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)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124510000/124504400/124504382/7d8f8b9b.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)

![Interior](https://images.trvl-media.com/lodging/125000000/124510000/124504400/124504382/33780020.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)

![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 | 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)

![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)

$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)

![Exterior](https://images.trvl-media.com/lodging/102000000/101420000/101419400/101419314/91d4aa39.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)

### Aparthotel in Orlando

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

8.4/10

Very Good

(1,770 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/ef7280ac.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 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/114000000/113160000/113158900/113158893/9543cf08.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)

$551 nightly

$626 total

Apr 17 - Apr 18

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/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 | 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 | Living area | 60-inch LED TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/100000000/99360000/99354200/99354105/bb9facf4.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)

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

![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)

![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)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/c6a2da7b.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

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)

![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)

![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)

### 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)

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

![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)

$292 nightly

$331 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/100000000/99360000/99354600/99354524/34096aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### 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)

![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)

![Interior](https://images.trvl-media.com/lodging/124000000/123110000/123108700/123108673/910a113a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123110000/123108700/123108673/616a6a6b.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 in Orlando

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

$241 nightly

$252 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) | 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)

![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/b54d3a4c.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/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/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/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)

$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/100000000/99360000/99355400/99355379/263b4fc2.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)

### 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 | 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

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)

![Premium Suite, 2 Bedrooms | Living area | 32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/20000/13800/13780/1d826877.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)

### 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

$124 nightly

$140 total

Apr 15 - Apr 16

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/91000000/90320000/90311900/90311840/4b451942.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 | Dining](https://images.trvl-media.com/lodging/91000000/90320000/90311900/90311840/b3c11e82.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)

$533 nightly

$605 total

Mar 19 - Mar 20

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)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17800/17739/d5ee5eac.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=2026-04-01&endDate=2026-04-02&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&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=2026-06-16&d1=2026-06-16&endDate=2026-06-19&d2=2026-06-19&lodging=HOUSE_BOAT)

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## Top Winter Park Hotel Reviews

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

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

8/10 Good

"It’s great that hotel has a shuttle bus to Universal parks."

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

"Excellent hotel"

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

"Wasn't a good experience. Waited in line over an hour to check in. We got to our room and we literally had no wash cloths, no hand towels and no bath towels. There was only one pillow on the bunk bed and no blanket. We asked for all those items and we got everything in a little over an hour except for the wash cloths and hand towels. Then when I laid my head on the pillow I felt something in the pillow case and it had someone's driver's license in it so now I know the room must not have been cleaned since the pillow case was never removed and replaced with a clean one and to top it off the elevator didn't work and we were on the 6th floor. My sons girlfriend had back surgery and has numerous metal rods in her back so trying to bring luggage etc. up all those flights of stairs was not easy. Overall experience I would never stay here again. After seeing the driver's license of the person that was last laying his head on the same pillow as me without a clean pillowcase was an uneasy feeling to say the least. I don't understand why our room was not cleaned and stocked with linens after checking in at 6pm and the early 10am check out is a bit early considering your check in starts at 4pm and technically don't get to your room for at least an hour later. "

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

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

### Universal's Cabana Bay Beach Resort

10/10 Excellent

"Clean room, excellent premises"

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

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

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

8/10 Good

"Room was pretty clean, staff was kind . Pool area was great, and some other amenities for my kids to take in. "

[](https://expedia.com/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.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 place to stay and very close to all Disney attractions. "

[](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

10/10 Excellent

"Clean room, nice price "

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

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

### Coco Key Hotel & Water Park Resort

8/10 Good

"Did not use it "

[](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!

6/10 Okay

"Yes"

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