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Featured Villas in Winter Park

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (346)
"My family enjoyed your property after having spent 4 days at Disney. We loved the location as it was and end unit with no unit behind us. My two issues were the cost to rent a gas grill. We had to pay for a full week when we only had the grill for three days. My only other issue was that I thought the pool/Lani and the area outside of the Lani could have been cleaner. All and all it was a great stay and I would recommend it to anyone! Thank you!"
Lakeview Luxury Villa with Everything

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (399)
"We had plenty of space and the kids were always entertained. The community pool is great for kids of all ages. And the personal pool and hot tub got a lot of use, too. We had no complaints. Would recommend! "
Modern Luxury Villa with Everything

Lakeview Luxury Villa with Everything

10.0 out of 10, Exceptional, (81)
"Very good place to stay with a lot of people. Many items provided for use (towels, small appliances, etc.). Would be helpful to have more cooking items like pans, cooking utensils, food storage containers, etc. Dishwasher bottom rack does not fit appropriately and makes moving rack in and out very difficult."
Lakeview Luxury Villa with Everything

Ultimate Lakeview Villa with Everything!

9.8 out of 10, Exceptional, (347)
"THis is our second stay with Diamond. Everything was absolutely fantastic. The home was a beautiful as pictured and the pool was perfect for the kids to hang out in between our excursions. We look forward to returning again soon."
Ultimate Lakeview Villa with Everything!

Modern Luxury Villa with Everything

9.6 out of 10, Exceptional, (219)
"Check in was easy, David and the team did a great Job. House was very nice, plenty of things to do. Will be staying here again on our next trip"
Modern Luxury Villa with Everything

Ultimate Lakeview Villa with Everything!

9.4 out of 10, Exceptional, (106)
"We had a wonderful stay! The house was exactly as it was described and had everything we needed for our big family get together. We loved the access to the clubhouse. Easy check in, great location and excellent communication with the property manager. Would definitely recommend! "
Ultimate Lakeview Villa with Everything!

Beautiful lake view villa

9.2 out of 10, Wonderful, (75)
"The house was what we expected from the pictures in the listing, very comfortable for 5 of us. With the 2 separate living rooms everyone had their own space. The pool area was perfect. We heated the pool so it was nice and warm. There was lots of birds on the pond for us to enjoy. Would definitely book again"
Beautiful lake view villa

****** Close to Disney and Universal*******

9.8 out of 10, Exceptional, (94)
"This is a great property!The price is much more affordable than other comparable properties. The unit is clean and well cared for, the amenities of the pool, playground and clubhouse were a welcome break from the Disney parks. Speaking of parks, you are in closer proximity, only takes about 15 minutes to get there, as well as shopping opportunities are close.The communication from the owner is fantastic, and if you are a first responder you get a great deal.The only small notes are the oven is a...
****** Close to Disney and Universal*******

Lakeview Luxury Villa with Everything!

9.6 out of 10, Exceptional, (86)
"Great place and were treated fairly. Will come back. "
Lakeview Luxury Villa with Everything!

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

9.6 out of 10, Exceptional, (22)
"great locationgetting a little tired"
Storey Lake *10 mim -> Disney * Modern 4Bd/3Ba

Walk to Lake: Stunning Central Florida Home!

10.0 out of 10, Exceptional, (45)
"Was great to use the property for a few days with our family. it had everything we needed. "
Walk to Lake: Stunning Central Florida Home!

Villa in Kissimmee next to Disney!

8.2 out of 10, Very good, (20)
"Great location for where we needed to be everyday. House was nice. Only complaint was the sticky floor ( whatever the cleaning people use I don't think they use enough water with the solution) and the bottom of the stove wasn't cleaned inside. I would definitely stay again if needed. "
Villa in Kissimmee next to Disney!

Lakeview Luxury Villa in Storey Lake

9.8 out of 10, Exceptional, (23)
"Great property for multi families. Big clean property. Great pool . You can see alligators outside the lake "
Lakeview Luxury Villa in Storey Lake

Free Shuttle,Official Encore Water Park,XBOX,Movie,Games,Cage,Pool/Spa,Star Wars

9.8 out of 10, Exceptional, (76)
"Great stay, excellent clean property."
Free Shuttle,Official Encore Water Park,XBOX,Movie,Games,Cage,Pool/Spa,Star Wars

Unbeatable Location: Your Dream Villa Next to SeaWorld

9.4 out of 10, Exceptional, (55)
"Unit was as described. However, could not get the coffee maker to work and the tv remote did not work."
Unbeatable Location: Your Dream Villa Next to SeaWorld

Modern Luxury Villa in Storey Lake

9.4 out of 10, Exceptional, (39)
"Had a great day at this property. "
Modern Luxury Villa in Storey Lake

Resort style family friendly vacation villa

9.6 out of 10, Exceptional, (7)
"Great location and everything is functional. The property just needs some TLC to fix it up and replace some of the stains. "
The price is NZ$669
includes taxes & fees
13 May - 14 May
Resort style family friendly vacation villa

Vista Cay Modern

4.0 star property
10.0 out of 10, Exceptional, (2)
"Es una muy buena opción para una família de hasta 6 personas. Es una urbanización en una muy buena ubicación, segura y con buenas instalaciones (la piscina está en remodelación). Hay todo en la casa que se necesita para una família. "
Vista Cay Modern

6B/5B Estate on 2+ Acres W/Pool, Guesthouse, Theater & More

9.8 out of 10, Exceptional, (34)
"The house was nice and in a great location. 5 bedrooms in the main house then a couple in the guest house made it easy to fit the 12 adults we had staying. Would definitely book this house again if we return to the same area. "
6B/5B Estate on 2+ Acres W/Pool, Guesthouse, Theater & More

Perfect family two story Villa 8 near SeaWorld

9.6 out of 10, Exceptional, (72)
"Loved that the location is close to all park attractions and shopping. Also great perk of having transportation to Disney world helpful with saving costs on parking although makes for a long day in the sun but nonetheless an amazing perk. Very nice home and great for family would definitely love to book again if planning another trip around this area :) "
Perfect family two story Villa 8 near SeaWorld
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

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very good, (8584)
"The pool was beautiful as well as the property! We will be going back 🌴"
The price is NZ$304
includes taxes & fees
20 Apr - 21 Apr
Lake Buena Vista Resort Village & Spa

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1873)
"Nice, but could use improvement on bathroom maintenance. "
The price is NZ$395
includes taxes & fees
20 Apr - 21 Apr
Florida Hotel & Conference Center in the Florida Mall

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very good, (1023)
"Next time I be in Orlando I will stay here again. "
The price is NZ$129
includes taxes & fees
20 Apr - 21 Apr
The View Studio Suites and Event Venue
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

What is there to do near my villa in Winter Park?
Whatever you love to do, Winter Park has loads of things to keep you going. Winter Park Country Club, Crealde School of Art and Winter Park Village are on most travellers’ agendas. Don’t leave without exploring Casa Feliz Historic Home Museum, Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens either. With Expedia’s Winter Park hotel deals, you can see more neat attractions like these with the cash you save.