Search Winter Park Villa Rentals from CA $344

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Check prices for these dates

Next weekend
Feb 14 - Feb 16
In two weeks
Feb 21 - Feb 23
In one month
Mar 7 - Mar 9
In two months
Apr 4 - Apr 6

Browse Select Winter Park Villas

Lakeview Luxury Villa with Everything
Pool

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (317)
"Very nice! Lots of room for everyone."
Lakeview Luxury Villa with Everything
Modern Luxury Villa with Everything
Pool

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (366)
"We had a lot of little ones to entertain between Disney days and the pool, theater and game room were a hit!!! Also like 2 minutes drive to Target, which was so convenient. Definitely going to rebook next time we go to Orlando! "
Modern Luxury Villa with Everything
Lakeview Luxury Villa with Everything
Pool

Lakeview Luxury Villa with Everything

10.0 out of 10, Exceptional, (70)
"Great property! Super fun when not at the parks. Very clean, quiet, awesome amenities. The kids really loved the arcade in the bonus room. The extra washer and dryer were a nice bonus too. The pool was clean and eventually got up to temp. Communication with the host was smooth. Would stay here again "
Lakeview Luxury Villa with Everything
Ultimate Lakeview Villa with Everything!
Pool

Ultimate Lakeview Villa with Everything!

9.4 out of 10, Exceptional, (96)
"the facility was great however the pool and hottub were underwelming. It was cold and I was told it would not heat but it warmed through the week and we got to use it after we had been there 3 days, worked great although the jets were minimal. Next day the jets did not work at all --they did come and fix that but then there was no heat. Although everything else was great we probably won't use this property again as the pool was a big draw. "
Ultimate Lakeview Villa with Everything!
Ultimate Lakeview Villa with Everything!
Pool

Ultimate Lakeview Villa with Everything!

9.8 out of 10, Exceptional, (332)
"The property, neighborhood, location, and communication with the host were fantastic. There were no unwelcome surprises and the process of checking in and out couldn’t have been easier. Will definitely use one of their properties again in the future. "
Ultimate Lakeview Villa with Everything!
Modern Luxury Villa with Everything
Pool

Modern Luxury Villa with Everything

9.6 out of 10, Exceptional, (208)
"This stay was great, and we will be keeping this listing on our list for when we return to Orlando."
Modern Luxury Villa with Everything
South Facing Pool and spa on Water Conservation Area in Gated Community
Outdoor pool, a heated pool

South Facing Pool and spa on Water Conservation Area in Gated Community

10.0 out of 10, Exceptional, (9)
"This was a very spacious house that was clean and had all the essentials for our trip. The neighborhood was very nice and the area where the home is located was quiet with nice views of the lake. The pool area was private and had plenty of room to relax whether you were swimming or just relaxing outside. No outdoor tv, but that was the only thing we would have changed. We really enjoyed the pool table upstairs and game room in the garage for extra free entertainment while we were there. This was...
South Facing Pool and spa on Water Conservation Area in Gated Community
Lakeview Luxury Villa in Storey Lake
Pool

Lakeview Luxury Villa in Storey Lake

9.8 out of 10, Exceptional, (13)
"Stayed here for a week with family. The house was very nice and advertised. The movie room and game room were big hits. Beds were comfortable. The only complaints i had was during check in our information wasn't in the system so we had to reach out to the property management company to be added in the system. Also, we had paid for the heat on the the hot tub. The hot tub never got hot. So that was extremely disappointing and not worth the money."
Lakeview Luxury Villa in Storey Lake
Family Vacation Home, Water Park+Endless Amenities
Water park

Family Vacation Home, Water Park+Endless Amenities

5.0 star property
8.8 out of 10, Excellent, (17)
"Awesome staff, super helpful. And the resort was amazing"
Family Vacation Home, Water Park+Endless Amenities
Beautiful Vacation Home steps from Disney Parks
TV

Beautiful Vacation Home steps from Disney Parks

10.0 out of 10, Exceptional, (15)
"We had a wonderful stay at your property! The house was very cozy, and the bedrooms were great—comfortable and well-appointed. The kitchen was fantastic and had everything we needed, making meal prep so easy. The pool was amazing and added so much to our stay. Overall, this was a fantastic place to stay, and its convenient location near the parks made everything even better. Thank you for hosting us!"
Beautiful Vacation Home steps from Disney Parks
Storey Lake *10 mim -> Disney * Modern 4Bd/3Ba
Outdoor pool, a heated pool

Storey Lake *10 mim -> Disney * Modern 4Bd/3Ba

9.6 out of 10, Exceptional, (19)
"Our original booking had an issue and we were upgraded to this property. We were notified day of issue, but without a beat they immediately offered another rental location of a comparable size. The upgraded location was slightly further away from theme parks, but still central between Universal, Disney, and the airport.Only hiccup of checking in was the process of getting in at the gate, however rental property agent responded immediately and helped resolve issue. Found house to be super clean...
Storey Lake *10 mim -> Disney * Modern 4Bd/3Ba
Lakeview Luxury Villa with Everything!
Pool

Lakeview Luxury Villa with Everything!

9.6 out of 10, Exceptional, (80)
"House conveniently located far enough away from chaos of Disney but close enough to take advantage of all things Orlando has to offer. House was spacious, pool and hot tub were great. We watch football and a few movies in the theatre room. Management was responsive to our questions. Overall, very pleased with our stay, felt the pictures and description were accurate and property was priced appropriately."
Lakeview Luxury Villa with Everything!
Gorgeous 4Bd Close to Disney w/ Pool @ Storey Lake 4245
Aerial view

Gorgeous 4Bd Close to Disney w/ Pool @ Storey Lake 4245

4.5 star property
8.6 out of 10, Excellent, (7)
"Superbe séjour! La maison est très bien située, près de toutes les commodités et parcs d’attraction. Piscine privée géniale. Maison bien équipée. Instructions simples et réponses rapides du locateur. La propreté de notre lit était passable. Literie avec tâches multiples. Poussières sur tous les cadres et plaintes de sol. Rideaux sales. Verrerie toutes tachées. Devrait retirer les gobelets et pots à brosses à dents car n’ont jamais été nettoyé. La compagnie de nettoyage devrait utiliser du...
Gorgeous 4Bd Close to Disney w/ Pool @ Storey Lake 4245
9 BR/5 BA Resort Villa in Storey Lake Closed to Disney
Outdoor pool

9 BR/5 BA Resort Villa in Storey Lake Closed to Disney

10.0 out of 10, Exceptional, (7)
"Great place for a large group to meet to attend a conference together. "
9 BR/5 BA Resort Villa in Storey Lake Closed to Disney
Once Upon A Time@Storey Lake-9 Bedroom Disney Haven w/ Game Room & Private Pool!
Property grounds

Once Upon A Time@Storey Lake-9 Bedroom Disney Haven w/ Game Room & Private Pool!

10.0 out of 10, Exceptional, (54)
"Our trip included 7 adults and 5 children under the age of 5. It was plenty of space for us all and we had plenty of room to let the kids play. The location of the home was great with a 10 minute walk to target and 5 min drive to Sam’s club. Lastly, the communication with Robert was fantastic before and after our stay. He was very responsive and receptive to our messages. There was an issue with an appliance and Robert promptly sent out a mechanic to try and resolve it. The only complaints of...
Once Upon A Time@Storey Lake-9 Bedroom Disney Haven w/ Game Room & Private Pool!
Ask about Early Check in! Master Bedroom on Main Floor. 10 Min Away from Disney
A heated pool

Ask about Early Check in! Master Bedroom on Main Floor. 10 Min Away from Disney

9.6 out of 10, Exceptional, (130)
"Perfect accommodations for our family to attend the Citrus Bowl. The entry combination/key does not work well and the mattresses are near the end of their life but everything else was great."
Ask about Early Check in! Master Bedroom on Main Floor. 10 Min Away from Disney
Simile · Disney Villa - Game Room - Movie Theater - Pool
Outdoor dining

Simile · Disney Villa - Game Room - Movie Theater - Pool

10.0 out of 10, Exceptional, (19)
"We were in town for a somber occasion, so we wanted a place where family could gather and hang out and where children could have a good time. This home was perfect with the lovely themed rooms that the kids enjoyed, the heated pool, and plenty of room for family and friends to gather together."
The price is CA $344
CA $1,013 total
includes taxes & fees
Feb 11 - Feb 12
Simile · Disney Villa - Game Room - Movie Theater - Pool
Perfect family two story Villa 8 near SeaWorld
Outdoor pool, a heated pool

Perfect family two story Villa 8 near SeaWorld

9.6 out of 10, Exceptional, (68)
"The property has al the commodities we needed. It was very clean and it has a perfect location. You have all parks, restaurants and everything you could need just minutes away. We had a minor issue but Chris answered and resolved it as soon as he could. Definitely recommend this place and would love to stat here when we come back. It was a great place for our first family trip with the kids to Orlando. Thanks Chris."
Perfect family two story Villa 8 near SeaWorld
Grand Opening! 9BD/5BA-Storey Lake Resort/Lake View/GameRoom
Outdoor pool, a heated pool

Grand Opening! 9BD/5BA-Storey Lake Resort/Lake View/GameRoom

10.0 out of 10, Exceptional, (5)
"We enjoyed our time immensely. The home is spacious and lots of room for our family. Grandkids loved the pool and game room. Kids bedrooms were adorable. Our granddaughter loved the Encanto room! Thanksgiving football on 120” projection TV: fantastic! Only issue is evening traffic getting thru security into the development. Just be prepared and informed it may take a few minutes waiting in line. But we would definitely stay again. Thanks for letting us borrow your home!"
Grand Opening! 9BD/5BA-Storey Lake Resort/Lake View/GameRoom
private pool/communal pool/games room/themed bedrooms
Property grounds

private pool/communal pool/games room/themed bedrooms

9.2 out of 10, Wonderful, (17)
"The property was wonderful. It is just what we expected from the listing, no surprises! We would not hesitate to stay at this property again. My granddaughter will never forget the experience. Thank you!"
private pool/communal pool/games room/themed bedrooms
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.
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Other property types in Winter Park

The View Studio Suites and Event Venue
Property entrance

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very good, (802)
"Pleasant stay"
The price is CA $116
CA $131 total
includes taxes & fees
Feb 24 - Feb 25
The View Studio Suites and Event Venue
Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very good, (8341)
"Great property to stay at and fantastic staff!! "
Lake Buena Vista Resort Village & Spa
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1733)
"The stay was great, hospitality was great."
The price is CA $285
CA $357 total
includes taxes & fees
Feb 13 - Feb 14
Florida Hotel & Conference Center in the Florida Mall
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.

Frequently asked questions

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How can I find cheap villas in Winter Park?
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What is there to do near my villa in Winter Park?
Whatever your tastes or interests, Winter Park has plenty of things to keep you busy. Albin Polasek Museum and Sculpture Gardens, Morse Museum of American Art and Winter Park History Museum are on many travelers’ schedules. Don’t forget about Hannibal Square Heritage Center, Rollins Museum of Art and Winter Park Playhouse either. With Expedia’s hotel deals in Winter Park, you’ll be able to see even more fantastic attractions like these with the money you save.