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

[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

![Studio | Private kitchen](https://images.trvl-media.com/lodging/125000000/124510000/124504400/124504382/ef9c185f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124510000/124504400/124504382/33780020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Free WiFi](https://images.trvl-media.com/lodging/125000000/124510000/124504400/124504382/612d5b4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124510000/124504400/124504382/7d8f8b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Casselberry

[](https://www.expedia.com/Casselberry-Hotels-Cozy-Modern-Studio.h124504382.Hotel-Information)

$150 nightly

$168 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Casselberry-Hotels-Cozy-Modern-Studio.h124504382.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99360000/99354400/99354343/a16fe447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99354400/99354343/1d542eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | 2 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/100000000/99360000/99354400/99354343/e115b0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/100000000/99360000/99354400/99354343/76809168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sanford

[](https://www.expedia.com/Sanford-Hotels-The-Contemporary.h99354343.Hotel-Information)

$265 nightly

$288 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Sanford-Hotels-The-Contemporary.h99354343.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/102000000/101420000/101419400/101419314/cba64ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101420000/101419400/101419314/f395a853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Suite | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101420000/101419400/101419314/72416e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101420000/101419400/101419314/91d4aa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Orlando

[](https://www.expedia.com/Orlando-Hotels-The-View-Studio-Suites-And-Event-Venue.h101419314.Hotel-Information)

8.4/10

Very Good

(1,771 reviews)

"Great place and good breakfast "

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

Suleidy

$95 nightly

$107 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-The-View-Studio-Suites-And-Event-Venue.h101419314.Hotel-Information)

![Apartment (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/120000000/119200000/119199600/119199504/79276ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119200000/119199600/119199504/8aa7203d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119200000/119199600/119199504/d44c74b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119200000/119199600/119199504/ef7280ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in International Drive District

[](https://www.expedia.com/Orlando-Hotels-Poolside-Bliss-Theme-Park-Thrills-Orlando-Oasis.h119199504.Hotel-Information)

$352 nightly

$393 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Poolside-Bliss-Theme-Park-Thrills-Orlando-Oasis.h119199504.Hotel-Information)

![House | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/114000000/113160000/113158900/113158893/9e832f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/114000000/113160000/113158900/113158893/0288f764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/114000000/113160000/113158900/113158893/3937d775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | 4 bedrooms, Internet](https://images.trvl-media.com/lodging/114000000/113160000/113158900/113158893/9543cf08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Kissimmee

[](https://www.expedia.com/Orlando-Hotels-Private-Disney-Oasis-With-Pool-Hot-Tub-Ps5-And-Modern-Amenities.h113158893.Hotel-Information)

[](https://www.expedia.com/Orlando-Hotels-Private-Disney-Oasis-With-Pool-Hot-Tub-Ps5-And-Modern-Amenities.h113158893.Hotel-Information)

![Bathroom](https://images.trvl-media.com/lodging/119000000/118940000/118938800/118938718/6ba821d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118940000/118938800/118938718/81927513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118940000/118938800/118938718/bf8bc9dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118940000/118938800/118938718/7a0d34fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Ventura

[](https://www.expedia.com/Orlando-Hotels-Vacational-Apartment-At-Orlando-3608.h118938718.Hotel-Information)

$173 nightly

$195 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Vacational-Apartment-At-Orlando-3608.h118938718.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99360000/99354200/99354105/f7360ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | Interior](https://images.trvl-media.com/lodging/100000000/99360000/99354200/99354105/2ce4f5fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | 1 bedroom, desk, free WiFi](https://images.trvl-media.com/lodging/100000000/99360000/99354200/99354105/23ef6654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | Interior](https://images.trvl-media.com/lodging/100000000/99360000/99354200/99354105/6347396c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sanford

[](https://www.expedia.com/Sanford-Hotels-The-Jazz-Loft.h99354105.Hotel-Information)

8.4/10

Very Good

(7 reviews)

"Location, location, location!!! What a cute and fun space. I thoroughly enjoyed my entire Jazz Loft experience. Look fwd to next trip! "

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

Deborah

$140 nightly

$157 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Sanford-Hotels-The-Jazz-Loft.h99354105.Hotel-Information)

![Hallway](https://images.trvl-media.com/lodging/120000000/119160000/119157700/119157665/f18d1fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119160000/119157700/119157665/9b4b4592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/120000000/119160000/119157700/119157665/5c3e1c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119160000/119157700/119157665/7eb7106d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Kissimmee

[](https://www.expedia.com/Orlando-Hotels-Enchanted-Fantasy.h119157665.Hotel-Information)

7.4/10

Good

(3 reviews)

"That’s very good"

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

Shamsuddin

$115 nightly

$131 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Enchanted-Fantasy.h119157665.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/7f8848b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/c6a2da7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/82a6ad82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mini-fridge, microwave, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/9d43162b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sanford

[](https://www.expedia.com/Sanford-Hotels-Bella-Breeze.h99355180.Hotel-Information)

9.6/10

Exceptional

(9 reviews)

"The place was very clean, the bed was comfortable, the communication with owners was excellent. It was a nice place to stay while we were in town. "

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

Michael

$140 nightly

$157 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Sanford-Hotels-Bella-Breeze.h99355180.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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/99000000/98470000/98469800/98469736/40f281d3.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)

### Apartment in Sanford

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

9.4/10

Exceptional

(3 reviews)

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

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

Johnny

$205 nightly

$230 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/125000000/124370000/124365700/124365680/c45524b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Condo, 1 Bedroom, Hot Tub | In-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/125000000/124370000/124365700/124365680/w2500h1665x0y1-290a7dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124370000/124365700/124365680/w2499h1406x1y1-6acb17ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Condo, 1 Bedroom, Hot Tub | Children's area](https://images.trvl-media.com/lodging/125000000/124370000/124365700/124365680/w2500h1667x0y1-77125562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Orlando

[](https://www.expedia.com/Orlando-Hotels-8303-Palm-Disney.h124365680.Hotel-Information)

$293 nightly

$332 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-8303-Palm-Disney.h124365680.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)

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

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

![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)

![Interior](https://images.trvl-media.com/lodging/124000000/123110000/123108700/123108673/616a6a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Private kitchen | Microwave, oven, highchair, blender](https://images.trvl-media.com/lodging/124000000/123110000/123108700/123108673/f1d5a4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/124000000/123110000/123108700/123108673/16c2105c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | 1 bedroom, blackout drapes, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/124000000/123110000/123108700/123108673/f7cb3f69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Orlando

[](https://www.expedia.com/Orlando-Hotels-Apartment-1-BR-Free-Shuttle-To-Disney-Parks.h123108673.Hotel-Information)

$241 nightly

$271 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Apartment-1-BR-Free-Shuttle-To-Disney-Parks.h123108673.Hotel-Information)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/e330205c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/03c563d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/96a79e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/0104505e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Deltona Lakes

[](https://www.expedia.com/Deltona-Hotels-Home-On-Lake.h93537181.Hotel-Information)

10/10

Exceptional

(3 reviews)

"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"

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

Anonymous traveler

$304 nightly

$339 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Deltona-Hotels-Home-On-Lake.h93537181.Hotel-Information)

![Apartment | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/122000000/121410000/121403600/121403556/w2998h1999x2y2-d150b5d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/122000000/121410000/121403600/121403556/w3000h1677x0y0-93e2d09b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/122000000/121410000/121403600/121403556/w2998h1999x2y2-acc69296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/122000000/121410000/121403600/121403556/b4ed61fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Ventura

[](https://www.expedia.com/Orlando-Hotels-Upstay-2BR-Golfer-S-Retreat-W-Patio-Ventura-Resort.h121403556.Hotel-Information)

$253 nightly

$284 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Upstay-2BR-Golfer-S-Retreat-W-Patio-Ventura-Resort.h121403556.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355400/99355379/c3eaf2ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment | Desk, free WiFi](https://images.trvl-media.com/lodging/100000000/99360000/99355400/99355379/00bcf942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355400/99355379/7fa08f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355400/99355379/263b4fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sanford

[](https://www.expedia.com/Sanford-Hotels-Totally-80s.h99355379.Hotel-Information)

7.4/10

Good

(6 reviews)

"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."

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

Serge

$132 nightly

$148 total

Mar 20 - Mar 21

Total with taxes and fees

[](https://www.expedia.com/Sanford-Hotels-Totally-80s.h99355379.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)

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

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

### 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

Mar 22 - Mar 23

Total with taxes and fees

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

![Deluxe Condo, 2 Bedrooms, Non Smoking | Balcony view](https://images.trvl-media.com/lodging/1000000/20000/13800/13780/90-7ff0a58f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Condo, 2 Bedrooms | Living area | 32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/20000/13800/13780/363da32d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/13800/13780/3f969b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/13800/13780/eeb74d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in International Drive District

[](https://www.expedia.com/Orlando-Hotels-Parc-Corniche-Condominium-Suite-Hotel.h13780.Hotel-Information)

8.0/10

Very Good

(2,232 reviews)

"Staff was very helpful. "

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

Ulrica

$127 nightly

$143 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Parc-Corniche-Condominium-Suite-Hotel.h13780.Hotel-Information)

![Condo, 2 Bedrooms | Exterior](https://images.trvl-media.com/lodging/91000000/90320000/90311900/90311840/5fc9ef8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/91000000/90320000/90311900/90311840/13f4cb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms | Interior](https://images.trvl-media.com/lodging/91000000/90320000/90311900/90311840/a1db3f1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/91000000/90320000/90311900/90311840/4b451942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Kissimmee

[](https://www.expedia.com/Orlando-Hotels-Serenity-Haven.h90311840.Hotel-Information)

[](https://www.expedia.com/Orlando-Hotels-Serenity-Haven.h90311840.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/17800/17739/3ccef447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17800/17739/d5ee5eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/1000000/20000/17800/17739/d6bf10f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/1000000/20000/17800/17739/c2ba60e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Orlando

[](https://www.expedia.com/Orlando-Hotels-Florida-Hotel-Conference-Center-In-The-Florida-Mall.h17739.Hotel-Information)

9.2/10

Wonderful

(2,535 reviews)

"The whole stay was fantastic!!"

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

Kristen

$233 nightly

$263 total

Apr 10 - Apr 11

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Florida-Hotel-Conference-Center-In-The-Florida-Mall.h17739.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=2026-04-02&endDate=2026-04-03&regionId=7902&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=HOUSE_BOAT)

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## Top Winter Park Hotel Reviews

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

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

8/10 Good

"The shuttles were amazing. Yhe airport shuttle as well as the shuttles to the park"

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

![B&B Hotel Orlando International Drive Near Universal - Newly Renovated!](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/ca31fce1_y.jpg)

### B&B Hotel Orlando International Drive Near Universal - Newly Renovated!

8/10 Good

"It will be better for customers who can take elevator for heavy luggage to the second floor."

[](https://expedia.com/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.Hotel-Information)

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

### Rosen Inn at Pointe Orlando

4/10 Poor

"I got there early and asked if I could check in and they said there would be a $30 early check in fee. The first room I had was facing the expressway and was extrememly loud and the room had a bad smell that I could no tolerate. The next room was in a much better location but it still had a funky smell. The rooms are just old and tired. The staff was great but the place needs an overhaul. Also.. the restaurant in the morning only offers the buffett at $18.30 with no menu option. I wasn't thrilled about my experience. One last thing, Expedia always says that this is the whole price you will pay, however there was a $10/night parking fee. I am okay with the $10, however, I am more dissapointed at Expedia for not letting me/us know that the price you see is NOT the price you get. "

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

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

### Caribe Royale Orlando

10/10 Excellent

"This property is really great! The lobby area, available restaurants and amenities are top notch. The room was spacious, the beds were comfortable and very clean. We will return to this property for sure! "

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

2/10 Terrible

"parking was a major issue had to pay an extra $33 per day for parking hotel was overbooked also parking spaces blocked by construction had to park very far from building even @5 pm had to back up multiple times bc gate wouldnt ipen to go through where thr old lobby was or back up bc of towel carts in the way where thr hotel does laundry or because of construction pool, slides flo rides and hot tub over crowded so hard to use amenities no lounge chairs reservations booked up for many hrs for flo rider took 40 mins to check into hotel management was horrible didnt care to provide top notch customer service towels and sheets had stains on them room had a bleach/ chlorine smell hotel was full so couldnt switch rooms they didnt take towels from bathroom floor on day of check out housekeeping came to our room and opened door 3 times and had do not disturb sign on door they didn't even knock when i called to make a complaint w a manager i was told no one was available and was told they would call me back to my room or cell never got a call the hotel went downhill majorly i stayed there 3 other times with in the last 12 years and id never stay there again the rooms need updating they are dingy and im honestly not the type to complain and write negative reviews but i was infuriated w our stay especially when it was almost 400 for two nights i couldve stayed somewhere else theres a hotel on every corner "

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

"Great stay, ask for deals to go to theme parks!"

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

"Cannot wait to go back!!!"

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

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

### Sonesta Essential Orlando Airport

8/10 Good

"Was ok for a one night stay. In the price point. Omly 2 complaints to note, and that's the bath tub looked to be horribly refinished with some type of coating to make it whiter or to cover stains. I didnt want to shower in it at all, and the ice machine on my floor was so loud you could hear it clear down the hall, so I just asked for a room on a different floor and it was fine. The staff was very nice, and my check-in went smoothly."

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

"Staff was wonderful room was clean. Everything was spectacular."

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

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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)
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- [RV Parks in Winter Park ](https://expedia.com/Winter-Park-RV-Parks.d7902-aaRVParks.Travel-Guide-Accommodation)
- [Riads in Winter Park ](https://expedia.com/Winter-Park-Riads.d7902-aaRiads.Travel-Guide-Accommodation)
- [Castles in Winter Park ](https://expedia.com/Winter-Park-Castles.d7902-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

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

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

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

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

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

### Expedia's Latest Trends

Hotels

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

Flights

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

Cars

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

Activities

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

Packages

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

Vacation Rentals

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

General

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

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