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)

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## Check prices for these dates

In two weeks

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

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

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-07-10&endDate=2026-07-12&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)

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

![Smart TV](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/b4b96d1f.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.

$262 nightly

$291 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)

![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)

![Interior](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/ad8a3de4.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)

### 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 23 - Mar 24

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)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/a4a236a2.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)

![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.

$166 nightly

$184 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)

![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)

![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)

![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)

### Vacation Home in Fairview Shores

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

$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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/9bd56f27.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)

$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)

![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 23 - Mar 24

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)

### Vacation Home in Goldenrod

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

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.

$371 nightly

$413 total

Mar 23 - Mar 24

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)

![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)

![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)

### Vacation Home in Fairview Shores

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

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.

$213 nightly

$237 total

Mar 23 - Mar 24

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)

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

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

### Vacation Home in Winter Park

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

$365 nightly

$403 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/a352947e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Vacation Home in Fairview Shores

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

$246 nightly

$274 total

Mar 29 - Mar 30

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)

![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)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/b29eebc8.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)

### 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)

"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.

$289 nightly

$322 total

Mar 25 - Mar 26

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)

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

### Vacation Home in Winter Park

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

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.

$349 nightly

$387 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)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118790000/118783100/118783079/94559350.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)

### Vacation Home in Winter Park

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

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.

$491 nightly

$543 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)

![Exterior](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/3aa946ab.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)

### 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.

$531 nightly

$589 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)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/790000/787900/787845/c5edae4a.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)

### Hotel in International Drive District

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

8.6/10

Excellent

(1,001 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)

![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)

![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)

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

### Apartment in Sanford

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

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 23 - Mar 24

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)

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

![Standard Apartment | 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)

### Apartment in Sanford

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

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

Apr 2 - Apr 3

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)

![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/89000000/88630000/88627200/88627180/27963cae.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)

### Cottage in Longwood

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

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

Mar 23 - Mar 24

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)

![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 24 - Mar 25

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)

![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)

![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)

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 23 - Mar 24

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=2026-04-05&endDate=2026-04-06&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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&lodging=VACATION_HOME)

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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&lodging=APARTMENT)

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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&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=2026-06-19&d1=2026-06-19&endDate=2026-06-22&d2=2026-06-22&lodging=HOUSE_BOAT)

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## Top Winter Park Hotel Reviews

![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

6/10 Okay

"Noce renovat"

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

"Very clean , pretty , near everything "

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

"Great value for an onsite resort"

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

6/10 Okay

"I’m honestly not sure if this was due to spring break crowds, but this was not one of the best experiences I’ve had at this hotel. I stayed here years ago and it was a completely different experience—in a good way. Unfortunately, the property has gone downhill significantly. There was no mention on the website about renovations, and the water park was very limited during our stay. None of the slides were available, which was a huge disappointment. Check-in lines were extremely long, and several elevators were out of service, making it even more frustrating getting around. The room itself was not up to par—the bathrooms especially needed attention. Housekeeping was also an issue. We had four people in our room and were only given two towels, and it took multiple requests to get anything additional. Even when the hotel reached out via text to ask about our stay, there was little to no follow-up when concerns were raised, which made the service feel very surface-level. Another concern was the environment—there was a noticeable smell of marijuana throughout different areas of the resort, which made the overall atmosphere less family-friendly than expected. Overall, I’m very disappointed with this stay. The only positive experience was the woman who checked us in—she was incredibly kind and welcoming, and truly the highlight of our visit."

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

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

### Lake Buena Vista Resort Village & Spa

10/10 Excellent

"I stay at this place every times when I am in Orlando. Wonderful place and excellent staff"

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

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

### Sonesta Essential Orlando Airport

4/10 Poor

"Disclaimer: I did not call the front desk, we were there one night to be closer to the airport. I basically didn’t want to deal with it. No hot water, seemed as though mixer in shower was broken. Large gap under the door. One of the safety mechanisms on the door was broken. I went to plug in a charger next to bed outlet did not work at all. Plugged in across room, when I attempted to first plug it in a spark shot out. I used my own battery pack. Dirty cleaning rag left in bathroom. Two random light switches that didn’t seem to control anything in the room. I wouldn’t stay here again. I will say the lobby staff was okay and the entire place did smell clean. "

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

10/10 Excellent

"clean room. in and out very easy"

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

![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/075cd42b_y.jpg)

### Caribe Royale Orlando

10/10 Excellent

"The Caribe Royale has professional staff who work hard, have great customer service skills and do what they can to show you that they want you to enjoy your stay. The property is absolutely beautiful and well maintained both inside and out. The rooms we stayed in were very beautiful and comfortable. There are also beautiful birds that can be sighted on the grounds which is also nice. There is a large pool with a slide, plenty of seating around the pool, a poolside restaurant, a basketball court, and various other amenities that guests can enjoy."

[](https://expedia.com/Orlando-Hotels-Caribe-Royale-Orlando.h40865.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

10/10 Excellent

"Did not use"

[](https://expedia.com/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.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)
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- [Guest Houses in Winter Park ](https://expedia.com/Winter-Park-Guest-Houses.d7902-aaGuestHouses.Travel-Guide-Accommodation)
- [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 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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