Winter Oaks Rentals
From $270 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 $270 per night (USD)VRBO
From $217 per night (USD)Expedia
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 $217 per night (USD)Expedia
From $211 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 $211 per night (USD)VRBO
From $346 per night (USD)Expedia
~ 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 $346 per night (USD)Expedia
From $162 per night (USD)VRBO
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 ...
From $162 per night (USD)VRBO
From $337 per night (USD)Expedia
Downtown Winter Garden bungalow with private putting green and fire pit
- 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 $337 per night (USD)Expedia
From $432 per night (USD)VRBO
Updated 4-Bedroom Winter Garden House In Golf Cart District 20 Min From Disney
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Stay less than 1 mile away from downtown Winter Garden which is the cutest downtown with many shops and restaurants, whi ...
From $432 per night (USD)VRBO
From $227 per night (USD)Expedia
Relaxing retreat w/ pool & BBQ grill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to your relaxing Winter Garden retreat - a cozy base near top attractions, perfect for families & smal ...
From $227 per night (USD)Expedia
From $279 per night (USD)VRBO
1921 2BD/1BTH Bungalow - Historic Winter Garden, Steps to Plant St, Dogs Welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the Historic District of downtown Winter Garden, this restored 1921 Bungalow is just a block to Plant Street ...
From $279 per night (USD)VRBO
From $145 per night (USD)Expedia
Lovely Studio Apt #1 in Downtown Winter Garden, by Bike Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $145 per night (USD)Expedia
From $158 per night (USD)VRBO
Cozy Studio Apt #5 by Bike Trail & Historic Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $158 per night (USD)VRBO
From $154 per night (USD)Expedia
Large Studio Apt #8 by Bike Trail & Historic Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Private studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Gard ...
From $154 per night (USD)Expedia
From $151 per night (USD)VRBO
Studio Apt #3 in Historic Downtown Winter Garden, across from the Bike Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden attra ...
From $151 per night (USD)VRBO
From $190 per night (USD)Expedia
Cute Studio Apt #2 by Bike Trail & Historic Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $190 per night (USD)Expedia
From $151 per night (USD)VRBO
Chic Studio Apt #4 by Bike Trail & Historic Downtown Winter Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $151 per night (USD)VRBO
From $145 per night (USD)Expedia
Efficiency Apt #6 Near Downtown & Bike Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cozy studio apartment across from the scenic West Orange Bike Trail and a short walk to historic downtown Winter Garden ...
From $145 per night (USD)Expedia
From $304 per night (USD)VRBO
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 $304 per night (USD)VRBO
From $138 per night (USD)Expedia
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 $138 per night (USD)Expedia
From $175 per night (USD)VRBO
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 $175 per night (USD)VRBO
From $267 per night (USD)Expedia
House 2 Bedrooms /2 full bathrooms Downtown Winter Garden
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Full renovated house in downtown Winter Garden FL. Welcome to your ideal urban retreat in the h ...
From $267 per night (USD)Expedia
From $286 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 $286 per night (USD)VRBO
From $325 per night (USD)Expedia
Dtwn Winter Garden Home: 12 Mi to Disney!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Whether you’re looking for a Disney vacation or a charming city escape, this Winter Garden vacation rental is perfect fo ...
From $325 per night (USD)Expedia
From $215 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 $215 per night (USD)VRBO
From $131 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 $131 per night (USD)VRBO
From $515 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 $515 per night (USD)VRBO
From $511 per night (USD)Expedia
WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 ...
From $511 per night (USD)Expedia