Winter Garden Holiday Rentals
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Our top choices for Winter Garden holiday rentals

Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
Monarch Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly HomesWinter Garden
10.0 out of 10, Exceptional, (2)
The price is HK$1,291
HK$2,371 total
includes taxes & fees
7 Jan - 8 Jan 2026

Pool, Gym, Near Parks | King Bed | Pet-Friendly
Pool, Gym, Near Parks | King Bed | Pet-FriendlyWinter Garden
The price is HK$933
HK$2,333 total
includes taxes & fees
7 Jan - 8 Jan 2026

Family Fun Condo: Pool, Sauna—near Disney
Family Fun Condo: Pool, Sauna—near DisneyWinter Garden
The price is HK$731
HK$2,163 total
includes taxes & fees
6 Jan - 7 Jan 2026

The price is HK$778
HK$2,246 total
includes taxes & fees
28 Dec - 29 Dec

Fire Pit & Yard: Updated Winter Garden Home!
Fire Pit & Yard: Updated Winter Garden Home!Winter Garden
The price is HK$1,423
HK$3,956 total
includes taxes & fees
28 Dec - 29 Dec

The price is HK$778
HK$2,179 total
includes taxes & fees
7 Jan - 8 Jan 2026

Learn how to camp RV style in this Lux RV which sleeps up to 8 people.
Learn how to camp RV style in this Lux RV which sleeps up to 8 people.Winter Garden
The price is HK$1,050
HK$1,805 total
includes taxes & fees
26 Dec - 27 Dec

Upstay Amazing Disney Condo w Patio Sleeps 6
Upstay Amazing Disney Condo w Patio Sleeps 6Winter Garden
The price is HK$797
HK$2,081 total
includes taxes & fees
12 Jan - 13 Jan 2026
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.
Top Winter Garden Hotel Reviews

Rosen Inn at Pointe Orlando
10/10 Excellent
Find out more about Winter Garden
Search for holiday rentals in Winter Garden on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Garden using one of the methods below:
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Look no further and take a look at our great range of rental properties in Winter Garden!

















































































