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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Winter Park villas

A covered patio with a sofa, chairs, and a small table.

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 AED 448
AED 1,121 total
includes taxes & fees
18 Nov - 19 Nov
Stylish and Spacious Winter Park Retreat Close to Dining, Shopping and Rollins College
A modern building with a glass facade and a large overhang.

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.
The price is AED 474
AED 659 total
includes taxes & fees
24 Nov - 25 Nov
SAFE QUIET PRIVATE Villa - Mins to ORL/Winter Park/Eola FREE PARKING/EV Charging
A modern kitchen with white cabinets, stainless steel appliances including a refrigerator, microwave, oven, and dishwasher, a herringbone-patterned backsplash, and a tiled floor.

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 AED 298
AED 645 total
includes taxes & fees
16 Nov - 17 Nov
Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix
Interior

4. Family Townhome Near Disney w Pool & Giant Chess

Family Townhome Near Disney w Pool & Giant Chess
3.0 star property
Orlando
The price is AED 355
AED 1,387 total
includes taxes & fees
23 Nov - 24 Nov
Family Townhome Near Disney w Pool & Giant Chess
A hot tub with a view of a lake and surrounding trees.

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 AED 929
AED 2,236 total
includes taxes & fees
17 Nov - 18 Nov
4BR Villa: Lakefront Retreat with Harry Potter Game Loft near Downtown Orlando
An outdoor patio area with stone flooring, two blue chairs, a small round table, and string lights.

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, (34 reviews)
"Very nice place and hope to stay there again someday"
United States
Wilbur B.
The price is AED 988
AED 2,078 total
includes taxes & fees
16 Nov - 17 Nov
At Lakes Upscale Villa/Next to Downtown Orlando
An aerial view of a house surrounded by dense greenery, with a visible swimming pool and a paved driveway.

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

The Farm House - Great Location + Pet Friendly!
4.0 star property
Windermere
The price is AED 588
AED 2,081 total
includes taxes & fees
13 Nov - 14 Nov
The Farm House - Great Location + Pet Friendly!
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

8. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is AED 266
AED 1,111 total
includes taxes & fees
15 Nov - 16 Nov
Amazing Spider | Disney, Slides & River
A two-story house with a red door, arched windows, and a tiled roof.

9. Power Up Palace | Disney, River & Slides

Power Up Palace | Disney, River & Slides
Kissimmee
Power Up Palace | Disney, River & Slides
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

10. 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.
The price is AED 310
AED 1,129 total
includes taxes & fees
16 Nov - 17 Nov
Shiny Legendary | Disney, River & Slides
A residential area with modern houses, paved walkways, and a forest in the background.

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

Family 5BR w/ Pool & Grill Near Disney Magic
Kissimmee
The price is AED 333
AED 1,958 total
includes taxes & fees
14 Nov - 15 Nov
Family 5BR w/ Pool & Grill Near Disney Magic
A park with a pathway, palm trees, and a body of water during sunset.

12. 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
The price is AED 349
AED 811 total
includes taxes & fees
19 Nov - 20 Nov
Lakefront Villa at a Prime Location
A residential property with a swimming pool, a covered patio, and a landscaped garden.

13. 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 AED 1,250
AED 2,843 total
includes taxes & fees
18 Nov - 19 Nov
7BR Lakefront | Pool & Hot Tub
A poolside area with a covered seating area, a pool, and a view of a body of water.

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 AED 1,563
AED 4,053 total
includes taxes & fees
17 Nov - 18 Nov
4,800 sf Estate | Pool, Lake, Weddings and Events
A resort with a large swimming pool, a covered area with seating, and a building with a red roof.

15. A playful themed townhome for up to eight guests

A playful themed townhome for up to eight guests
Kissimmee
A playful themed townhome for up to eight guests
A two-story house with a garage, a covered porch, and a landscaped front yard.

16. 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 AED 588
AED 2,234 total
includes taxes & fees
17 Nov - 18 Nov
Rustic Hideaway - Great Location + Pet Friendly!
An aerial view of a resort with a central swimming pool, surrounded by multi-story buildings with balconies, and a body of water in the foreground.

17. New Vista Cay Home | Universal & Convention

New Vista Cay Home | Universal & Convention
Orlando
The price is AED 668
AED 1,554 total
includes taxes & fees
20 Nov - 21 Nov
New Vista Cay Home | Universal & Convention
A hallway with a wooden staircase, white walls, and a clock on the wall.

18. 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.
The price is AED 713
AED 1,606 total
includes taxes & fees
15 Nov - 16 Nov
3BR Townhouse Right in Front of Epic Universe!
A covered outdoor swimming pool with lounge chairs and a hot tub, surrounded by a metal frame and a view of a lake and trees.

19. Top Luxury Villa Storey Lake Mins to Disney

Top Luxury Villa Storey Lake Mins to Disney
3.0 star property
Kissimmee
The price is AED 3,076
AED 10,071 total
includes taxes & fees
16 Nov - 17 Nov
Top Luxury Villa Storey Lake Mins to Disney
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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Learn more about Winter Park

Stroll through the Morse Museum to see the world's largest collection of Tiffany glass, then boat through the Winter Park Chain of Lakes. Charming Park Avenue offers upscale shopping and outdoor cafés where you can people-watch before catching a sunset concert in Central Park.

See all hotels in Winter Park
A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.

Frequently Asked Questions

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