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)

![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)

![Studio | Bathroom](https://images.trvl-media.com/lodging/125000000/124510000/124504400/124504382/ed5fecda.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)

$149 nightly

$167 total

Mar 19 - Mar 20

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)

![Standard Apartment | 2 bedrooms, desk, free WiFi](https://images.trvl-media.com/lodging/100000000/99360000/99354400/99354343/70ab51cf.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)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99354400/99354343/1d542eb2.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)

$269 nightly

$292 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)

![Lobby sitting area](https://images.trvl-media.com/lodging/102000000/101420000/101419400/101419314/e5a258a1.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)

![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)

### Aparthotel in Orlando

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

8.4/10

Very Good

(1,760 reviews)

"Great place and good breakfast "

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

Suleidy

$94 nightly

$106 total

Apr 9 - Apr 10

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/d44c74b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/119200000/119199600/119199504/3dec2124.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

Mar 20 - Mar 21

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 | Private kitchen](https://images.trvl-media.com/lodging/114000000/113160000/113158900/113158893/e435191d.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)

### Vacation Home in Kissimmee

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

$412 nightly

$468 total

Mar 18 - Mar 19

Total with taxes and fees

[](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/119000000/118940000/118938800/118938718/743ca2ac.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)

### Apartment in Ventura

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

$172 nightly

$194 total

Apr 3 - Apr 4

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 | 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)

![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)

### 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

$135 nightly

$151 total

Mar 18 - Mar 19

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)

![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)

![Outdoor pool](https://images.trvl-media.com/lodging/120000000/119160000/119157700/119157665/fd696ffe.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

$113 nightly

$129 total

Mar 24 - Mar 25

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)

![Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/w4032h3011x0y0-289a1fa6.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)

"Cute little cottage with basic amenities. Very convenient location to get to Sanford airport. Would definitely stay again. "

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

Jacob

$140 nightly

$157 total

Mar 19 - Mar 20

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)

![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 | 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

Apr 6 - Apr 7

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 | 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)

![Lobby](https://images.trvl-media.com/lodging/125000000/124370000/124365700/124365680/w2499h1664x1y1-30ac7a7e.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)

### Apartment in Orlando

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

$303 nightly

$343 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)

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

![Standard Apartment | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/e1a32506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### 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 18 - Mar 19

Total with taxes and fees

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

![Front of property](https://images.trvl-media.com/lodging/124000000/123110000/123108700/123108673/7f93cd9a.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)

![Interior](https://images.trvl-media.com/lodging/124000000/123110000/123108700/123108673/910a113a.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)

### Apartment in Orlando

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

$228 nightly

$240 total

Mar 24 - Mar 25

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/b54d3a4c.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) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/03c563d3.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 18 - Mar 19

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/b4ed61fe.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/w2998h1999x2y2-68faaed2.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 in Ventura

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

$205 nightly

$231 total

Mar 17 - Mar 18

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)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355400/99355379/91a9da73.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)

![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)

### 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)

![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 | 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)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/13800/13780/eeb74d5f.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)

### Aparthotel in International Drive District

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

8.0/10

Very Good

(2,231 reviews)

"Staff was very helpful. "

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

Ulrica

$125 nightly

$141 total

Mar 23 - Mar 24

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 | 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, 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 in Kissimmee

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

$548 nightly

$622 total

Mar 18 - Mar 19

Total with taxes and fees

[](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)

![Point of interest](https://images.trvl-media.com/lodging/1000000/20000/17800/17739/w3838h2563x0y0-7461da02.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

(2,534 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=2026-03-30&endDate=2026-03-31&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&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=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=HOUSE_BOAT)

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## Top Winter Park Hotel Reviews

![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 location, friendly staff, and overall good stay. "

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

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

### Rosen Inn at Pointe Orlando

8/10 Good

"Didn't do pool. Was unaware of airport shuttle "

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

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

### CoCo Key Hotel and Water Resort 

8/10 Good

"En general están bien, pero muchas áreas sí se ve que están descuidadas necesitan renovar "

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

10/10 Excellent

"Very Clean "

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

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

### Universal's Cabana Bay Beach Resort

6/10 Okay

"The line to check in only had 5 people in front of me but it took 45 minutes to check in. The room was decent but showed wear and some mold/rust in the bathroom Resort overcharged heavily for everything. $4.50 for a cup of hot water "

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

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

### Hyatt Regency Orlando International Airport

10/10 Excellent

"The staff was a very nice goddess into our room four hours earlier than check-in. I love the fact that I could see the TSA check in from my room talk about convenient. I definitely will stay at this property again and will recommend it to everybody traveling to Orlando. "

[](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

6/10 Okay

"Th second I walked into my room I was disappointed.The floors are all separated, scratched all over the floor as if Wolverine stayed there before us.Rugs were extremely wet and smelled musty. The bunk bed had missing bolts and some were halfway out. The sink was clogged with tons and tons of hair. Room service tried fixing the issues with cleaning the sink and mopping but the floors were still super dirty, we couldn’t wear socks or be barefoot, we had to stay wearing our shoes while inside our room- noted to travel with slippers moving forward. The buffet is not worth the $25 per person either. The pool amenities weren’t as listed on the website. And the paying to park was the cherry on top. Just not what I expected based off of the website"

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

"Please post your hours for your food locations. It was a mystery. Had to walk up to the door to see if things were open or not."

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

4/10 Poor

"The resort is definitely dated and needs some attention. People were banging on our door at 1:00 AM and wouldn’t stop. This was followed by housekeeping banging on the door and hollering at 9:30 AM despite a do not disturb sign hanging on the door. Would never stay there again."

[](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)
- [Aparthotels in Winter Park ](https://expedia.com/Winter-Park-Apart-Hotels.d7902-aaApartHotels.Travel-Guide-Accommodation)
- [Town Houses in Winter Park ](https://expedia.com/Winter-Park-Town-Houses.d7902-aaTownHouses.Travel-Guide-Accommodation)
- [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)
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- [Castles in Winter Park ](https://expedia.com/Winter-Park-Castles.d7902-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

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- [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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