Winter Oaks Rentals
From $204 per night (USD)VRBO
Walk to Dtwn: Winter Garden Home w/ Patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled among a wealth of historical attractions, live entertainment, and outdoor recreation awaits ‘The Strawberry Hous ...
From $204 per night (USD)VRBO
From $182 per night (USD)VRBO
Walkable Winter Garden Bungalow: 3 Blocks to Dtwn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the historical highlights of Winter Garden just steps from your door when you stay at ‘The Bungalow at The Stra ...
From $182 per night (USD)VRBO
From $162 per night (USD)VRBO
16 Mi to Disney: Cottage w/ Deck in Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Adventures big or small await at this 1-bedroom, 1-bathroom vacation rental in Winter Garden! This newly renovated cotta ...
From $162 per night (USD)VRBO
From $219 per night (USD)VRBO
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your Winter Garden retreat begins at this 2-bedroom, 1-bathroom vacation rental cottage offering old Florida charm, hist ...
From $219 per night (USD)VRBO
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Adorable 1-bedroom right on the bike trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy all that Historic Downtown Winter Garden has to offer in this centrally located apartment home. The West Orange Co ...
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From $146 per night (USD)Expedia
Quaint 1Br/Ba entire guest house in heart of Hist. Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Experience Winter Garden like a local in this 1-bedroom apartment. Private Dwelling, personal covered parking, picturesq ...
From $146 per night (USD)Expedia
From $166 per night (USD)VRBO
Experience charming downtown Winter Garden! 1 block from it all!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 1920's home in the heart of downtown Winter Garden has everything you need! The home has 2 bedrooms, one with a ki ...
From $166 per night (USD)VRBO
From $232 per night (USD)Expedia
House with large deck, walking distance to Historic Downtown Winter Garden
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This completely renovated 2/2 Bungalow is the essence of the Winter Garden experience. Large, inviting living room with ...
From $232 per night (USD)Expedia
From $112 per night (USD)VRBO
2nd Floor Studio Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your ideal urban retreat in the heart of Downtown Winter Garden. Situated just steps away from the bustling d ...
From $112 per night (USD)VRBO
From $116 per night (USD)Expedia
First floor apartment Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your ideal urban retreat in the heart of Downtown Winter Garden. Situated just steps away from the bustling d ...
From $116 per night (USD)Expedia
From $275 per night (USD)VRBO
Mid Century Hipster
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious and professionally decorated 3/2 on huge fenced lot with large shade trees in front. Plenty of room for both sm ...
From $275 per night (USD)VRBO
From $113 per night (USD)Expedia
Cute & Cozy in Winter Garden FL.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
This memorable place is anything but ordinary. Conveniently located in Central Florida with many attractions nearby. A m ...
From $113 per night (USD)Expedia
From $224 per night (USD)VRBO
Dtwn Winter Garden Home: 12 Mi to Disney!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Whether you’re looking for a Disney vacation or a charming city escape, this Winter Garden vacation rental is perfect fo ...
From $224 per night (USD)VRBO
From $103 per night (USD)Expedia
Cozy Studio in Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Historic Downtown Winter Garden location with Disney & Universal Minutes Away! Charming studio in Downtown Winter Garde ...
From $103 per night (USD)Expedia
From $190 per night (USD)VRBO
Just Renovated! Cozy 2BR Close to Disney
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Located in Winter Garden, enjoy what this 2-bedroom mobile home has to offer. With 1 queen bed, 1 full bed, and 1 twin b ...
From $190 per night (USD)VRBO
From $341 per night (USD)Expedia
(381) Fantastic Home Near Disney 5BD/5BT/14P
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Your Dream Vacation Home! Step into this modern five-bedroom home, nestled in the exclusive Encore Resort (n ...
From $341 per night (USD)Expedia
From $242 per night (USD)VRBO
Enchanted 2 Bedroom Home near Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This fully furnished villa/duplex is a perfect Orlando/Winter Garden stay! This home gives you the plenty of comfort an ...
From $242 per night (USD)VRBO
From $117 per night (USD)Expedia
Enchanted TINY HOME near Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your WG experience begins at this enchanted tiny home. Either hideaway at this little retreat with what you need to rela ...
From $117 per night (USD)Expedia
From $156 per night (USD)VRBO
LUX BROWNSTONE in downtown Winter Garden FL 6 month minimum stay required
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This special place is close to everything. Just a few minutes walk to the coffee shops where you can enjoy a quite mor ...
From $156 per night (USD)VRBO
From $266 per night (USD)VRBO
Fire Pit & Yard: Updated Winter Garden Home!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The best of Winter Garden awaits you at this lovely 2-bedroom, 2-bathroom vacation rental! Located near top attractions ...
From $266 per night (USD)VRBO
From $537 per night (USD)VRBO
WATERFRONTWntrGdnHSE VIEWS Dock Wildlife 13mi Disn
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 b ...
From $537 per night (USD)VRBO