed280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Home in Fairview Shores

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

$227 nightly

$253 total

Mar 9 - Mar 10

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/b29eebc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Home in Fairview Shores

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

8.0/10

Very Good

(2 reviews)

"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.

$286 nightly

$319 total

Mar 17 - Mar 18

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)

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

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/18ad5479.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)

### Vacation Home in Winter Park

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

$302 nightly

$336 total

Mar 30 - Mar 31

Total with taxes and fees

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

### Vacation Home in Winter Park

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

4.0/10

(1 review)

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

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

Nyssa S.

$546 nightly

$605 total

Mar 31 - Apr 1

Total with taxes and fees

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

![Marina](https://images.trvl-media.com/lodging/84000000/83800000/83792800/83792752/cb35eef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83800000/83792800/83792752/e8eaf978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/84000000/83800000/83792800/83792752/80c8c211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books, offices](https://images.trvl-media.com/lodging/84000000/83800000/83792800/83792752/69a8c75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Orlando

[](https://www.expedia.com/Orlando-Hotels-NEW-Designed-Apt-2023-NrUCF-PETSOk-PrivateEntry.h83792752.Hotel-Information)

9.2/10

Wonderful

(13 reviews)

"I stayed at the property from Oct 31st to Nov 2nd for the weekend. This is a very cozy and clean studio apartment which was perfect fo myself and my 2 dogs. There is a fenced in yard at lights at night so my dogs really enjoyed it also. "

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

michael

$159 nightly

$168 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-NEW-Designed-Apt-2023-NrUCF-PETSOk-PrivateEntry.h83792752.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/34096aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sanford

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

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 9 - Mar 10

Total with taxes and fees

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

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100600000/100590500/100590461/ff8514dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100600000/100590500/100590461/07c4f574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/101000000/100600000/100590500/100590461/4a353a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100600000/100590500/100590461/5235ae01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Southchase

[](https://www.expedia.com/Orlando-Hotels-Cozy-Apartment-In-S-Orlando.h100590461.Hotel-Information)

9.8/10

Exceptional

(22 reviews)

"Everything was amazing described how it was owners were super sweet and loving we were happy to find this place to stay "

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

Pamela Y.

$117 nightly

$129 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Cozy-Apartment-In-S-Orlando.h100590461.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 | 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)

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

### Apartment in Sanford

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

9.4/10

Exceptional

(11 reviews)

"Wonderful spot, and excellent hosts!"

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

Thomas

$140 nightly

$157 total

Mar 9 - Mar 10

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88670000/88666400/88666325/5ebada83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/89000000/88670000/88666400/88666325/271a7b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88670000/88666400/88666325/3127e9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/89000000/88670000/88666400/88666325/9af3e32a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sanford

[](https://www.expedia.com/Sanford-Hotels-The-Blue-Aztec.h88666325.Hotel-Information)

10/10

Exceptional

(12 reviews)

"Perfect location within walking distance of all the fun yet nice and quiet. Place was squeaky clean. Will stay again"

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

Min O.

$163 nightly

$173 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Sanford-Hotels-The-Blue-Aztec.h88666325.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)

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

### Apartment in Orlando

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

10/10

Exceptional

(10 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 9 - Mar 10

Total with taxes and fees

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

![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)

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

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

### Vacation Home in Union Park

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

9.8/10

Exceptional

(22 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.

$240 nightly

$268 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-La-Casita-Pool-Oasis.h89401769.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=2026-03-22&endDate=2026-03-23&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.com/deals?rfrr=VR_SPRING_PROMO_7902)

## Find vacation rentals that suit your style

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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=CONDO)

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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=COTTAGE)

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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=APARTMENT)

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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&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=2026-06-06&d1=2026-06-06&endDate=2026-06-09&d2=2026-06-09&lodging=HOUSE_BOAT)

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## Top Winter Park Hotel Reviews

![Orlando International Drive North Hotel](https://images.trvl-media.com/lodging/1000000/50000/41500/41493/fcd15e0d_y.jpg)

### Orlando International Drive North Hotel

6/10 Okay

"Yes"

[](https://expedia.com/Orlando-Hotels-Orlando-International-Drive-North-Hotel.h41493.Hotel-Information)

![Hyatt Place Orlando/Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/30000/24000/23965/698d5998_y.jpg)

### Hyatt Place Orlando/Lake Buena Vista

10/10 Excellent

"Very clean, great staff !!"

[](https://expedia.com/Orlando-Hotels-Hyatt-Place-OrlandoLake-Buena-Vista.h23965.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

"The property was extremely clean and relaxing. Villa rooms were nice and spacious. Perfect for a family or a group of friends. I’d definitely travel here again."

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

![Four Points by Sheraton Orlando International Drive](https://images.trvl-media.com/lodging/1000000/10000/4300/4262/c6e39ea9_edited_40eb_y.jpg)

### Four Points by Sheraton Orlando International Drive

4/10 Poor

"First it started great pulled in early to grab the shuttle to Universal Studios my room was ready so awesome early check-in. Great start right.... well with a 7 year old he wants to swim, play in the arcade, run around on the splash pad, and at the end of the night eat some pizza. Mom and son trip here we go. Welp... arcade has a handful of games geared for big teens/adults, pool is okay alittle small with it being a family hotel splash pad never turned on so not sure if was broke or not. Well now its the end of the day moms tired boy is tired and what do i do but bribe my boy if we hurry we can swim and get pizza before the close it all down at 10PM crazy i know right family hotel catering to families in the park you think they would stay open till 11 or midnight (not like their paying lifeguards) but nope 10pm bit wait heres the kicker dont believe in the posted signs everywhere telling you can get food and drinks till 10... its a lie drinks yes so grab a shot before you head out again to go find food because kitchen closes at 930 but feel free to do some miniature golf in front of the hotel people were folfing till midnight!!!! Extremely unhappy momma there... and ti TOP IT OFF I WAS ASKED AT CHECK IN IF ID BE INSTRESTED IN LOOKING INTO A TIMESHARE WITH THEIR MORE UPSCALE HOTEL JUST DOWN THE ROAD!!!!"

[](https://expedia.com/Orlando-Hotels-Four-Points-By-Sheraton-Orlando-International-Drive.h4262.Hotel-Information)

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

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

10/10 Excellent

"The shuttle was so convenient. The rooms were spacious. The pool and fitness center were great. The staff were very helpful. I love that they gave us a number to text if we needed anything. I definite will stay there again. "

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

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

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

10/10 Excellent

"Yes. We enjoy the pool. "

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

10/10 Excellent

"A good night sleep"

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

![Holiday Inn Resort Orlando Suites - Waterpark by IHG](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/9a7827e4_y.jpg)

### Holiday Inn Resort Orlando Suites - Waterpark by IHG

8/10 Good

"Lawn care started at 6am. I understand that leaf blowers need to run. But 6am was a little ridiculous. "

[](https://expedia.com/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Suites-Waterpark.h281608.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

"I have stayed here several times, it is always clean and the breakfast is good. "

[](https://expedia.com/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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 $102 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)
- [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)
- [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)
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- [B&B in Winter Park ](https://expedia.com/Winter-Park-Bed-And-Breakfast.d7902-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Winter Park ](https://expedia.com/Winter-Park-Chalets.d7902-aaChalets.Travel-Guide-Accommodation)
- [Motels in Winter Park ](https://expedia.com/Winter-Park-Motels.d7902-aaMotels.Travel-Guide-Accommodation)
- [Condo Resorts in Winter Park ](https://expedia.com/Winter-Park-Condominium-Resort.d7902-aaCondominiumResort.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)
- [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

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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)
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Flights

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

Cars

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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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