
Holiday Homes in Winter Park
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Our top choices for Winter Park holiday homes

1. Funky Remodeled Otown Bungalow Sleeps 8
Funky Remodeled Otown Bungalow Sleeps 8Fairview Shores
10.0 out of 10, Exceptional, (1 review)
The price is AU$370
includes taxes & fees
1 Dec - 2 Dec

2. Cozy home 5min to Park Ave and Downtown Orlando
Cozy home 5min to Park Ave and Downtown OrlandoFairview Shores
10.0 out of 10, Exceptional, (1 review)
The price is AU$407
includes taxes & fees
1 Dec - 2 Dec

3. Charming home @wp. Patio +Gazebo. close to highwys
Charming home @wp. Patio +Gazebo. close to highwysFairview Shores
5.4 out of 10, (3 reviews)
The price is AU$394
includes taxes & fees
1 Dec - 2 Dec

4. Mills House @WP. Sleeps 11 Renovated. Queen beds
Mills House @WP. Sleeps 11 Renovated. Queen bedsFairview Shores
8.0 out of 10, Very good, (2 reviews)
The price is AU$447
includes taxes & fees
1 Dec - 2 Dec

5. 3-bedroom house in quaint Winter Park with cool vibes
3-bedroom house in quaint Winter Park with cool vibesHannibal Square

6. Spacious 5-bedroom house in gorgeous Winter Park
Spacious 5-bedroom house in gorgeous Winter ParkWinter Park
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$433
includes taxes & fees
17 Nov - 18 Nov

7. Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/FenceGoldenrod
9.6 out of 10, Exceptional, (5 reviews)
The price is AU$589
includes taxes & fees
17 Nov - 18 Nov

8. Spacious 5-bedroom house in welcoming Winter Park
Spacious 5-bedroom house in welcoming Winter ParkWinter Park

9. Top 1% Modern Japandi Retreat - Jacuzzi No Fee
Top 1% Modern Japandi Retreat - Jacuzzi No FeeWinter Park
10.0 out of 10, Exceptional, (8 reviews)
The price is AU$981
includes taxes & fees
22 Nov - 23 Nov

10. Luxury Designer Home • Disney, Universal & Downtown
Luxury Designer Home • Disney, Universal & DowntownCollege Park
10.0 out of 10, Exceptional, (2 reviews)
The price is AU$900
includes taxes & fees
1 Dec - 2 Dec

11. Cute 5-bedroom,6bed house in superb Winter Park.
Cute 5-bedroom,6bed house in superb Winter Park.Winter Park
4.0 out of 10, (1 review)

12. 2/1 with private backyard in the heart of Ivanhoe
2/1 with private backyard in the heart of IvanhoeIvanhoe Village
8.0 out of 10, Very good, (16 reviews)
The price is AU$359
includes taxes & fees
16 Nov - 17 Nov

13. Stylish & Cozy King Bed Retreat @ Baldwin Park
Stylish & Cozy King Bed Retreat @ Baldwin ParkOrlando
10.0 out of 10, Exceptional, (22 reviews)

14. Sunshine Escape Guesthouse ☀
Sunshine Escape Guesthouse ☀Orlando
8.6 out of 10, Excellent, (21 reviews)
The price is AU$239
includes taxes & fees
17 Nov - 18 Nov

15. Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!
Cozy, Private, Modern 1BD/1BA Apt in College Park Home. Pet Friendly!College Park
10.0 out of 10, Exceptional, (4 reviews)
The price is AU$253
includes taxes & fees
16 Nov - 17 Nov

16. CUTE and COZY studio w/ jacuzzi!
CUTE and COZY studio w/ jacuzzi!Azalea Park
8.6 out of 10, Excellent, (10 reviews)
The price is AU$254
includes taxes & fees
17 Nov - 18 Nov

17. Studio in the heart of Orlando
Studio in the heart of OrlandoAzalea Park
9.4 out of 10, Exceptional, (6 reviews)
The price is AU$220
includes taxes & fees
16 Nov - 17 Nov

18. Private Luxury Pool / Swim up bar / Smart-home
Private Luxury Pool / Swim up bar / Smart-homeCollege Park
9.6 out of 10, Exceptional, (90 reviews)
The price is AU$702
includes taxes & fees
17 Nov - 18 Nov

19. “The Clementine” Boho Home in Orlando’s Food Scene
“The Clementine” Boho Home in Orlando’s Food ScenePark Lake - Highland
9.6 out of 10, Exceptional, (27 reviews)
The price is AU$336
includes taxes & fees
29 Nov - 30 Nov

20. Luxury Ranch 2 Master Kg Bed w/ heated Salted Pool
Luxury Ranch 2 Master Kg Bed w/ heated Salted PoolCollege Park
9.6 out of 10, Exceptional, (15 reviews)
The price is AU$1,283
includes taxes & fees
1 Dec - 2 Dec
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

Avanti International Resort
10/10 Excellent
Find out more about Winter Park
Winter Park Holiday Homes information
Number of reviews | 144 |
|---|---|
Accommodation | 5530 Holiday Homes |
Lowest Price | AU$220 |
Highest Price | AU$1,283 |



































































