A two-story house with a balcony, surrounded by lush greenery and trees.

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Our top choices for Winter Park villas

1. Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College

Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
Winter Park
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay .. was clean and had all the amenities"
United States
Ayman
The price is NZ$550
includes taxes & fees
18 Nov - 19 Nov
Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College

2. SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging

SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
College Park
10.0 out of 10, Exceptional, (31 reviews)
"Great space! Was very comfortable "
United States
Judah E.
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging

3. Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Altamonte Springs
9.4 out of 10, Exceptional, (8 reviews)
"Enjoyed my stay, was super quiet, and very conveniently located to everywhere I needed to go in Seminole County. The host was great with communication and provided everything I needed to have a great stay."
United States
Brian
The price is NZ$319
includes taxes & fees
16 Nov - 17 Nov
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

4. Family Vacation Home Near Disney With Resort Pool

Family Vacation Home Near Disney With Resort Pool
3.0 star property
Orlando
The price is NZ$668
includes taxes & fees
22 Nov - 23 Nov
Family Vacation Home Near Disney With Resort Pool

5. 4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando

4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
Orlando
10.0 out of 10, Exceptional, (4 reviews)
"Overall it was great stay. Initially there was an issue with the door when we checked in, but the host fixed it write away. The house was very clean and had everything we needed plus more. I would definitely book again."
United States
Silvia R.
The price is NZ$1,113
includes taxes & fees
17 Nov - 18 Nov
4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando

6. At Lakes Upscale Villa/Next to Downtown Orlando

At Lakes Upscale Villa/Next to Downtown Orlando
Lake Davis - Greenwood
10.0 out of 10, Exceptional, (35 reviews)
"Very nice place and hope to stay there again someday"
United States
Wilbur B.
At Lakes Upscale Villa/Next to Downtown Orlando

7. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
Amazing Spider | Disney, Slides & River

8. The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly!
4.0 star property
Windermere
The price is NZ$1,026
includes taxes & fees
16 Nov - 17 Nov
The Farm House - Great Location + Pet Friendly!

9. Shiny Legendary | Disney, River & Slides

Shiny Legendary | Disney, River & Slides
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Had some confusion with the address but the host was super quick to respond, apologize, and fix the problem. Great location. Super cute rooms. Clean. Host had lots of essentials already at the house for us. Any question or concern we had was responded to quickly and thoroughly. "
United States
Aren B.
Shiny Legendary | Disney, River & Slides

10. Power Up Palace | Disney, River & Slides

Power Up Palace | Disney, River & Slides
Kissimmee
The price is NZ$549
includes taxes & fees
19 Nov - 20 Nov
Power Up Palace | Disney, River & Slides

11. Waves & Wishes | Moana Inspired 2BR Near Disney

Waves & Wishes | Moana Inspired 2BR Near Disney
Kissimmee
The price is NZ$471
includes taxes & fees
16 Nov - 17 Nov
Waves & Wishes | Moana Inspired 2BR Near Disney

12. Family 5BR w/ Pool & Grill Near Disney Magic

Family 5BR w/ Pool & Grill Near Disney Magic
Kissimmee
The price is NZ$956
includes taxes & fees
29 Nov - 30 Nov
Family 5BR w/ Pool & Grill Near Disney Magic

13. Lakefront Villa at a Prime Location

Lakefront Villa at a Prime Location
Orlando
9.2 out of 10, Wonderful, (70 reviews)
"From check in to check out everything was seamless. Very clean place and clean environment. Highly recommended."
United States
Madeen
Lakefront Villa at a Prime Location

14. 4,800 sf Estate | Pool, Lake, Weddings and Events

4,800 sf Estate | Pool, Lake, Weddings and Events
Orlando
9.6 out of 10, Exceptional, (33 reviews)
"Loved that Lake Lucy was pet friendly so our dogs could be a part of our wedding day! The house property was amazing and we wish we could have stayed longer!"
United States
Krysta P.
The price is NZ$2,496
includes taxes & fees
3 Dec - 4 Dec
4,800 sf Estate | Pool, Lake, Weddings and Events

15. 7BR Lakefront | Pool & Hot Tub

7BR Lakefront | Pool & Hot Tub
Edgewood
9.8 out of 10, Exceptional, (22 reviews)
"Check in was very easy and the location was great, close to everything we wanted to do.The property had lots to offer and was in a nice quiet neighborhood."
United States
Omer H.
The price is NZ$1,506
includes taxes & fees
16 Nov - 17 Nov
7BR Lakefront | Pool & Hot Tub

16. Storey Lake Resort~Heated Pool~Brand New~Designer

Storey Lake Resort~Heated Pool~Brand New~Designer
Kissimmee
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay. Host was very attentive and responded back quickly anytime we had a question before or during our stay. Resort amenities were wonderful and location was great! We would stay again! "
United States
Amber K.
The price is NZ$781
includes taxes & fees
17 Nov - 18 Nov
Storey Lake Resort~Heated Pool~Brand New~Designer

17. Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly!
4.0 star property
Windermere
8.0 out of 10, Very good, (1 review)
"Good house for a great price. Great location. Need to change the AC more often."
United States
Mercedes
The price is NZ$1,101
includes taxes & fees
17 Nov - 18 Nov
Rustic Hideaway - Great Location + Pet Friendly!

18. New Vista Cay Home | Universal & Convention

New Vista Cay Home | Universal & Convention
Orlando
The price is NZ$730
includes taxes & fees
20 Nov - 21 Nov
New Vista Cay Home | Universal & Convention

19. 3BR Townhouse Right in Front of Epic Universe!

3BR Townhouse Right in Front of Epic Universe!
Orlando
9.6 out of 10, Exceptional, (16 reviews)
"Easy access for all we did the week we stayed. Great rooms, it was wonderful to be so comfortable."
United States
Hal J.
3BR Townhouse Right in Front of Epic Universe!
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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Top Winter Park Hotel Reviews

Find out more about Winter Park

Winter Park Villas information

Number of reviews
184
Accommodation
1448 Villas
Lowest Price
NZ$319
Highest Price
NZ$2,496

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.

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