Winter Garden Vacation Rentals

Compare 6 vacation rentals.
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Make Winter Garden your next getaway

Winter Garden, FL vacation rentals

Explore Winter Garden cottages, house rentals, and more

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Cottages

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House rentals

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Winter Garden vacation rentals for every getaway

Popular
Dog-friendly Internet Electric vehicle charger
Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!

House in Winter Garden

$336 avg / night

3.0 (2)
Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

House in Winter Garden

$211 avg / night

5.0 (17)
16 Mi to Disney: Cottage w/ Deck in Winter Garden

16 Mi to Disney: Cottage w/ Deck in Winter Garden

Cottage in Winter Garden

$210 avg / night

5.0 (3)
Dtwn Winter Garden Home: 12 Mi to Disney!

Dtwn Winter Garden Home: 12 Mi to Disney!

Cottage in Winter Garden

$278 avg / night

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Explore more vacation rental amenities in Winter Garden

Lake view
Water view
Waterfront
A/C
Air conditioning
Elevator
Fireplace
Washer/dryer
Balcony
Bikes

Recent Winter Garden vacation rental reviews

Love the walkability to downtown Winter Garden and the bed in the bedroom is comfortable. Big fridge and functional kitchen with pots and pans and dishes so you don't have to eat out the whole time you visit. Note there is currently no door between the bedroom and living room or bathroom and bedroom, meaning privacy is a little challenging if you have more than just one couple staying. But it was great as just a couple.
Brandy . | May 2026
Our stay at this location it was excellent. We stayed for three months. This unit has been modernized with all amenities necessary. Its grill and patio area is private and comfortable. We used it every day. This unit is centrally located to the town center. We could walk there in 5 to 10 minutes. The unit was well cleaned when we arrived. Basically it was a turnkey stay which we enjoyed very much.
Patrick . | Apr 2026
This is such a cute little cottage. This is the second time we have stayed February and March here. Owner Suzie is wonderful to work with and very quick to respond if a problem occurs. Just steps away from Plant street where wonderful dining is and the farmers market every Saturday is impressive. Nice backyard to sit and relax.
Sue . | Mar 2026
Home away from home! Well organized kitchen, comfy bed, laundry facilities, and within walking distance of Winter Garden.
Peggy . | Feb 2026
Winter Garden Frequently Asked Questions

Yes. 121 of our Winter Garden vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Winter Garden vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Winter Garden team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Winter Garden, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

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