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)

$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 | 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)

![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)

### Apartment in Sanford

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

$283 nightly

$308 total

Mar 20 - Mar 21

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)

![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)

![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)

### 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

$95 nightly

$107 total

Mar 17 - Mar 18

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

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 | 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)

$426 nightly

$484 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/bf8bc9dd.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)

### 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)

![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)

![Dining](https://images.trvl-media.com/lodging/120000000/119160000/119157700/119157665/5c3e1c01.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)

![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)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/82a6ad82.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

(8 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)

![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)

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

### Apartment in Sanford

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

9.4/10

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 23 - Mar 24

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)

![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)

$305 nightly

$345 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 | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/e1a32506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Exterior](https://images.trvl-media.com/lodging/100000000/99360000/99354600/99354524/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)

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

$231 nightly

$243 total

Mar 18 - Mar 19

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/b54d3a4c.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 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/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/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-acc69296.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/100000000/99360000/99355400/99355379/263b4fc2.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)

![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)

![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)

![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)

### 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)

![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)

![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

(2,231 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 | 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, 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 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)

![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)

![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)

### 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

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)

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)

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

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

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

10/10 Excellent

"Excellent service and easy to find"

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

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

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

8/10 Good

"The staff went above and beyond I will for sure return here thank you."

[](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

8/10 Good

"Yes, the shuttle was easy to find. Staff were super helpful. "

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

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

### Lake Buena Vista Resort Village & Spa

10/10 Excellent

"Perfect equipped apartments for couples or families, pool was nice the big ship in the middle of pool is great for awesome pics. "

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

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

### Caribe Royale Orlando

10/10 Excellent

"I will definitely be back"

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

![Marriott's Grande Vista](https://images.trvl-media.com/lodging/1000000/860000/853600/853519/w4000h2662x0y0-7b7256af_y.jpg)

### Marriott's Grande Vista

10/10 Excellent

"Check in process a little frustrating but it’s vacation club so keep that in mind. Two bedroom studio definitely will accommodate 6-8 people or kids. It was like a vacation apartment with two awesome screened in balconies. Beds were the most comfortable beds out of any Marriot ( better than the jw Marriot Savannah!!) WiFi was sketchy and if your going to Disney a tad drive but the comfortable level of the room made it worth it. Self parking but they still charge 30.00 fee. We would book this place again."

[](https://expedia.com/Orlando-Hotels-Marriotts-Grande-Vista.h853519.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

"This resort has it all! The 2 bedroom units have ample space for a large family and the kitchen is very well stocked. Having laundry in the unit is such a game changer. The staff is so kind and friendly, they all are so welcoming. We ate on site a few times and enjoyed everything we ate. We loved night swimming until 11! That was such a treat for us New Yorkers "

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

"The property was really clean. We had a very comfortable stay. The pool was nice too. "

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

8/10 Good

"Bathroom sink was stopped up and the electric outlets in the lamp bases didn’t work so there was no power source near the desk. Other than that, it was fine and conveniently located nearby to where I was working. It’s annoying that you have to pay for parking, but there’s plenty of it. Lots of shopping and convenience stores nearby. I would stay 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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